Epothilone D, Microtubule-stabilizing agent

Key facts

CAS number

189453-10-9

Molecular weight

491.7 Da

Molecular formula

C₂₇H₄₁NO₅S

PubChem

447865

Nature

Synthetic

Solubility

Soluble in ethanol to 100 mM

Soluble in DMSO to 100 mM

Biochemical name

Epothilone D

Biological description

Microtubule-stabilizing agent. Epothilone A (ab143615) and B (ab141271) analog. Improves microtubule density and axonal integrity Shows antineoplastic and neuroprotective effects in vivo. Blood-brain barrier permeable.

Canonical smiles

CC1CCCC(=CCC(OC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC2=CSC(=N2)C)C)C

Isomeric smiles

C[C@H]1CCC/C(=C\C[C@H](OC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C2=CSC(=N2)C)/C)/C

InChi

InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1

InChiKey

XOZIUKBZLSUILX-GIQCAXHBSA-N

IUPAC Name

(4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione