Knowledge (XXG)

Purmorphamine

Source ๐Ÿ“

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InChI=1S/C31H32N6O2/c1-2-9-25(10-3-1)37-21-32-28-29(33-23-13-15-24(16-14-23)36-17-19-38-20-18-36)34-31(35-30(28)37)39-27-12-6-8-22-7-4-5-11-26(22)27/h4-8,11-16,21,25H,1-3,9-10,17-20H2,(H,33,34,35)
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Aravamudhan A, Ramos DM, Nip J, Subramanian A, James R, Harmon MD, et al. (2013). "Osteoinductive small molecules: growth factor alternatives for bone tissue engineering".
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Sharma S, Kaur A, Sharma S (April 2018). "Preconditioning potential of purmorphamine: a hedgehog activator against ischaemic reperfusion injury in ovariectomised rat heart".
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Wu X, Ding S, Ding Q, Gray NS, Schultz PG (December 2002). "A small molecule with osteogenesis-inducing activity in multipotent mesenchymal progenitor cells".
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Lee SJ, Lee HK, Cho SY, Choi JK, Shin HK, Kwak EJ, et al. (October 2008). "Identification of osteogenic purmorphamine derivatives".
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and brain development as well as having a number of other functions in the body. Purmorphamine has been shown to induce
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Stanton BZ, Peng LF (January 2010). "Small-molecule modulators of the Sonic Hedgehog signaling pathway".
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Sinha S, Chen JK (January 2006). "Purmorphamine activates the Hedgehog pathway by targeting Smoothened".
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in bone tissue as well as influencing growth and differentiation of neurons in the brain.
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C1(N(C2CCCCC2)C=N3)=C3C(NC4=CC=C(N5CCOCC5)C=C4)=NC(OC6=CC=CC7=C6C=CC=C7)=N1
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9-cyclohexyl-N-(4-morpholinophenyl)-2-(naphthalen-1-yloxy)-9H-purin-6-amine
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was the first small-molecule agonist developed for the protein
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Wu X, Walker J, Zhang J, Ding S, Schultz PG (September 2004).
151: 228: 215: 182: 177: 145: 125: 105: 80: 60: 35: 94: 69: 8: 19: 165: 114: 385: 134: 335:Journal of the American Chemical Society 325: 279: 259: 161: 49: 18: 7: 308:, which is involved in bone growth, 85: 14: 200: 194: 27: 287:Key:FYBHCRQFSFYWPY-UHFFFAOYSA-N 387:10.1016/j.chembiol.2004.06.010 206: 188: 1: 516:Current Pharmaceutical Design 528:10.2174/1381612811319190008 310:cardiovascular regeneration 615: 306:hedgehog signaling pathway 178:Chemical and physical data 270: 250: 40: 26: 563:10.1177/0267659117732401 411:Nature Chemical Biology 374:Chemistry & Biology 481:Molecular BioSystems 304:, a key part of the 454:Molecules and Cells 423:10.1038/nchembio753 23: 599:Receptor agonists 347:10.1021/ja0283908 295: 294: 241:Interactive image 147:CompTox Dashboard 16:Chemical compound 606: 583: 582: 546: 540: 539: 511: 505: 504: 493:10.1039/b910196a 476: 470: 469: 449: 443: 442: 406: 400: 399: 389: 365: 359: 358: 330: 243: 223: 208: 202: 196: 190: 170: 169: 155: 153: 138: 118: 98: 88: 87: 73: 31: 24: 22: 614: 613: 609: 608: 607: 605: 604: 603: 589: 588: 587: 586: 548: 547: 543: 513: 512: 508: 478: 477: 473: 451: 450: 446: 408: 407: 403: 367: 366: 362: 341:(49): 14520โ€“1. 