Knowledge (XXG)

Oxalate

Source 📝

27: 790: 761: 1994: 2162:
reported acute oxalate nephropathy "almost certainly due to excessive consumption of iced tea" in a 56-year-old man, who drank "sixteen 8-ounce glasses of iced tea daily" (roughly 3.8 liters). The authors of the paper hypothesized that acute oxalate nephropathy is an underdiagnosed cause of kidney
2110:. Oxalic acid and oxalates can be oxidized by permanganate in an autocatalytic reaction. One of the main applications of oxalic acid is rust-removal, which arises because oxalate forms water-soluble derivatives with the ferric ion. 909:
species (also sometimes called sorrels). The root and/or leaves of rhubarb and buckwheat are high in oxalic acid. Other edible plants with significant concentrations of oxalate include, in decreasing order, star fruit
2422:
Dinnebier, Robert E.; Vensky, Sascha; Panthöfer, Martin; Jansen, Martin (2003). "Crystal and Molecular Structures of Alkali Oxalates: First Proof of a Staggered Oxalate Anion in the Solid State".
2253: 2961:
Ulmgren, Per; Rådeström, Rune (1999). "Solubility of calcium oxalate in the presence of magnesium ions, and solubility of magnesium oxalate in sodium chloride medium".
860:
units. This barrier to rotation about the C−C bond (which formally corresponds to the difference in energy between the planar and staggered forms) may be attributed to
2005:(calcium oxalate dihydrate) emerging from the amorphous central part of the stone; the horizontal length of the picture represents 0.5 mm of the figured original. 283: 3800: 3038: 2927: 3130: 2240:
oxalate(2−) (CHEBI:30623) is conjugate base of oxalate(1−) (CHEBI:46904) … oxalate(1−) (CHEBI:46904) is conjugate acid of oxalate(2−) (CHEBI:30623)
2489: 2462: 3914: 2063:. When the oxalate chelates to a single metal center, it always adopts the planar conformation. As a bidentate ligand, it forms a 5-membered 2928:"A combined experimental and modelling study on solubility of calcium oxalate monohydrate at physiologically relevant pH and temperatures" 2158: 3970: 3285: 2714: 2689: 2271: 895:
are high in oxalic acid and can contribute to the formation of kidney stones in some individuals. Other oxalate-rich plants include
248: 2926:
Ibis, Fatma; Dhand, Priya; Suleymanli, Sanan; van der Heijden, Antoine E. D. M.; Kramer, Herman J. M.; Eral, Huseyin Burak (2020).
3081: 2046: 3895: 3303: 3276: 3016: 105: 982:
in hot water typically contains only low to moderate amounts of oxalic acid due to the small mass of leaves used for brewing.
619:, no oxalic acid and only trace amounts of hydrogen oxalate exist. The literature is often unclear on the distinction between 3230: 978:) contain among the greatest measured concentrations of oxalic acid relative to other plants. However, the drink derived by 3031: 405: 3514: 225: 5262: 3931: 3605: 3325: 2163:
failure and suggested thorough examination of patient dietary history in cases of unexplained kidney failure without
2134:
Although unusual, consumption of oxalates (for example, the grazing of animals on oxalate-containing plants such as
2630:
Herbert, John M.; Ortiz, J. V. (2000). "Ab Initio Investigation of Electron Detachment in Dicarboxylate Dianions".
752:
have been identified by single-crystal X-ray diffraction: one contains a planar and the other a staggered oxalate.
574: 789: 4211: 3687: 3661: 3653: 960: 861: 600: = 1.27). The loss of the second proton, which yields the oxalate ion, has an equilibrium constant of 3024: 2194:
is a rare, inherited condition, resulting in increased excretion of oxalate, with oxalate stones being common.
817: 760: 5204: 5184: 4945: 5257: 5164: 4905: 4845: 4317: 3919: 5125: 5050: 2484:
Dinnebier, R.E.; Vensky, S.; Panthofer, M.; Jansen, M. (2003). "CSD Entry QQQAZJ03: Di-potassium oxalate".
837: 5025: 4825: 4372: 4329: 4326: 4127: 3963: 3268: 3192: 2169: 2075: 5144: 4985: 4529: 5108: 4885: 4865: 3796: 2407:
In the figure 81(1)°, the (1) indicates that 1° is the standard uncertainty of the measured angle of 81°
2191: 2186: 2052: 53: 43: 4613: 2779:
Pabuççuoğlu, Uğur (2005). "Aspects of oxalosis associated with aspergillosis in pathology specimens".
2457:
Dinnebier, R.E.; Vensky, S.; Panthofer, M.; Jansen, M. (2003). "CSD Entry WUWTIR: Di-cesium oxalate".
5005: 4965: 4925: 4805: 4250: 3858: 3437: 3392: 2639: 2511:
Clark, Timothy; Schleyer, Paul von Ragué (1981). "Conformational preferences of 34 valence electron A
2380: 2341: 2299: 570: 390: 4323: 3248: 2665: 2136: 71: 4466: 4335: 3539: 2986: 2585: 2326: 2167:(an excess of protein in the urine) and with large amounts of calcium oxalate in urine sediment. 1032: 679: 363: 117: 3701: 3104: 3099: 2900: 5252: 4764: 4426: 4264: 4194: 4167: 4160: 4141: 4063: 4042: 3956: 3783: 3554: 3544: 3534: 3529: 3524: 3499: 3072: 3059: 3051: 2978: 2949: 2878: 2837: 2796: 2761: 2710: 2685: 2681: 2669: 2439: 2267: 974: 896: 4667: 4409: 4348: 4278: 4183: 4071: 3757: 3588: 3549: 3519: 2970: 2939: 2868: 2827: 2788: 2751: 2743: 2647: 2612: 2577: 2493: 2466: 2431: 2388: 2349: 2307: 2259: 2060: 735: 566: 554: 514: 479: 452: 429: 306: 1993: 234: 157: 5070: 4578: 4516: 4442: 4225: 4175: 4090: 4024: 3561: 2014: 1651: 767: 691: 534: 350: 169: 81: 2643: 2384: 2345: 2303: 2224: 137: 5090: 4785: 4596: 4498: 4354: 4290: 4110: 4055: 3925: 3452: 3138: 3047: 2756: 2731: 2149: 2107: 1740: 1702: 1473: 845: 675: 502: 456: 399: 345: 2974: 5246: 3882: 3852: 3442: 3427: 3422: 3383: 3055: 2730:
Mitchell T, Kumar P, Reddy T, Wood KD, Knight J, Assimos DG, Holmes RP (March 2019).
2674: 2616: 2123: 1840: 384: 2990: 2589: 2210: 820:
about this bond is calculated to be roughly 2–6 kcal/mol for the free dianion,
26: 4309: 3872: 3842: 3820: 3815: 3788: 3737: 3716: 3566: 3505: 3461: 3338: 3281: 3220: 3215: 3196: 3094: 3063: 2010: 1998: 1988: 1327: 1267: 939: 915: 2857:"The role of Oxalobacter formigenes colonization in calcium oxalate stone disease" 451:
is colorless. It occurs naturally, including in some foods. It forms a variety of
214: 4652: 4550: 4367: 4313: 3995: 3742: 3670: 3639: 3571: 3472: 3466: 3456: 3359: 3153: 3143: 2747: 2290:
Dean, Philip A. W. (2012). "The Oxalate Dianion, C2O42-: Planar or Nonplanar?".
2164: 2141: 2099: 2033: 2018: 1555: 1544: 947: 841: 506: 3948: 2855:
Siener, R.; Bangen, U.; Sidhu, H.; Hönow, R.; von Unruh, G.; Hesse, A. (2013).
3847: 3764: 3747: 3732: 3711: 3696: 3691: 3634: 3619: 3593: 3583: 3578: 3432: 3401: 3333: 3313: 3291: 3180: 3164: 3160: 3109: 2792: 2393: 2368: 2353: 2002: 1885: 1817: 1784: 1754: 1665: 1578: 1022: 923: 877: 332: 148: 2982: 2953: 2263: 3835: 3830: 3810: 3805: 3752: 3706: 3680: 3675: 3624: 3482: 3405: 3369: 3343: 3308: 3296: 3258: 3253: 3243: 3205: 3175: 3170: 3148: 3114: 3089: 2174: 1958: 1921: 1862: 1717: 1436: 1290: 943: 911: 892: 873: 562: 2882: 2841: 2800: 2765: 2603:
Dewar, Michael J.S.; Zheng, Ya-Jun (1990). "Structure of the oxalate ion".
