Molecule ID: 9982260

IUPAC Name: methyl (3S,5S,8S,9S,10R,13R,14R)-3-acetyloxy-17-hydroxy-4,4,8,10,12,13,16-heptamethyl-15-oxo-2,3,5,6,7,9-hexahydro-1H-cyclopenta[a]phenanthrene-14-carboxylate

Description: The molecule is a 17-oxosteroid that is 17-oxo-5beta,9beta,10alpha,13alpha-androsta-11,15-dieneandroxta-11,15-diene which is substituted by an acetoxy group at the 3beta position, methyl groups at the 4, 4, 8, 12, and 16 positions, a methoxycarbonyl group at position 14, and a hydroxy group at position 15. A farnesyltransferase inhibitor produced by Penicillium roqueforti, a filamentous fungus involved in the ripening of several kinds of blue cheeses. It has a role as an EC 2.5.1.58 (protein farnesyltransferase) inhibitor and a Penicillium metabolite. It is a 15-hydroxy steroid, a 17-oxo steroid, a 5beta steroid, an acetate ester, an enol, a meroterpenoid and a methyl ester. It is a conjugate acid of an andrastin C(1-).

SMILES: COC(=O)[C@@]12C(=O)C(C)=C(O)[C@]1(C)C(C)=C[C@H]1[C@]3(C)CC[C@H](OC(C)=O)C(C)(C)[C@H]3CC[C@@]12C

SELFIES: [C][O][C][=Branch1][C][=O][C@@][C][=Branch1][C][=O][C][Branch1][C][C][=C][Branch1][C][O][C@][Ring1][Branch2][Branch1][C][C][C][Branch1][C][C][=C][C@H1][C@][Branch1][C][C][C][C][C@H1][Branch1][#Branch1][O][C][Branch1][C][C][=O][C][Branch1][C][C][Branch1][C][C][C@H1][Ring1][=N][C][C][C@@][Ring1][P][Ring2][Ring1][=N][C]

InChI: InChI=1S/C28H40O6/c1-15-14-19-25(6)12-11-20(34-17(3)29)24(4,5)18(25)10-13-26(19,7)28(23(32)33-9)22(31)16(2)21(30)27(15,28)8/h14,18-20,30H,10-13H2,1-9H3/t18-,19+,20+,25-,26+,27+,28-/m1/s1

Molecular Properties:
- Polar Surface Area: 89.9 Ų
- LogP: 5.2