Ansamitocin P-3, microtubule depolymerizing agent

Key facts

CAS number

66584-72-3

Purity

>95%

Form

Solid

form

Molecular weight

635.1 Da

Molecular formula

C₃₂H₄₃ClN₂O₉

PubChem

5282049

Nature

Synthetic

Solubility

Soluble in DMSO

Biochemical name

Ansamitocin P-3

Biological description

Potent microtubule depolymerizing agent. Binds to tubulin at the vinblastine (ab145649) site. Induces p53-mediated apoptosis. Shows cytotoxic effects to tumor cell lines. Maytansine analog. Shows antitumor effects in vivo. Orally active.

Canonical smiles

CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)C)C)C)OC)(NC(=O)O2)O

Isomeric smiles

C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)C(C)C)C)\C)OC)(NC(=O)O2)O

InChi

InChI=1S/C32H43ClN2O9/c1-17(2)29(37)43-25-15-26(36)35(6)21-13-20(14-22(40-7)27(21)33)12-18(3)10-9-11-24(41-8)32(39)16-23(42-30(38)34-32)19(4)28-31(25,5)44-28/h9-11,13-14,17,19,23-25,28,39H,12,15-16H2,1-8H3,(H,34,38)/b11-9+,18-10+/t19-,23+,24-,25+,28+,31+,32+/m1/s1

InChiKey

OPQNCARIZFLNLF-JBHFWYGFSA-N

IUPAC Name

[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-methylpropanoate