2443: 2944: 2581: 16:
Any derivative of oxalic acid; chemical compound containing oxalate moiety
3629: 3614: 3447: 3418: 3409: 3397: 3364: 3210: 2832: 2815: 2103: 1944: 1540: 1450: 1216: 1007: 979: 927: 872:
Oxalate occurs in many plants, where it is synthesized by the incomplete
2873: 2856: 3890: 3867: 3665: 3494: 3238: 1907: 1170: 1147: 1078: 1055: 955: 919: 888: 884: 836:. Such results are consistent with the interpretation that the central 674:
The oxalate anion exists in a nonplanar conformation where the O–C–C–O
448: 201: 3007:- Oxalate content of 750+ foods from university and government sources 2814:
Syed, Fahd; Mena Gutiérrez, Alejandra; Ghaffar, Umbar (2 April 2015).
2651: 2435: 2311: 3862: 2025: 1688: 1614: 1600: 1413: 1373: 1253: 1239: 905: 900: 526: 475: 2497: 2470: 398:
Except where otherwise noted, data are given for materials in their
189: 3124: 3013:- Oxalate content database based on the latest trustworthy studies 2252:
Riemenschneider, Wilhelm; Tanifuji, Minoru (2000). "Oxalic Acid".
2153: 2029: 1992: 1777: 1637: 1496: 1402: 1124: 951: 931: 615: = 4.28). These values imply, in solutions with neutral 558: 425: 128: 104: 94: 3769: 1794: 1350: 1313: 1193: 1101: 965: 935: 530: 180: 3952: 3020: 666:, and the collection of species is referred to as oxalic acid. 3010: 2145: 1533: 969: 864:
as unfavorable O−O repulsion is maximized in the planar form.
591: 529:
from oxalic acid proceeds in a stepwise manner; as for other
2009:
Excess consumption of oxalate-rich foods has been linked to
616: 510: 2106:-based drugs, avoiding the dose-limiting side-effect of 686:. When chelated to cations, oxalate adopts the planar, D 3004: 883:
Several plant foods such as the root and/or leaves of
2102:
exhibits improved water solubility relative to older
2122:, and high levels of oxalate in the urine is termed 533:, loss of a single proton results in the monovalent 3881: 3782: 3725: 3652: 3604: 3493: 3481: 3391: 3382: 3352: 3324: 3267: 3229: 3191: 3123: 3080: 3071: 2673: 1997:Scanning electron micrograph of the surface of a 708:the O–C–C–O dihedral angle is 81(1)°. Therefore, 2736:American Journal of Physiology. Renal Physiology 2486:Cambridge Structural Database: Access Structures 2459:Cambridge Structural Database: Access Structures 267:InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)/p-2 257:InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)/p-2 213: 2908:Table: Solubility product constants near 25 °C" 2705:Resnick, Martin I.; Pak, Charles Y. C. (1990). 2118:An excess oxalate level in the blood is termed 795:Planar conformation found in potassium oxalate 80: 2707:Urolithiasis, A Medical and Surgical Reference 2255:Ullmann's Encyclopedia of Industrial Chemistry 734:planes are staggered. Two structural forms of 517:, oxalic acid converts completely to oxalate. 3964: 3032: 8: 2732:"Dietary oxalate and kidney stone formation" 2285: 2283: 2417: 2415: 2413: 690:conformation. However, in the structure of 3971: 3957: 3949: 3490: 3388: 3077: 3039: 3025: 3017: 2144:or, specifically in excessive quantities, 984: 156: 18: 2943: 2872: 2831: 2755: 2392: 233: 5118: 5114: 5110: 5100: 5096: 5092: 4778: 4774: 4770: 4766: 4673: 4669: 4627: 4623: 4619: 4615: 4602: 4598: 4588: 4584: 4580: 4556: 4552: 4522: 4518: 4508: 4504: 4500: 4456: 4452: 4448: 4444: 4432: 4428: 4360: 4356: 4341: 4337: 4284: 4280: 4270: 4266: 4256: 4252: 4231: 4227: 4217: 4213: 4204: 4200: 4196: 4147: 4143: 4133: 4129: 4120: 4116: 4112: 4048: 4044: 4034: 4030: 4026: 2963:Nordic Pulp & Paper Research Journal 2605:Journal of Molecular Structure: THEOCHEM 2093: 2089: 2085: 2081: 2070: 2066: 823: 806: 802: 798: 780: 776: 772: 748: 744: 740: 730: 719: 715: 711: 704: 700: 696: 653: 637: 630: 626: 622: 540: 497: 493: 489: 485: 470: 466: 462: 434: 314: 2202: 288: 253: 4013: 2709:. W.B. Saunders Company. p. 158. 2490:Cambridge Crystallographic Data Centre 2463:Cambridge Crystallographic Data Centre 4752: 2367:Beagley, B.; Small, R. W. H. (1964). 2327:"Sodium oxalate structure refinement" 2325:Reed, D. A.; Olmstead, M. M. (1981). 2055:where it is sometimes abbreviated as 270:Key: MUBZPKHOEPUJKR-UHFFFAOYSA-L 260:Key: MUBZPKHOEPUJKR-UHFFFAOYSA-L 136: 7: 3991: 2632:The Journal of Physical Chemistry A 2159:The New England Journal of Medicine 727:symmetry structure because the two 723:is more closely approximated by a D 204: 188: 2570:Journal of Computational Chemistry 2369:"The structure of lithium oxalate" 2059:. It is commonly encountered as a 582:) for loss of the first proton is 32:The structure of the oxalate anion 14: 2975:10.3183/npprj-1999-14-04-p330-335 2781:Pathology – Research and Practice 2676:Introduction to Organic Chemistry 2074:ring. An illustrative complex is 2013:formation of metal ions, such as 3654:Direct thrombin (IIa) inhibitors 3082:Glycoprotein IIb/IIIa inhibitors 2816:"A Case of Iced-Tea Nephropathy" 2334:Acta Crystallographica Section B 2047:Transition metal oxalate complex 788: 766:Nonplanar conformation found in 759: 25: 3277:Thromboxane synthase inhibitors 2820:New England Journal of Medicine 2001:showing tetragonal crystals of 402:(at 25 °C , 100 kPa). 678:approach 90° with approximate 1: 2292:Journal of Chemical Education 1536:, leaves (4-minute infusion) 3515:Low-molecular-weight heparin 3326:Phosphodiesterase inhibitors 3239:Acetylsalicylic acid/Aspirin 2617:10.1016/0166-1280(90)85053-P 2748:10.1152/ajprenal.00373.2018 2225:"oxalate(2−) (CHEBI:30623)" 521:Relationship to oxalic acid 5279: 4754: 2184: 2156:due to oxalate poisoning. 