308:
285:
40:
892:
Plater MJ, Foreman MR, Skakle JM, Howie RA (April 2002). "Hydrothermal crystallisation of metal (II) orotates (M= nickel, cobalt, manganese or zinc). Effect of 2, 2-bipyridyl, 2, 2-dipyridyl amine, 1-methyl-3-(2-pyridyl) pyrazole, phenanthroline and 2,9-dimethyl-1,10-phenanthroline upon structure".
620:
converts into a polymeric trihydrate upon heating in water at 100 °C. Crystals of the trihydrate can be obtained by hydrothermal treatment of nickel(II) acetate and orotic acid. When the reactions are run with bidentate nitrogen ligands such as
656:, an X-linked inherited and the most common urea cycle disorder, excess carbamoyl phosphate is converted into orotic acid. This leads to an increased serum ammonia level, increased serum and urinary orotic acid levels and a decreased serum
660:
level. This also leads to an increased urinary orotic acid excretion, because the orotic acid is not being properly utilized and must be eliminated. The hyperammonemia depletes alpha-ketoglutarate leading to the inhibition of the
959:
1217:
78:
435:
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1322:
825:
Bach I, Kumberger O, Schmidbaur H (1990). "Orotate complexes. Synthesis and crystal structure of lithium orotate(—I) monohydrate and magnesium bis octahydrate".
692:. It is reasoned that the smoking causes the pyrimidine biosynthesis process in the mother to be altered thus causing the orotic acid concentration to increase.
60:
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987:
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Karatas F (October 2002). "An investigation of orotic acid levels in the breastmilk of smoking and non-smoking mothers".
1280:
1157:
Greenbaum SB (1954). "Potential
Metabolic Antagonists of Orotic Acid: 6-Uracilsulfonamide and 6-Uracil Methyl Sulfone".
557:
518:
224:
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264:
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Ashihara H, Stasolla C, Loukanina N, Thorpe TA (2000). "Purine and pyrimidine metabolism in cultured white spruce (
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Karipides AN, Thomas B (1986). "The structures of tetraaqua(uracil-6-carboxylate)zinc(II) monohydrate (
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Sartori HE (1986). "Lithium orotate in the treatment of alcoholism and related conditions".
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766:"Requirements for the mitochondrial import and localization of dihydroorotate dehydrogenase"
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990:(September 2014). "Inborn errors of pyrimidine metabolism: clinical update and therapy".
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924:-1,2,3,6-tetrahydro-2,6-dioxopyrimidine-4-carboxylato-N,O,O')-triaqua-nickel(ii))".
1406:
699:. The mutant yeasts which are resistant to 5-fluoroorotic acid require a supply of
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920:
Plater MJ, Foreman MR, Skakle JM, Howie RA (2002). "CCDC 189770 – Catena-((μ
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153:
572:, whereas purine synthesis happens by building the base directly on the sugar.
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1037:) cells: Metabolic fate of C-labeled precursors and activity of key enzymes".
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is that the pyrimidine ring is fully synthesized before being attached to the
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InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
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has a higher concentration of orotic acid than that of a non smoking
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Chemical compound synthesized in the body via a mitochondrial enzyme
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814:(5th ed.). Lippincott, Williams & Wilkins. p. 302.
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Rawls J, Knecht W, Diekert K, Lill R, Löffler M (April 2000).
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Adrio JL, Veiga M, Casqueiro J, López M, Fernández C (1993).
953:) and tetraaqua(uracil-6-carboxylato)nickel(II) monohydrate (
461:
269:
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dihydroorotate dehydrogenase, where it later combines with
470:
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A modified orotic acid (5-fluoroorotic acid) is toxic to
596:, for example, has been investigated for use in treating
476:
110:
1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
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Orotic acid is a precursor to a RNA base, uracil. The
442:
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Orotic aciduria is a cause of megaloblastic anaemia.