332: 331: 327: 322: 291: 288: 283: 278: 277: 266: 263: 258: 257: 246: 221: 211: 205: 199: 193: 173: 149: 141: 121: 101: 84: 76: 56: 53: 48: 47: 17: 12: 11: 5: 612: 610: 602: 601: 591: 590: 585: 584: 557:(3): 209โ€“218. 541: 522:(19): 3420โ€“8. 506: 471: 444: 401: 380:(9): 1229โ€“38. 360: 324: 323: 321: 318: 293: 292: 290: 289: 286: 284: 281: 273: 272: 271: 268: 267: 265: 264: 261: 253: 252: 251: 248: 247: 245: 244: 236: 234: 226: 225: 219: 213: 212: 209: 203: 197: 191: 186: 180: 179: 175: 174: 172: 171: 163:DTXSID20415293 158: 156: 143: 142: 140: 139: 131: 129: 123: 122: 120: 119: 111: 109: 103: 102: 100: 99: 91: 89: 78: 77: 75: 74: 66: 64: 58: 57: 55: 54: 51: 43: 42: 41: 38: 37: 33: 32: 15: 13: 10: 9: 6: 4: 3: 2: 611: 600: 597: 596: 594: 580: 576: 572: 568: 564: 560: 556: 552: 545: 542: 537: 533: 529: 525: 521: 517: 510: 507: 502: 498: 494: 490: 486: 482: 475: 472: 467: 463: 459: 455: 448: 445: 440: 436: 432: 428: 424: 420: 416: 412: 405: 402: 397: 393: 388: 383: 379: 375: 371: 364: 361: 356: 352: 348: 344: 340: 336: 329: 326: 319: 317: 315: 311: 307: 303: 299: 298:Purmorphamine 285: 280: 276: 269: 260: 256: 249: 242: 238: 237: 235: 232: 227: 220: 218: 214: 187: 185: 181: 176: 168: 164: 160: 159: 157: 148: 144: 137: 133: 132: 130: 128: 124: 117: 113: 112: 110: 108: 104: 97: 93: 92: 90: 83: 79: 72: 68: 67: 65: 63: 59: 50: 46: 39: 34: 30: 25: 21:Purmorphamine 554: 550: 544: 519: 515: 509: 487:(1): 44โ€“54. 484: 480: 474: 460:(4): 380โ€“6. 457: 453: 447: 417:(1): 29โ€“30. 414: 410: 404: 377: 373: 363: 338: 334: 328: 314:osteogenesis 297: 296: 224: gยทmol 71:483367-10-8 36:Identifiers 320:References 302:Smoothened 229:3D model ( 217:Molar mass 136:PB12M2F8KY 107:ChemSpider 62:CAS Number 45:IUPAC name 551:Perfusion 593:Category 571:29065787 536:23432678 501:20024066 466:18695357 439:29035911 431:16408088 396:15380183 355:12465946 579:3978923 222:520.637 184:Formula 116:4447411 96:5284329 82:PubChem 577:  569:  534:  499:  464:  437:  429:  394:  353:  255:SMILES 575:S2CID 435:S2CID 275:InChI 231:JSmol 567:PMID 532:PMID 497:PMID 462:PMID 427:PMID 392:PMID 351:PMID 127:UNII 559:doi 524:doi 489:doi 419:doi 382:doi 343:doi 339:124 152:EPA 86:CID 595:: 573:. 565:. 555:33 553:. 530:. 520:19 518:. 495:. 483:. 458:26 456:. 433:. 425:. 413:. 390:. 378:11 376:. 372:. 349:. 337:. 198:32 192:31 581:. 561:: 538:. 526:: 503:. 491:: 485:6 468:. 441:. 421:: 415:2 398:. 384:: 357:. 345:: 233:) 210:2 207:O 204:6 201:N 195:H 189:C 154:) 150:(

Index


IUPAC name
CAS Number
483367-10-8
PubChem
5284329
ChemSpider
4447411
UNII
PB12M2F8KY
CompTox Dashboard
DTXSID20415293
Edit this at Wikidata
Formula
Molar mass
JSmol
Interactive image
SMILES
InChI
Smoothened
hedgehog signaling pathway
cardiovascular regeneration
osteogenesis
doi
10.1021/ja0283908
PMID
12465946
"Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway"
doi
10.1016/j.chembiol.2004.06.010

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