2140:, or human consumption of 2044: 2041:As a ligand for metal ions 1986: 986:Common high-oxalate foods 862:electrostatic interactions 4015: 3988: 3909: 3487:(with some II inhibition) 2793:10.1016/j.prp.2005.03.005 2394:10.1107/S0365110X64002079 2354:10.1107/S0567740881004676 2177:may help alleviate this. 961:Tetragonia tetragonioides 396: 376: 356: 299: 279: 244: 64: 52: 42: 37: 24: 2666:Streitweiser, Andrew Jr. 2264:10.1002/14356007.a18_247 565:, monobasic oxalate, or 420:(systematic IUPAC name: 1127:, Swiss, leaves cooked 958:, New Zealand spinach ( 561:is sometimes called an 3797:Plasminogen activators 3269:Thromboxane inhibitors 3193:Prostaglandin analogue 2373:Acta Crystallographica 2170:Oxalobacter formigenes 2076:potassium ferrioxalate 2053:coordination compounds 2006: 3859:serine endopeptidases 3393:Vitamin K antagonists 2945:10.3390/cryst10100924 2680:. Macmillan. p.  2670:Heathcock, Clayton H. 2582:10.1002/jcc.540020106 2192:Primary hyperoxaluria 2187:Primary hyperoxaluria 2037:produce oxalic acid. 1996: 1983:Physiological effects 1603:, Idaho white, baked 899:("lamb's quarters"), 54:Systematic IUPAC name 3606:Direct Xa inhibitors 3438:Ethyl biscoumacetate 3304:Receptor antagonists 2861:Kidney International 2833:10.1056/NEJMc1414481 1708:1 bar (1.02 oz) 868:Occurrence in nature 571:equilibrium constant 525:The dissociation of 391:Dinitrogen tetroxide 3249:Carbasalate calcium 2874:10.1038/ki.2013.104 2867:(June): 1144–1149. 2644:2000JPCA..10411786H 2638:(50): 11786–11795. 2424:Inorganic Chemistry 2385:1964AcCry..17..783B 2346:1981AcCrB..37..938R 2304:2012JChEd..89..417D 2137:Bassia hyssopifolia 2051:Oxalate also forms 2021:for kidney stones. 1058:, stewed, no sugar 987: 818:barrier to rotation 340: g·mol 118:Beilstein Reference 21: 5263:Carboxylate anions 3936:Never to phase III 3784:Thrombolytic drugs 3500:glycosaminoglycans 3073:Antiplatelet drugs 3060:antiplatelet drugs 3011:Oxalatecontent.com 2007: 985: 406:Infobox references 377:Related compounds 19: 5240: 5239: 5234: 5233: 3979:Compounds of the 3946: 3945: 3778: 3777: 3648: 3647: 3378: 3377: 2826:(14): 1377–1378. 2652:10.1021/jp002657c 2436:10.1021/ic0205536 2312:10.1021/ed200202r 1980: 1979: 1743:, edible portion 1035:, leaves, cooked 975:Camellia sinensis 840:is regarded as a 414:Chemical compound 412: 411: 106:Interactive image 5270: 5122: 5104: 4782: 4677: 4631: 4606: 4592: 4560: 4526: 4512: 4460: 4436: 4364: 4345: 4288: 4274: 4260: 4235: 4221: 4208: 4151: 4137: 4124: 4052: 4038: 3992: 3973: 3966: 3959: 3950: 3758:Drotrecogin alfa 3738:Antithrombin III 3589:Dermatan sulfate 3562:Oligosaccharides 3491: 3389: 3125:ADP receptor/P2Y 3078: 3041: 3034: 3027: 3018: 2994: 2957: 2947: 2922: 2920: 2918: 2887: 2886: 2876: 2852: 2846: 2845: 2835: 2811: 2805: 2804: 2776: 2770: 2769: 2759: 2742:(3): F409–F413. 2727: 2721: 2720: 2702: 2696: 2695: 2679: 2662: 2656: 2655: 2627: 2621: 2620: 2611:(1–2): 157–162. 2600: 2594: 2593: 2567: 2566: 2565: 2557: 2556: 2508: 2502: 2501: 2481: 2475: 2474: 2454: 2448: 2447: 2430:(5): 1499–1507. 2419: 2408: 2405: 2399: 2398: 2396: 2364: 2358: 2357: 2331: 2322: 2316: 2315: 2287: 2278: 2277: 2249: 2243: 2242: 2237: 2235: 2221: 2215: 2214: 2207: 2148:) may result in 2097: 2073: 2061:bidentate ligand 1973:cup (4 oz) 1972: 1971: 1967: 1935: 1934: 1930: 1898: 1897: 1893: 1876: 1875: 1871: 1853: 1852: 1848: 1831: 1830: 1826: 1808: 1807: 1803: 1768: 1767: 1763: 1731: 1730: 1726: 1679: 1678: 1674: 1652:Brussels sprouts 1640:, raw with skin 1628: 1627: 1623: 1591: 1590: 1586: 1569: 1568: 1564: 1524: 1523: 1519: 1516: 1510: 1509: 1505: 1487: 1486: 1482: 1464: 1463: 1459: 1453:, diced, cooked 1427: 1426: 1422: 1401: 1400: 1396: 1393: 1387: 1386: 1382: 1364: 1363: 1359: 1341: 1340: 1336: 1304: 1303: 1299: 1281: 1280: 1276: 1230: 1229: 1225: 1207: 1206: 1202: 1184: 1183: 1179: 1161: 1160: 1156: 1138: 1137: 1133: 1115: 1114: 1110: 1092: 1091: 1087: 1069: 1068: 1064: 1046: 1045: 1041: 1021: 1020: 1016: 988: 968:. Leaves of the 859: 858: 857: 854: 848:between the two 835: 834: 833: 830: 809: 792: 783: 763: 751: 736:rubidium oxalate 733: 722: 707: 665: 664: 663: 660: 649: 648: 647: 644: 633: 607: 605: 589: 587: 567:hydrogen oxalate 552: 551: 550: 547: 531:polyprotic acids 515:aqueous solution 500: 480:dimethyl oxalate 473: 446: 445: 444: 441: 430:chemical formula 339: 326: 325: 324: 321: 307:Chemical formula 237: 217: 206: 192: 170:Gmelin Reference 160: 140: 108: 84: 29: 22: 5278: 5277: 5273: 5272: 5271: 5269: 5268: 5267: 5243: 5242: 5241: 5236: 5235: 5220: 5216: 5212: 5208: 5200: 5196: 5192: 5188: 5180: 5176: 5172: 5168: 5160: 5156: 5152: 5148: 5137: 5133: 5129: 5120: 5116: 5112: 5107: 5102: 5098: 5094: 5089: 5082: 5078: 5074: 5066: 5062: 5058: 5054: 5041: 5037: 5033: 5029: 5021: 5017: 5013: 5009: 5001: 4997: 4993: 4989: 4981: 4977: 4973: 4969: 4961: 4957: 4953: 4949: 4941: 4937: 4933: 4929: 4921: 4917: 4913: 4909: 4901: 4897: 4893: 4889: 4881: 4877: 4873: 4869: 4861: 4857: 4853: 4849: 4841: 4837: 4833: 4829: 4821: 4817: 4813: 4809: 4801: 4797: 4793: 4789: 4780: 4776: 4772: 4768: 4763: 4675: 4671: 4666: 4629: 4625: 4621: 4617: 4612: 4604: 4600: 4595: 4590: 4586: 4582: 4577: 4558: 4554: 4549: 4545: 4541: 4537: 4533: 4524: 4520: 4515: 4510: 4506: 4502: 4497: 4478: 4474: 4470: 4458: 4454: 4450: 4446: 4441: 4434: 4430: 4425: 4421: 4417: 4413: 4388: 4384: 4380: 4376: 4362: 4358: 4353: 4343: 4339: 4334: 4321: 4316: 4312: 4308: 4306: 4302: 4298: 4294: 4289: 4286: 4282: 4277: 4272: 4268: 4263: 4258: 4254: 4249: 4233: 4229: 4224: 4219: 4215: 4210: 4209: 4206: 4202: 4198: 4193: 4179: 4171: 4166: 4164: 4149: 4145: 4140: 4135: 4131: 4126: 4125: 4122: 4118: 4114: 4109: 4094: 4089: 4087: 4083: 4079: 4075: 4067: 4059: 4050: 4046: 4041: 4036: 4032: 4028: 4023: 4007: 4003: 3999: 3984: 3977: 