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495:. Historically, it was believed to be part of the
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637:and acidemia. It may be a symptom of an increased
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1117:The Journal of General and Applied Microbiology
887:
885:
127:
1323:Phosphoribosylaminoimidazolesuccinocarboxamide
513:The compound is synthesized in the body via a
1211:
616:are known. The pentahydrate nickel orotate
8:
1317:5′-Phosphoribosyl-4-carboxy-5-aminoimidazole
30:
1335:5-Formamidoimidazole-4-carboxamide ribotide
1485:
1437:
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1244:
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1113:auxotrophic mutants by enrichment methods"
564:(OMP). A distinguishing characteristic of
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1188:at the U.S. National Library of Medicine
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1159:Journal of the American Chemical Society
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625:present, other solids can be obtained.
506:, but it is now known that it is not a
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1066:European Journal of Clinical Nutrition
992:Journal of Inherited Metabolic Disease
927:Cambridge Crystallographic Data Centre
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29:
654:ornithine transcarbamylase deficiency
633:A buildup of orotic acid can lead to
552:is synthesized to orotic acid by the
69:
7:
1305:5′-Phosphoribosylformylglycinamidine
1051:10.1034/j.1399-3054.2000.108001025.x
1299:Phosphoribosyl-N-formylglycineamide
252:
143:
805:Harvey D, Ferrier D, eds. (2008).
25:
783:10.1046/j.1432-1327.2000.01213.x
770:European Journal of Biochemistry
457:
337:
331:
38:
424:Key:PXQPEWDEAKTCGB-UHFFFAOYSA-N
1575:Drugs not assigned an ATC code
743:Merriam-Webster.com Dictionary
592:, is able to bind to metals.
343:
325:
1:
986:Balasubramaniam S, Duley JA,
907:10.1016/S0020-1693(02)00728-4
1281:Phosphoribosyl pyrophosphate
868:10.1016/0741-8329(86)90018-2
558:phosphoribosyl pyrophosphate
525:. It is sometimes used as a
523:pyrimidine synthesis pathway
519:dihydroorotate dehydrogenase
1293:Glycineamide ribonucleotide
521:or a cytoplasmic enzyme of
1601:
1468:Orotidine 5'-monophosphate
562:orotidine-5'-monophosphate
315:Chemical and physical data
1311:5-Aminoimidazole ribotide
1004:10.1007/s10545-014-9742-3
973:10.1107/S0108270186090856
432:
407:
399:O=C(O)\C1=C\C(=O)NC(=O)N1
387:
98:
37:
18:Pyrimidinecarboxylic acid
1384:Xanthosine monophosphate
1190:Medical Subject Headings
841:10.1002/cber.19901231207
663:tricarboxylic acid cycle
71:International Drug Names
55:uracil-6-carboxylic acid
1546:β-Ureidoisobutyric acid
1448:Carbamoyl aspartic acid
1230:metabolic intermediates
1078:10.1038/sj.ejcn.1601420
895:Inorganica Chimica Acta
718:Pyrimidine biosynthesis
499:complex and was called
1536:3-Aminoisobutyric acid
1513:3-Ureidopropionic acid
1458:4,5-Dihydroorotic acid
667:adenosine triphosphate
1473:Uridine monophosphate
1039:Physiologia Plantarum
537:), most commonly for
618:coordination complex
566:pyrimidine synthesis
1453:Carbamoyl phosphate
1329:AICA ribonucleotide
1287:Phosphoribosylamine
1171:10.1021/ja01652a056
1130:10.2323/jgam.39.303
658:blood urea nitrogen
647:urea cycle disorder
600:, and complexes of
533:(to increase their
531:dietary supplements
34:
1275:Ribose 5-phosphate
828:Chemische Berichte
669:(ATP) production.
643:metabolic disorder
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1402:5-Hydroxyisourate
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1165:(23): 6052–6054.
1111:Phaffia rhodozyma
967:(12): 1705–1707.
835:(12): 2267–2271.
