EPB

7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[1-METHYL-2-(2-METHYL-THIAZOL-4-YL)VINYL]-4,17-DIOXABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE

Created: 2003-08-07
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count76
Chiral Atom Count7
Bond Count78
Aromatic Bond Count5
2D diagram of EPB
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Chemical Component Summary

Name7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[1-METHYL-2-(2-METHYL-THIAZOL-4-YL)VINYL]-4,17-DIOXABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE
SynonymsEPOTHILONE B
Systematic Name (OpenEye OEToolkits)(1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-1,5,7,9,9-pentamethyl-14-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-13,17-dioxabicyclo[14.1.0]heptadecane-8,12-dione
FormulaC27 H41 N O6 S
Molecular Weight507.683
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C1C(C)C(O)C(C)CCCC3(OC3CC(OC(=O)CC(O)C1(C)C)/C(=C/c2nc(sc2)C)C)C
SMILESCACTVS3.341C[CH]1CCC[C]2(C)O[CH]2C[CH](OC(=O)C[CH](O)C(C)(C)C(=O)[CH](C)[CH]1O)C(C)=Cc3csc(C)n3
SMILESOpenEye OEToolkits1.5.0Cc1nc(cs1)C=C(C)C2CC3C(O3)(CCCC(C(C(C(=O)C(C(CC(=O)O2)O)(C)C)C)O)C)C
Canonical SMILESCACTVS3.341 C[C@H]1CCC[C@@]2(C)O[C@H]2C[C@H](OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)\C(C)=C\c3csc(C)n3
Canonical SMILESOpenEye OEToolkits1.5.0 Cc1nc(cs1)\C=C(/C)\[C@@H]2C[C@H]3[C@](O3)(CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](CC(=O)O2)O)(C)C)C)O)C)C
InChIInChI1.03 InChI=1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
InChIKeyInChI1.03 QXRSDHAAWVKZLJ-PVYNADRNSA-N

Drug Info: DrugBank

DrugBank IDDB03010 
NamePatupilone
Groups
  • experimental
  • investigational
DescriptionEpothilone B is a 16-membered macrolide that mimics the biological effects of taxol.
Synonyms
  • Epothilone B
  • Patupilone
  • patupilona
  • (−)-epothilone B
  • Epo B
IndicationInvestigated for use/treatment in ovarian cancer, lung cancer, brain cancer, breast cancer, and gastric cancer.
Categories
  • Anti-Bacterial Agents
  • Antimitotic Agents
  • Antineoplastic Agents
  • Cytochrome P-450 CYP3A Inhibitors
  • Cytochrome P-450 CYP3A4 Inhibitors
CAS number152044-54-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Tubulin alpha 3C/D chainMRECISIHVGQAGVQIGNACWELYCLEHGIQPDGQMPSDKTIGGGDDSFN...unknown
Tubulin beta chainMREIVHIQAGQCGNQIGAKFWEVISDEHGIDPTGTYHGDSDLQLDRISVY...unknown
Tubulin beta-1 chainMREIVHIQIGQCGNQIGAKFWEMIGEEHGIDLAGSDRGASALQLERISVY...unknown
Tubulin beta-4B chainMREIVHLQAGQCGNQIGAKFWEVISDEHGIDPTGTYHGDSDLQLERINVY...unknown
Tubulin beta-4A chainMREIVHLQAGQCGNQIGAKFWEVISDEHGIDPTGTYHGDSDLQLERINVY...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 448013
ChEMBL CHEMBL94657
ChEBI CHEBI:31550, CHEBI:94639