3947: 3942: 3941: 3926:Clinical trials 3905: 3877: 3787: 3774: 3721: 3644: 3600: 3503: 3498: 3486: 3477: 3453:1,3-Indandiones 3395: 3374: 3348: 3320: 3263: 3225: 3187: 3139:Thienopyridines 3128: 3119: 3067: 3048:Antithrombotics 3045: 3001: 2960: 2925: 2916: 2914: 2907: 2898: 2895: 2893:Further reading 2890: 2854: 2853: 2849: 2813: 2812: 2808: 2778: 2777: 2773: 2729: 2728: 2724: 2717: 2704: 2703: 2699: 2692: 2664: 2663: 2659: 2629: 2628: 2624: 2602: 2601: 2597: 2564: 2561: 2560: 2559: 2555: 2552: 2551: 2550: 2548: 2546: 2542: 2538: 2534: 2530: 2526: 2518: 2514: 2510: 2509: 2505: 2498:10.5517/cc6fzcy 2483: 2482: 2478: 2471:10.5517/cc6fzf0 2456: 2455: 2451: 2421: 2420: 2411: 2406: 2402: 2366: 2365: 2361: 2329: 2324: 2323: 2319: 2289: 2288: 2281: 2274: 2251: 2250: 2246: 2233: 2231: 2223: 2222: 2218: 2209: 2208: 2204: 2200: 2189: 2183: 2132: 2116: 2095: 2091: 2087: 2083: 2079: 2072: 2068: 2064: 2049: 2043: 2015:calcium oxalate 1991: 1985: 1969: 1965: 1964: 1932: 1928: 1927: 1895: 1891: 1890: 1873: 1869: 1868: 1850: 1846: 1845: 1828: 1824: 1823: 1805: 1801: 1800: 1780:, raw, chopped 1765: 1761: 1760: 1728: 1724: 1723: 1709: 1676: 1672: 1671: 1625: 1621: 1620: 1588: 1584: 1583: 1566: 1562: 1561: 1521: 1517: 1514: 1512: 1507: 1503: 1502: 1484: 1480: 1479: 1461: 1457: 1456: 1424: 1420: 1419: 1416:greens, cooked 1398: 1394: 1391: 1389: 1384: 1380: 1379: 1361: 1357: 1356: 1338: 1334: 1333: 1301: 1297: 1296: 1293:greens, cooked 1278: 1274: 1273: 1259:20 long leaves 1227: 1223: 1222: 1219:greens, cooked 1204: 1200: 1199: 1181: 1177: 1176: 1158: 1154: 1153: 1135: 1131: 1130: 1112: 1108: 1107: 1089: 1085: 1084: 1066: 1062: 1061: 1043: 1039: 1038: 1018: 1014: 1013: 1010:greens, cooked 1001: 999: 995: 870: 855: 852: 851: 849: 831: 828: 827: 825: 821: 814: 813: 812: 811: 810: 808: 804: 800: 796: 793: 785: 784: 782: 778: 774: 770: 768:caesium oxalate 764: 750: 746: 742: 738: 732: 728: 726: 721: 717: 713: 709: 706: 702: 698: 694: 692:caesium oxalate 689: 683: 672: 661: 658: 657: 655: 651: 645: 642: 641: 639: 635: 632: 628: 624: 620: 614: 603: 601: 598: 585: 583: 580: 548: 545: 544: 542: 538: 535:hydrogenoxalate 523: 499: 495: 491: 487: 483: 474:), and several 472: 468: 464: 460: 442: 439: 438: 436: 432: 415: 408: 403: 387: 372: 366: 351:Hydrogenoxalate 337: 322: 319: 318: 316: 312: 309: 295: 292: 287: 286: 275: 272: 271: 268: 262: 261: 258: 252: 251: 240: 220: 207: 195: 172: 163: 143: 120: 111: 98: 87: 74: 60: 59: 48: 33: 30: 17: 12: 11: 5: 5276: 5274: 5266: 5265: 5260: 5258:Anticoagulants 5255: 5245: 5244: 5238: 5237: 5232: 5231: 5228: 5225: 5222: 5218: 5214: 5210: 5206: 5202: 5198: 5194: 5190: 5186: 5182: 5178: 5174: 5170: 5166: 5162: 5158: 5154: 5150: 5146: 5142: 5139: 5135: 5131: 5127: 5123: 5105: 5087: 5084: 5080: 5076: 5072: 5068: 5064: 5060: 5056: 5052: 5048: 5044: 5043: 5039: 5035: 5031: 5027: 5023: 5019: 5015: 5011: 5007: 5003: 4999: 4995: 4991: 4987: 4983: 4979: 4975: 4971: 4967: 4963: 4959: 4955: 4951: 4947: 4943: 4939: 4935: 4931: 4927: 4923: 4919: 4915: 4911: 4907: 4903: 4899: 4895: 4891: 4887: 4883: 4879: 4875: 4871: 4867: 4863: 4859: 4855: 4851: 4847: 4843: 4839: 4835: 4831: 4827: 4823: 4819: 4815: 4811: 4807: 4803: 4799: 4795: 4791: 4787: 4783: 4761: 4757: 4756: 4753: 4750: 4749: 4746: 4743: 4740: 4737: 4734: 4731: 4728: 4725: 4722: 4719: 4716: 4713: 4710: 4707: 4704: 4701: 4698: 4695: 4691: 4690: 4687: 4684: 4681: 4678: 4664: 4661: 4658: 4655: 4650: 4647: 4644: 4641: 4638: 4635: 4632: 4610: 4607: 4593: 4574: 4573: 4570: 4567: 4564: 4561: 4547: 4543: 4539: 4535: 4531: 4527: 4513: 4495: 4492: 4489: 4486: 4483: 4480: 4476: 4472: 4468: 4464: 4461: 4439: 4437: 4423: 4419: 4415: 4411: 4406: 4405: 4402: 4399: 4396: 4393: 4390: 4386: 4382: 4378: 4374: 4370: 4365: 4351: 4346: 4332: 4319: 4304: 4300: 4296: 4292: 4275: 4261: 4247: 4244: 4241: 4238: 4236: 4222: 4190: 4189: 4186: 4181: 4177: 4173: 4169: 4162: 4158: 4155: 4152: 4138: 4106: 4105: 4102: 4099: 4096: 4092: 4085: 4081: 4077: 4073: 4069: 4065: 4061: 4057: 4053: 4039: 4020: 4019: 4016: 4014: 4012: 4010: 4005: 4001: 3997: 3990: 3989: 3986: 3985: 3978: 3976: 3975: 3968: 3961: 3953: 3944: 3943: 3940: 3939: 3938: 3937: 3934: 3923: 3917: 3911: 3910: 3907: 3906: 3904: 3903: 3898: 3893: 3887: 3885: 3879: 3878: 3876: 3875: 3870: 3865: 3855: 3850: 3845: 3840: 3839: 3838: 3833: 3825: 3824: 3823: 3818: 3813: 3808: 3793: 3791: 3780: 3779: 3776: 3775: 3773: 3772: 3767: 3762: 3761: 3760: 3750: 3745: 3740: 3735: 3729: 3727: 3723: 3722: 3720: 3719: 3714: 3709: 3704: 3699: 3694: 3685: 3684: 3683: 3678: 3673: 3658: 3656: 3650: 3649: 3646: 3645: 3643: 3642: 3637: 3632: 3627: 3622: 3617: 3611: 3609: 3602: 3601: 3599: 3598: 3597: 3596: 3591: 3586: 3576: 3575: 3574: 3569: 3559: 3558: 3557: 3552: 3547: 3542: 3537: 3532: 3527: 3522: 3511: 3509: 3488: 3479: 3478: 3476: 3475: 3469: 3464: 3459: 3450: 3445: 3440: 3435: 3430: 3425: 3415: 3413: 3386: 3384:Anticoagulants 3380: 3379: 3376: 3375: 3373: 3372: 3367: 3362: 3356: 3354: 3350: 3349: 3347: 3346: 3341: 3336: 3330: 3328: 3322: 3321: 3319: 3318: 3317: 3316: 3311: 3301: 3300: 3299: 3294: 3289: 3273: 3271: 3265: 3264: 3262: 3261: 3256: 3251: 3246: 3241: 3235: 3233: 3231:COX inhibitors 3227: 3226: 3224: 3223: 3218: 3213: 3208: 3202: 3200: 3189: 3188: 3186: 3185: 3184: 3183: 3178: 3173: 3158: 3157: 3156: 3151: 3146: 3135: 3133: 3126: 3121: 3120: 3118: 3117: 3112: 3107: 3102: 3097: 3092: 3086: 3084: 3075: 3069: 3068: 3056:anticoagulants 3046: 3044: 3043: 3036: 3029: 3021: 3015: 3014: 3008: 3000: 2999:External links 2997: 2996: 2995: 2969:(4): 330–335. 2958: 2923: 2905: 2894: 2891: 2889: 2888: 2847: 2806: 2787:(5): 363–368. 