Molecule ID: 6505803

IUPAC Name: [(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-(prop-2-enylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate

Description: The molecule is a 19-membered macrocyle that is geldanamycin in which the methoxy substituent attached to the benzoquinone moiety has been replaced by an allylamino group. It is a potent inhibitor of heat shock protein 90 (Hsp90). A less toxic analogue than geldanamycin, it induces apoptosis and displays antitumour effects. It has a role as an antineoplastic agent, a Hsp90 inhibitor and an apoptosis inducer. It is a secondary amino compound, an ansamycin, a carbamate ester, an organic heterobicyclic compound and a member of 1,4-benzoquinones. It derives from a geldanamycin.

SMILES: C=CCNC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(=N)O)[C@@H](OC)/C=C\C=C(/C)C(O)=NC(=CC1=O)C2=O

SELFIES: [C][=C][C][N][C][=C][C][C@@H1][Branch1][C][C][C][C@H1][Branch1][Ring1][O][C][C@H1][Branch1][C][O][C@@H1][Branch1][C][C][/C][=C][Branch1][C][\C][C@H1][Branch1][#Branch1][O][C][=Branch1][C][=N][O][C@@H1][Branch1][Ring1][O][C][/C][=C][\C][=C][Branch1][C][/C][C][Branch1][C][O][=N][C][=Branch1][#Branch1][=C][C][Ring2][Ring2][Ring1][=O][C][Ring2][Ring2][Ring2][=O]

InChI: InChI=1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1

Molecular Properties:
- Polar Surface Area: 166.0 Ų
- LogP: 2.6