746:. Merriam-Webster
713:Magnesium orotate
665:(TCA) decreasing
580:Orotic acid is a
450:
449:
378:Interactive image
265:CompTox Dashboard
16:(Redirected from
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1580:Pyrimidinediones
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594:Lithium orotate
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560:(PRPP) to form
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539:lithium orotate
535:bioavailability
527:mineral carrier
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493:carboxylic acid
489:pyrimidinedione
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738:"Orotic acid"
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1407:Hypoxanthine
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748:. Retrieved
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676:Biochemistry
671:
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645:, such as a
632:
579:
570:ribose sugar
548:
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1585:Enoic acids
1463:Orotic acid
1186:Orotic+Acid
682:breast milk
453:Orotic acid
361: g·mol
304:100.000.563
94:Identifiers
52:Other names
32:Orotic acid
1569:Categories
1482:catabolism
1433:metabolism
1431:pyrimidine
1395:catabolism
1240:metabolism
1227:Nucleotide
750:2023-02-07
724:References
623:bipyridine
598:alcoholism
366:3D model (
354:Molar mass
234:61H4T033E5
205:ChemSpider
165:IUPHAR/BPS
120:CAS Number
103:IUPAC name
1503:β-Alanine
1441:anabolism
1412:Uric acid
1248:anabolism
1045:: 25–33.
629:Pathology
606:manganese
576:Chemistry
545:Synthesis
501:vitamin B
497:vitamin B
65:Drugs.com
1417:Xanthine
1337:(FAICAR)
1325:(SAICAR)
1139:84498320
1094:29181790
1086:12373615
1020:25297304
1012:25030255
792:10727948
707:See also
584:and its
529:in some
517:enzyme,
443:(verify)
185:DrugBank
79:ATC code
1525:thymine
1331:(AICAR)
876:3718672
856:Alcohol
686:smokers
639:ammonia
508:vitamin
487:) is a
359:156.097
321:Formula
194:DB02262
140:PubChem
129:65-86-1
1492:uracil
1319:(CAIR)
1307:(FGAM)
1301:(FGAR)
1283:(PRPP)
1238:purine
1192:(MeSH)
1137:
1092:
1084:
1018:
1010:
874:
790:
701:uracil
612:, and
610:nickel
602:cobalt
554:enzyme
491:and a
392:SMILES
254:C00295
1313:(AIR)
1295:(GAR)
1289:(PRA)
1277:(R5P)
1135:S2CID
1090:S2CID
1016:S2CID
812:(PDF)
697:yeast
690:woman
621:2,2'-
590:anion
412:InChI
368:JSmol
1082:PMID
1008:PMID
957:)".
872:PMID
788:PMID
614:zinc
245:KEGG
225:UNII
174:4690
86:none
61:AHFS
1375:GMP
1370:IMP
1352:AMP
1347:IMP
1264:IMP
1258:R5P
1167:doi
1125:doi
1074:doi
1047:doi
1043:108
1000:doi
969:doi
965:C42
932:doi
903:doi
899:332
864:doi
837:doi
833:123
778:doi
774:267
684:of
652:In
649:.
270:EPA
214:942
154:967
144:CID
1571::
1163:76
1161:.
1133:.
1121:39
1119:.
1115:.
1088:.
1080:.
1070:56
1068:.
1041:.
1014:.
1006:.
996:37
994:.
963:.
930:.
897:.
884:^
870:.
858:.
831:.
786:.
772:.
768:.
740:.
703:.
608:,
604:,
541:.
510:.
503:13
462:ɔː
1527::
1494::
1377::
1372:→
1354::
1349:→
1266::
1261:→
1219:e
1212:t
1205:v
1173:.
1169::
1141:.
1127::
1096:.
1076::
1053:.
1049::
1022:.
1002::
975:.
971::
955:B
951:A
938:.
934::
922:2
909:.
905::
878:.
866::
860:3
843:.
839::
794:.
780::
753:.
483:/
480:k
477:ɪ
474:t
471:ɒ
468:r
465:ˈ
459:/
455:(
370:)
347:4
344:O
341:2
338:N
335:4
332:H
329:5
326:C
272:)
268:(
63:/
20:)
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