2771: 2722: 2715: 2697: 2690: 2657: 2622: 2595: 2562: 2553: 2544: 2540: 2536: 2532: 2528: 2524: 2519:molecules: An 2516: 2512: 2503: 2476: 2449: 2409: 2400: 2379:(6): 783–788. 2359: 2340:(4): 938–939. 2317: 2298:(3): 417–418. 2279: 2272: 2244: 2216: 2201: 2199: 2196: 2185:Main article: 2182: 2179: 2150:kidney disease 2131: 2128: 2115: 2112: 2108:nephrotoxicity 2045:Main article: 2042: 2039: 1987:Main article: 1984: 1981: 1978: 1977: 1974: 1962: 1955: 1954: 1951: 1950:1 large stalk 1948: 1941: 1940: 1937: 1925: 1918: 1917: 1914: 1911: 1904: 1903: 1900: 1888: 1882: 1881: 1878: 1866: 1859: 1858: 1855: 1843: 1841:Concord grapes 1837: 1836: 1833: 1821: 1814: 1813: 1810: 1798: 1791: 1790: 1787: 1781: 1774: 1773: 1770: 1758: 1751: 1750: 1747: 1744: 1737: 1736: 1733: 1721: 1714: 1713: 1710: 1706: 1703:Milk chocolate 1699: 1698: 1695: 1692: 1685: 1684: 1681: 1669: 1662: 1661: 1658: 1655: 1648: 1647: 1644: 1641: 1634: 1633: 1630: 1618: 1611: 1610: 1607: 1604: 1597: 1596: 1593: 1581: 1575: 1574: 1571: 1559: 1552: 1551: 1548: 1537: 1530: 1529: 1526: 1500: 1499:, halves, raw 1493: 1492: 1489: 1477: 1474:Collard greens 1470: 1469: 1466: 1454: 1447: 1446: 1443: 1440: 1439:, unsweetened 1433: 1432: 1429: 1417: 1410: 1409: 1406: 1377: 1370: 1369: 1366: 1354: 1347: 1346: 1343: 1331: 1324: 1323: 1320: 1317: 1310: 1309: 1306: 1294: 1287: 1286: 1283: 1271: 1264: 1263: 1260: 1257: 1250: 1249: 1246: 1243: 1236: 1235: 1232: 1220: 1213: 1212: 1209: 1197: 1190: 1189: 1186: 1174: 1167: 1166: 1163: 1151: 1144: 1143: 1140: 1128: 1121: 1120: 1117: 1105: 1098: 1097: 1094: 1082: 1075: 1074: 1071: 1059: 1052: 1051: 1048: 1036: 1029: 1028: 1025: 1011: 1004: 1003: 996: 992: 956:fishtail palms 903:, and several 869: 866: 846:π interactions 794: 787: 786: 765: 758: 757: 756: 755: 754: 724: 687: 681: 671: 668: 612: 596: 578: 522: 519: 503:conjugate base 457:sodium oxalate 455:, for example 413: 410: 409: 404: 400:standard state 397: 394: 393: 388: 382: 379: 378: 374: 373: 370: 367: 362: 359: 358: 354: 353: 348: 346:Conjugate acid 342: 341: 335: 329: 328: 310: 305: 302: 301: 297: 296: 294: 293: 290: 282: 281: 280: 277: 276: 274: 273: 269: 266: 265: 263: 259: 256: 255: 247: 246: 245: 242: 241: 239: 238: 230: 228: 222: 221: 219: 218: 210: 208: 200: 197: 196: 194: 193: 185: 183: 177: 176: 173: 168: 165: 164: 162: 161: 153: 151: 145: 144: 142: 141: 133: 131: 125: 124: 121: 116: 113: 112: 110: 109: 101: 99: 92: 89: 88: 86: 85: 77: 75: 70: 67: 66: 62: 61: 57: 56: 50: 49: 46: 40: 39: 35: 34: 31: 15: 13: 10: 9: 6: 4: 3: 2: 5275: 5264: 5261: 5259: 5256: 5254: 5251: 5250: 5248: 5229: 5226: 5223: 5221: 5203: 5201: 5183: 5181: 5163: 5161: 5143: 5140: 5138: 5124: 5121: 5106: 5103: 5088: 5085: 5083: 5069: 5067: 5049: 5046: 5045: 5042: 5024: 5022: 5004: 5002: 4984: 4982: 4964: 4962: 4944: 4942: 4924: 4922: 4904: 4902: 4884: 4882: 4864: 4862: 4844: 4842: 4824: 4822: 4804: 4802: 4784: 4781: 4762: 4759: 4758: 4751: 4747: 4744: 4741: 4738: 4735: 4732: 4729: 4726: 4723: 4720: 4717: 4714: 4711: 4708: 4705: 4702: 4699: 4696: 4693: 4692: 4688: 4685: 4682: 4679: 4676: 4665: 4662: 4659: 4656: 4654: 4651: 4648: 4645: 4642: 4639: 4636: 4633: 4630: 4611: 4608: 4605: 4594: 4591: 4576: 4575: 4571: 4568: 4565: 4562: 4559: 4548: 4546: 4528: 4525: 4514: 4511: 4496: 4493: 4490: 4487: 4484: 4481: 4479: 4465: 4462: 4459: 4440: 4438: 4435: 4424: 4422: 4408: 4407: 4403: 4400: 4397: 4394: 4391: 4389: 4371: 4369: 4366: 4363: 4352: 4350: 4347: 4344: 4333: 4331: 4328: 4325: 4322: 4315: 4311: 4307: 4287: 4276: 4273: 4262: 4259: 4248: 4245: 4242: 4239: 4237: 4234: 4223: 4220: 4207: 4192: 4191: 4187: 4185: 4182: 4180: 4174: 4172: 4165: 4159: 4156: 4153: 4150: 4139: 4136: 4123: 4108: 4107: 4103: 4100: 4097: 4095: 4088: 4070: 4068: 4062: 4060: 4054: 4051: 4040: 4037: 4022: 4021: 4017: 4011: 4009: 3994: 3993: 3987: 3982: 3974: 3969: 3967: 3962: 3960: 3955: 3954: 3951: 3935: 3933: 3930: 3929: 3927: 3924: 3921: 3918: 3916: 3913: 3912: 3908: 3902: 3899: 3897: 3894: 3892: 3889: 3888: 3886: 3884: 3883:Non-medicinal 3880: 3874: 3871: 3869: 3866: 3864: 3860: 3856: 3854: 3853:Streptokinase 3851: 3849: 3846: 3844: 3841: 3837: 3834: 3832: 3829: 3828: 3826: 3822: 3819: 3817: 3814: 3812: 3809: 3807: 3804: 3803: 3802: 3798: 3795: 3794: 3792: 3790: 3789:fibrinolytics 3785: 3781: 3771: 3768: 3766: 3763: 3759: 3756: 3755: 3754: 3751: 3749: 3746: 3744: 3741: 3739: 3736: 3734: 3731: 3730: 3728: 3724: 3718: 3715: 3713: 3710: 3708: 3705: 3703: 3700: 3698: 3695: 3693: 3689: 3686: 3682: 3679: 3677: 3674: 3672: 3669: 3668: 3667: 3663: 3660: 3659: 3657: 3655: 3651: 3641: 3638: 3636: 3633: 3631: 3628: 3626: 3623: 3621: 3618: 3616: 3613: 3612: 3610: 3607: 3603: 3595: 3592: 3590: 3587: 3585: 3582: 3581: 3580: 3577: 3573: 3570: 3568: 3565: 3564: 3563: 3560: 3556: 3553: 3551: 3548: 3546: 3543: 3541: 3538: 3536: 3533: 3531: 3528: 3526: 3523: 3521: 3518: 3517: 3516: 3513: 3512: 3510: 3507: 3501: 3496: 3492: 3489: 3484: 3480: 3474: 3470: 3468: 3465: 3463: 3460: 3458: 3454: 3451: 3449: 3446: 3444: 3443:Phenprocoumon 3441: 3439: 3436: 3434: 3431: 3429: 3428:Coumatetralyl 3426: 3424: 3423:Acenocoumarol 3420: 3417: 3416: 3414: 3411: 3407: 3403: 3399: 3394: 3390: 3387: 3385: 3381: 3371: 3368: 3366: 3363: 3361: 3358: 3357: 3355: 3351: 3345: 3342: 3340: 3337: 3335: 3332: 3331: 3329: 3327: 3323: 3315: 3312: 3310: 3307: 3306: 3305: 3302: 3298: 3295: 3293: 3290: 3287: 3283: 3280: 3279: 3278: 3275: 3274: 3272: 3270: 3266: 3260: 3257: 3255: 3252: 3250: 3247: 3245: 3242: 3240: 3237: 3236: 3234: 3232: 3228: 3222: 3219: 3217: 3214: 3212: 3209: 3207: 3204: 3203: 3201: 3198: 3194: 3190: 3182: 3179: 3177: 3174: 3172: 3169: 3168: 3166: 3162: 3159: 3155: 3152: 3150: 3147: 3145: 3142: 3141: 3140: 3137: 3136: 3134: 3132: 3129: 3122: 3116: 3113: 3111: 3108: 3106: 3103: 3101: 3098: 3096: 3093: 3091: 3088: 3087: 3085: 3083: 3079: 3076: 3074: 3070: 3065: 3061: 3057: 3053: 3052:thrombolytics 3049: 3042: 3037: 3035: 3030: 3028: 3023: 3022: 3019: 3012: 3009: 3006: 3003: 3002: 2998: 2992: 2988: 2984: 2980: 2976: 2972: 2968: 2964: 2959: 2955: 2951: 2946: 2941: 2937: 2933: 2929: 2924: 2913: 2909: 2904: 2897: 2896: 2892: 2884: 2880: 2875: 2870: 2866: 2862: 2858: 2851: 2848: 2843: 2839: 2834: 2829: 2825: 2821: 2817: 2810: 2807: 2802: 2798: 2794: 2790: 2786: 2782: 2775: 2772: 2767: 2763: 2758: 2753: 2749: 2745: 2741: 2737: 2733: 2726: 2723: 2718: 2716:0-7216-2439-1 2712: 2708: 2701: 2698: 2693: 2691:9780024180100 2687: 2683: 2678: 2677: 2671: 2667: 2661: 2658: 2653: 2649: 2645: 2641: 2637: 2633: 2626: 2623: 2618: 2614: 2610: 2606: 2599: 2596: 2591: 2587: 2583: 2579: 2575: 2571: 2522: 2507: 2504: 2499: 2495: 2491: 2487: 2480: 2477: 2472: 2468: 2464: 2460: 2453: 2450: 2445: 2441: 2437: 2433: 2429: 2425: 2418: 2416: 2414: 2410: 2404: 2401: 2395: 2390: 2386: 2382: 2378: 2374: 2370: 2363: 2360: 2355: 2351: 2347: 2343: 2339: 2335: 2328: 2321: 2318: 2313: 2309: 2305: 2301: 2297: 2293: 2286: 2284: 2280: 2275: 2273:3-527-30673-0 2269: 2265: 2261: 2257: 2256: 2248: 2245: 2241: 2230: 2229:www.ebi.ac.uk 2226: 2220: 2217: 2212: 2206: 2203: 2197: 2195: 2193: 2188: 2180: 2178: 2176: 2172: 2171: 2166: 2161: 2160: 2155: 2151: 2147: 2143: 2139: 2138: 2129: 2127: 2125: 2124:hyperoxaluria 2121: 2120:hyperoxalemia 2113: 2111: 2109: 2105: 2101: 2077: 2062: 2058: 2054: 2048: 2040: 2038: 2036: 2035: 2031: 2027: 2022: 2020: 2016: 2012: 2004: 2000: 1995: 1990: 1982: 1975: 1963: 1960: 1957: 1956: 1952: 1949: 1946: 1943: 1942: 1938: 1926: 1923: 1920: 1919: 1915: 1912: 1909: 1906: 1905: 1901: 1889: 1887: 1884: 1883: 1879: 1867: 1864: 1861: 1860: 1856: 1844: 1842: 1839: 1838: 1834: 1822: 1819: 1816: 1815: 1811: 1799: 1796: 1793: 1792: 1788: 1786: 1782: 1779: 1776: 1775: 1771: 1759: 1756: 1753: 1752: 1748: 1745: 1742: 1739: 1738: 1734: 1722: 1720:, black, raw 1719: 1716: 1715: 1711: 1707: 1704: 1701: 1700: 1696: 1693: 1690: 1687: 1686: 1682: 1670: 1667: 1664: 1663: 1659: 1656: 1653: 1650: 1649: 1645: 1642: 1639: 1636: 1635: 1631: 1619: 1616: 1613: 1612: 1608: 1605: 1602: 1599: 1598: 1594: 1582: 1580: 1577: 1576: 1572: 1560: 1557: 1554: 1553: 1549: 1546: 1542: 1538: 1535: 1532: 1531: 1527: 1501: 1498: 1495: 1494: 1490: 1478: 1475: 1472: 1471: 1467: 1455: 1452: 1449: 1448: 1444: 1441: 1438: 1435: 1434: 1430: 1418: 1415: 1412: 1411: 1407: 1404: 1378: 1375: 1372: 1371: 1367: 1355: 1352: 1349: 1348: 1344: 1332: 1329: 1326: 1325: 1321: 1318: 1315: 1312: 1311: 1307: 1295: 1292: 1289: 1288: 1284: 1272: 1269: 1266: 1265: 1261: 1258: 1255: 1252: 1251: 1247: 1244: 1241: 1238: 1237: 1233: 1221: 1218: 1215: 1214: 1210: 1198: 1195: 1192: 1191: 1187: 1175: 1172: 1169: 1168: 1164: 1152: 1149: 1146: 1145: 1141: 1129: 1126: 1123: 1122: 1118: 1106: 1103: 1100: 1099: 1095: 1083: 1080: 1077: 1076: 1072: 1060: 1057: 1054: 1053: 1049: 1037: 1034: 1031: 1030: 1026: 1024: 1012: 1009: 1006: 1005: 997: 993: 990: 989: 983: 981: 977: 976: 971: 967: 963: 962: 957: 953: 949: 945: 941: 937: 933: 929: 925: 921: 917: 913: 908: 907: 902: 898: 894: 890: 886: 881: 879: 875: 867: 865: 863: 847: 844:with minimal 843: 839: 819: 791: 769: 762: 753: 737: 693: 685: 677: 669: 667: 618: 611: 599: 595: 581: 577: 572: 568: 564: 560: 556: 536: 532: 528: 520: 518: 516: 512: 509:. At neutral 508: 504: 481: 477: 458: 454: 450: 431: 427: 423: 419: 407: 401: 395: 392: 389: 386: 385:isoelectronic 381: 380: 375: 368: 365: 361: 360: 355: 352: 349: 347: 344: 343: 336: 334: 331: 330: 311: 308: 304: 303: 298: 289: 285: 278: 264: 254: 250: 243: 236: 232: 231: 229: 227: 224: 223: 216: 212: 211: 209: 203: 199: 198: 191: 187: 186: 184: 182: 179: 178: 174: 171: 167: 166: 159: 155: 154: 152: 150: 147: 146: 139: 135: 134: 132: 130: 127: 126: 122: 119: 115: 114: 107: 103: 102: 100: 96: 91: 90: 83: 79: 78: 76: 73: 69: 68: 63: 55: 51: 45: 41: 36: 28: 23: 3980: 3900: 3873:Fibrinolysin 3843:Anistreplase 3821:Desmoteplase 3816:Tenecteplase 3717:Ximelagatran 3567:Fondaparinux 3506:antithrombin 3462:Diphenadione 3339:Dipyridamole 3282:Dipyridamole 3221:Treprostinil 3216:Prostacyclin 3095:Eptifibatide 2966: 2962: 2935: 2931: 2915:. Retrieved 2911: 2902: 2864: 2860: 2850: 2823: 2819: 2809: 2784: 2780: 2774: 2739: 2735: 2725: 2706: 2700: 2675: 2660: 2635: 2631: 2625: 2608: 2604: 2598: 2573: 2569: 2520: 2506: 2485: 2479: 2458: 2452: 2427: 2423: 2403: 2376: 2372: 2362: 2337: 2333: 2320: 2295: 2291: 2254: 2247: 2239: 2232:. Retrieved 2228: 2219: 2205: 2190: 2168: 2157: 2135: 2133: 2119: 2117: 2056: 2050: 2032: 2023: 2011:kidney stone 2008: 1999:kidney stone 1989:Kidney stone 1818:Blackberries 1666:Strawberries 1579:Gooseberries 1328:Sweet potato 973: 959: 916:black pepper 904: 882: 871: 815: 673: 609: 593: 575: 563:acid oxalate 524: 422:ethanedioate 421: 417: 416: 291:C(=O)(C(=O)) 65:Identifiers 58:Ethanedioate 4368:Katsarosite 4314:humboldtine 3922:from market 3743:Defibrotide 3671:Bivalirudin 3640:Rivaroxaban 3579:Heparinoids 3572:Idraparinux 3473:Tioclomarol 3467:Phenindione 3457:Clorindione 3360:Cloricromen 3154:Ticlopidine 3144:Clopidogrel 3005:Oxalate.org 2938:(10): 924. 2912:chm.uri.edu 2165:proteinuria 2142:wood sorrel 2100:oxaliplatin 2098:. The drug 2034:Aspergillus 2019:risk factor 1924:, red, raw 1922:Raspberries 1886:Redcurrants 1863:Blueberries 1755:Green beans 1718:Raspberries 1657:6–8 medium 1556:Cereal germ 878:saccharides 842:single bond 507:oxalic acid 501:). It is a 364:Point group 300:Properties 138:CHEBI:30623 5247:Categories 3848:Monteplase 3765:Ramatroban 3748:Nafamostat 3733:Abelacimab 3712:Melagatran 3697:Dabigatran 3692:Argatroban 3635:Otamixaban 3620:Betrixaban 3608:("xabans") 3594:Sulodexide 3584:Danaparoid 3555:Tinzaparin 3545:Parnaparin 3540:Nadroparin 3535:Enoxaparin 3530:Dalteparin 3525:Certoparin 3485:inhibitors 3433:Dicoumarol 3334:Cilostazol 3314:Terutroban 3292:Picotamide 3181:Ticagrelor 3165:nucleoside 3161:Nucleotide 3131:inhibitors 3110:Sibrafiban 2523:Study of B 2198:References 2181:Congenital 2003:weddellite 1785:tablespoon 1558:, toasted 1196:, pickled 991:Food item 924:poppy seed 557:with this 357:Structure 333:Molar mass 235:PQ7QG47K6T 149:ChemSpider 93:3D model ( 72:CAS Number 44:IUPAC name 3932:Phase III 3920:Withdrawn 3836:Urokinase 3831:Saruplase 3811:Reteplase 3806:Alteplase 3753:Protein C 3707:Inogatran 3702:Efegatran 3688:Univalent 3681:Lepirudin 3676:Desirudin 3625:Darexaban 3550:Reviparin 3520:Bemiparin 3483:Factor Xa 3419:Coumarins 3396:(inhibit 3370:Vorapaxar 3344:Triflusal 3309:Terbogrel 3297:Terbogrel 3286:+ aspirin 3259:Triflusal 3254:Indobufen 3244:Aloxiprin 3206:Beraprost 3176:Elinogrel 3171:Cangrelor 3149:Prasugrel 3115:Tirofiban 3105:Roxifiban 3100:Orbofiban 3090:Abciximab 2983:2000-0669 2954:2073-4352 2576:: 20–29. 2521:ab initio 2234:2 January 2211:"Oxalate" 2175:gut flora 2146:black tea 2084:[Fe(C 1959:Cranberry 1947:, cooked 1913:2 medium 1757:, cooked 1746:1 medium 1694:2 stalks 1654:, cooked 1643:1 medium 1617:, cooked 1606:1 medium 1476:, cooked 1437:Chocolate 1353:, cooked 1330:, cooked 1319:8–9 pods 1316:, cooked 1291:Dandelion 1173:, frozen 1150:, canned 1104:, cooked 1081:, cooked 944:chocolate 912:carambola 893:buckwheat 874:oxidation 676:dihedrals 670:Structure 428:with the 5253:Oxalates 3662:Bivalent 3630:Edoxaban 3615:Apixaban 3448:Warfarin 3365:Ditazole 3211:Iloprost 3167:analogs 2991:96834193 2932:Crystals 2883:23536130 2842:25830441 2801:16047945 2766:30566003 2672:(1976). 2590:98744097 2444:12611516 2152:or even 2130:Acquired 2104:platinum 1945:Broccoli 1908:Apricots 1539:1 level 1451:Parsnips 1033:Purslane 1008:Beetroot 980:infusion 928:amaranth 838:C−C bond 684:symmetry 478:such as 424:) is an 383:Related 123:1905970 82:338-70-5 20:Oxalate 4755:  3981:oxalate 3901:Oxalate 3891:Citrate 3868:Brinase 3666:Hirudin 3495:Heparin 3471:Other: 2917:10 June 2899:Euler. 2757:6459305 2640:Bibcode 2381:Bibcode 2342:Bibcode 2300:Bibcode 2173:in the 2028:of the 1968:⁄ 1931:⁄ 1894:⁄ 1872:⁄ 1849:⁄ 1827:⁄ 1809:medium 1804:⁄ 1764:⁄ 1727:⁄ 1675:⁄ 1624:⁄ 1615:Carrots 1587:⁄ 1565:⁄ 1520:⁄ 1506:⁄ 1483:⁄ 1460:⁄ 1423:⁄ 1397:⁄ 1383:⁄ 1374:Peanuts 1360:⁄ 1337:⁄ 1300:⁄ 1277:⁄ 1226:⁄ 1203:⁄ 1180:⁄ 1171:Spinach 1157:⁄ 1148:Rhubarb 1134:⁄ 1111:⁄ 1088:⁄ 1079:Spinach 1065:⁄ 1056:Rhubarb 1042:⁄ 1017:⁄ 1000:content 998:Oxalate 994:Serving 972:plant ( 964:), and 952:berries 950:, most 946:, most 920:parsley 897:fat hen 889:rhubarb 885:spinach 527:protons 449:dianion 447:. This 418:Oxalate 327: 202:PubChem 47:Oxalate 3915:WHO-EM 3863:Ancrod 3857:Other 3504:(bind 3497:group/ 2989:  2981:  2952:  2881:  2840:  2799:  2764:  2754:  2713:  2688:  2588:  2547:, and 2442:  2270:  2114:Excess 1961:juice 1910:, raw 1865:, raw 1820:, raw 1797:, raw 1778:Chives 1741:Orange 1691:, raw 1689:Celery 1668:, raw 1601:Potato 1547:water 1497:Pecans 1414:Turnip 1376:, raw 1270:, dry 1256:, raw 1254:Endive 1242:, raw 1240:Almond 906:Oxalis 901:sorrel 891:, and 650:, and 569:. The 537:anion 476:esters 338:88.018 284:SMILES 190:C00209 38:Names 4467:Nb(HC 3801:r-tPA 3726:Other 3353:Other 2987:S2CID 2586:S2CID 2330:(PDF) 2154:death 2030:genus 2026:fungi 2024:Some 1795:Leeks 1638:Apple 1545:fl oz 1543:in 7 1511:cup ( 1442:1 oz 1388:cup ( 1268:Cocoa 1245:1 oz 1125:Chard 1002:(mg) 966:beans 940:cocoa 936:beets 932:chard 559:anion 453:salts 426:anion 249:InChI 215:71081 175:2207 158:64235 129:ChEBI 95:JSmol 5126:Pu(C 5109:Np(C 5071:Th(C 4128:NaHC 3896:EDTA 3827:UPA 3770:REG1 3197:PGI2 3058:and 2979:ISSN 2950:ISSN 2919:2021 2879:PMID 2838:PMID 2797:PMID 2762:PMID 2711:ISBN 2686:ISBN 2440:PMID 2268:ISBN 2236:2019 2017:, a 1936:cup 1899:cup 1877:cup 1854:cup 1832:cup 1769:cup 1732:cup 1705:bar 1680:cup 1629:cup 1592:cup 1570:cup 1525:oz) 1488:cup 1465:cup 1431:110 1428:cup 1408:113 1368:125 1365:cup 1351:Kale 1345:141 1342:cup 1322:146 1314:Okra 1308:246 1305:cup 1285:254 1282:cup 1262:273 1248:296 1234:476 1231:cup 1217:Poke 1211:500 1208:cup 1194:Beet 1188:600 1185:cup 1165:600 1162:cup 1142:660 1139:cup 1119:675 1116:cup 1102:Beet 1096:750 1093:cup 1073:860 1070:cup 1050:910 1047:cup 1027:916 948:nuts 816:The 602:5.25 584:5.37 555:salt 553:. A 226:UNII 181:KEGG 5230:No 5227:Md 5224:Fm 5141:Am 5086:Pa 5047:** 4748:Og 4745:Ts 4742:Lv 4739:Mc 4736:Fl 4733:Nh 4730:Cn 4727:Rg 4724:Ds 4721:Mt 4718:Hs 4715:Bh 4712:Sg 4709:Db 4706:Rf 4703:Lr 4700:** 4697:Ra 4694:Fr 4689:Rn 4686:At 4683:Po 4680:Bi 4668:PbC 4663:Tl 4660:Hg 4657:Au 4653:-Pt 4649:Ir 4646:Os 4643:Re 4637:Ta 4634:Hf 4597:BaC 4572:Xe 4566:Te 4563:Sb 4551:SnC 4517:CdC 4494:Pd 4491:Rh 4488:Ru 4485:Tc 4482:Mo 4463:Zr 4427:SrC 4404:Kr 4401:Br 4398:Se 4395:As 4392:Ge 4355:CuC 4349:-Ni 4336:CoC 4324:+Na 4318:+NH 4310:+Fe 4279:FeC 4265:MnC 4251:CrC 4243:Ti 4240:Sc 4226:CaC 4212:KHC 4188:Ar 4184:+Cl 4176:+SO 4168:+PO 4161:+PO 4157:Si 4154:Al 4142:MgC 4104:Ne 4091:+NO 4072:(NH 4064:+CO 4056:+BO 4043:BeC 4018:He 3983:ion 3402:VII 3064:B01 3062:) ( 2971:doi 2940:doi 2869:doi 2828:doi 2824:372 2789:doi 2785:201 2752:PMC 2744:doi 2740:316 2682:737 2648:doi 2636:104 2613:doi 2609:209 2578:doi 2568:". 2539:, N 2531:, B 2494:doi 2467:doi 2432:doi 2389:doi 2350:doi 2308:doi 2260:doi 1939:10 1916:10 1902:11 1880:11 1857:13 1835:13 1812:15 1789:19 1772:23 1749:24 1735:33 1712:34 1697:34 1683:35 1660:37 1646:41 1632:45 1609:64 1595:66 1573:67 1550:72 1541:tsp 1534:Tea 1528:74 1491:74 1468:81 1445:91 1023:cup 970:tea 914:), 876:of 513:in 505:of 484:(CH 205:CID 5249:: 5209:(C 5205:Es 5189:(C 5185:Cf 5169:(C 5165:Bk 5149:(C 5145:Cm 5091:UO 5055:(C 5051:Ac 5030:(C 5026:Yb 5010:(C 5006:Tm 4990:(C 4986:Er 4970:(C 4966:Ho 4950:(C 4946:Dy 4930:(C 4926:Tb 4910:(C 4906:Gd 4890:(C 4886:Eu 4870:(C 4866:Sm 4850:(C 4846:Pm 4830:(C 4826:Nd 4810:(C 4806:Pr 4790:(C 4786:Ce 4769:(C 4765:La 4760:* 4640:W 4618:(C 4614:Lu 4609:* 4579:Cs 4569:I 4534:(C 4530:In 4499:Ag 4447:(C 4410:Rb 4377:(C 4373:Ga 4330:+K 4327:+K 4295:(C 4291:Fe 4246:V 4111:Na 4101:F 4098:O 4025:Li 3996:(H 3928:: 3861:: 3799:: 3690:: 3664:: 3455:: 3421:: 3408:, 3406:IX 3404:, 3400:, 3398:II 3127:12 3054:, 2985:. 2977:. 2967:14 2965:. 2948:. 2936:10 2934:. 2930:. 2910:. 2906:sp 2877:. 2865:83 2863:. 2859:. 2836:. 2822:. 2818:. 2795:. 2783:. 2760:. 2750:. 2738:. 2734:. 2684:. 2668:; 2646:. 2634:. 2607:. 2584:. 2572:. 2535:Cl 2492:. 2488:. 2465:. 2461:. 2438:. 2428:42 2426:. 2412:^ 2387:. 2377:17 2375:. 2371:. 2348:. 2338:37 2336:. 2332:. 2306:. 2296:89 2294:. 2282:^ 2266:. 2258:. 2238:. 2227:. 2126:. 2078:, 2065:MC 2057:ox 1976:6 1953:6 1783:1 1405:) 1403:oz 954:, 942:, 938:, 934:, 930:, 926:, 922:, 918:, 887:, 880:. 850:CO 829:2− 771:Cs 739:Rb 729:CO 725:2d 710:Cs 695:Cs 688:2h 682:2d 659:2− 636:HC 634:, 617:pH 608:(p 606:10 588:10 539:HC 511:pH 461:Na 440:2− 371:2h 320:2− 5219:3 5217:) 5215:4 5213:O 5211:2 5207:2 5199:3 5197:) 5195:4 5193:O 5191:2 5187:2 5179:3 5177:) 5175:4 5173:O 5171:2 5167:2 5159:3 5157:) 5155:4 5153:O 5151:2 5147:2 5136:2 5134:) 5132:4 5130:O 5128:2 5119:2 5117:) 5115:4 5113:O 5111:2 5101:4 5099:O 5097:2 5095:C 5093:2 5081:2 5079:) 5077:4 5075:O 5073:2 5065:3 5063:) 5061:4 5059:O 5057:2 5053:2 5040:3 5038:) 5036:4 5034:O 5032:2 5028:2 5020:3 5018:) 5016:4 5014:O 5012:2 5008:2 5000:3 4998:) 4996:4 4994:O 4992:2 4988:2 4980:3 4978:) 4976:4 4974:O 4972:2 4968:2 4960:3 4958:) 4956:4 4954:O 4952:2 4948:2 4940:3 4938:) 4936:4 4934:O 4932:2 4928:2 4920:3 4918:) 4916:4 4914:O 4912:2 4908:2 4900:3 4898:) 4896:4 4894:O 4892:2 4888:2 4880:3 4878:) 4876:4 4874:O 4872:2 4868:2 4860:3 4858:) 4856:4 4854:O 4852:2 4848:2 4840:3 4838:) 4836:4 4834:O 4832:2 4828:2 4820:3 4818:) 4816:4 4814:O 4812:2 4808:2 4800:3 4798:) 4796:4 4794:O 4792:2 4788:2 4779:3 4777:) 4775:4 4773:O 4771:2 4767:2 4674:4 4672:O 4670:2 4628:3 4626:) 4624:4 4622:O 4620:2 4616:2 4603:4 4601:O 4599:2 4589:4 4587:O 4585:2 4583:C 4581:2 4557:4 4555:O 4553:2 4544:3 4542:) 4540:4 4538:O 4536:2 4532:2 4523:4 4521:O 4519:2 4509:4 4507:O 4505:2 4503:C 4501:2 4477:5 4475:) 4473:4 4471:O 4469:2 4457:3 4455:) 4453:4 4451:O 4449:2 4445:2 4443:Y 4433:4 4431:O 4429:2 4420:4 4418:O 4416:2 4414:C 4412:2 4387:3 4385:) 4383:4 4381:O 4379:2 4375:2 4361:4 4359:O 4357:2 4342:4 4340:O 4338:2 4320:4 4305:3 4303:) 4301:4 4299:O 4297:2 4293:2 4285:4 4283:O 4281:2 4271:4 4269:O 4267:2 4257:4 4255:O 4253:2 4232:4 4230:O 4228:2 4218:4 4216:O 4214:2 4205:4 4203:O 4201:2 4199:C 4197:2 4195:K 4178:4 4170:3 4163:4 4148:4 4146:O 4144:2 4134:4 4132:O 4130:2 4121:4 4119:O 4117:2 4115:C 4113:2 4093:3 4086:4 4084:O 4082:2 4080:C 4078:2 4076:) 4074:4 4066:3 4058:3 4049:4 4047:O 4045:2 4035:4 4033:O 4031:2 4029:C 4027:2 4008:) 4006:4 4004:O 4002:2 4000:C 3998:2 3972:e 3965:t 3958:v 3786:/ 3508:) 3502:/ 3412:) 3410:X 3288:) 3284:( 3199:) 3195:( 3163:/ 3066:) 3050:( 3040:e 3033:t 3026:v 2993:. 2973:: 2956:. 2942:: 2921:. 2903:K 2901:" 2885:. 2871:: 2844:. 2830:: 2803:. 2791:: 2768:. 2746:: 2719:. 2694:. 2654:. 2650:: 2642:: 2619:. 2615:: 2592:. 2580:: 2574:2 2563:4 2558:O 2554:2 2549:C 2545:4 2543:O 2541:2 2537:4 2533:2 2529:4 2527:F 2525:2 2517:4 2515:X 2513:2 2500:. 2496:: 2473:. 2469:: 2446:. 2434:: 2397:. 2391:: 2383:: 2356:. 2352:: 2344:: 2314:. 2310:: 2302:: 2276:. 2262:: 2213:. 2096:] 2094:3 2092:) 2090:4 2088:O 2086:2 2082:3 2080:K 2071:2 2069:O 2067:2 1970:2 1966:1 1933:2 1929:1 1896:2 1892:1 1874:2 1870:1 1851:2 1847:1 1829:2 1825:1 1806:2 1802:1 1766:2 1762:1 1729:2 1725:1 1677:2 1673:1 1626:2 1622:1 1589:2 1585:1 1567:4 1563:1 1522:4 1518:1 1515:+ 1513:1 1508:3 1504:1 1485:2 1481:1 1462:2 1458:1 1425:2 1421:1 1399:4 1395:3 1392:+ 1390:1 1385:3 1381:1 1362:2 1358:1 1339:2 1335:1 1302:2 1298:1 1279:3 1275:1 1228:2 1224:1 1205:2 1201:1 1182:2 1178:1 1159:2 1155:1 1136:2 1132:1 1113:2 1109:1 1090:2 1086:1 1067:2 1063:1 1044:2 1040:1 1019:2 1015:1 910:( 856:2 853:− 832:4 826:O 824:2 822:C 807:4 805:O 803:2 801:C 799:2 797:K 781:4 779:O 777:2 775:C 773:2 749:4 747:O 745:2 743:C 741:2 731:2 720:4 718:O 716:2 714:C 712:2 705:4 703:O 701:2 699:C 697:2 680:D 662:4 656:O 654:2 652:C 646:4 643:− 640:O 638:2 631:4 629:O 627:2 625:C 623:2 621:H 613:a 610:K 604:× 597:a 594:K 592:p 590:( 586:× 579:a 576:K 573:( 549:4 546:− 543:O 541:2 498:4 496:O 494:2 492:C 490:2 488:) 486:3 482:( 471:4 469:O 467:2 465:C 463:2 459:( 443:4 437:O 435:2 433:C 369:D 323:4 317:O 315:2 313:C 97:)

Index

two capital Cs connected to each other by a solid line and each connected to two separate Os by a solid line and a dashed line next to the solid line, the whole thing in brackets with a −2 to the top-right
IUPAC name
Systematic IUPAC name
CAS Number
338-70-5
JSmol
Interactive image
Beilstein Reference
ChEBI
CHEBI:30623
ChemSpider
64235
Gmelin Reference
KEGG
C00209
PubChem
71081
UNII
PQ7QG47K6T
InChI
SMILES
Chemical formula
Molar mass
Conjugate acid
Hydrogenoxalate
Point group
isoelectronic
Dinitrogen tetroxide
standard state
Infobox references

Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.