Benzoic acid 1,7-diacetoxy-17-[6-(1-hydroxy-1-methyl-ethyl)-6-methoxy-tetrahydro-pyran-3-yl]-4,4,8,10,13-pentamethyl-2,3,4,5,6,7,8,9,10,11,1enta[a]phenanthren-3-yl ester

ID: ALA297724

Chembl Id: CHEMBL297724

PubChem CID: 44297559

Max Phase: Preclinical

Molecular Formula: C42H60O9

Molecular Weight: 708.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@]1(C(C)(C)O)CC[C@@H]([C@@H]2CC=C3[C@@]4(C)C(CC[C@]32C)[C@]2(C)C(C[C@H]4OC(C)=O)C(C)(C)C(OC(=O)c3ccccc3)C[C@@H]2OC(C)=O)CO1

Standard InChI:  InChI=1S/C42H60O9/c1-25(43)49-34-22-32-37(3,4)33(51-36(45)27-14-12-11-13-15-27)23-35(50-26(2)44)41(32,9)31-19-20-39(7)29(16-17-30(39)40(31,34)8)28-18-21-42(47-10,48-24-28)38(5,6)46/h11-15,17,28-29,31-35,46H,16,18-24H2,1-10H3/t28-,29+,31?,32?,33?,34-,35+,39+,40+,41-,42-/m1/s1

Standard InChI Key:  PQDUWMNIBOUULA-BYSQBQSXSA-N

Alternative Forms

1. Parent:

   

   ALA297724

   [(1S,7R,8R,10S,13S,17S)-1,7-diacetyloxy-17-[(3S,6R)-6-(2-hydroxypropan-2-yl)-6-methoxyoxan-3-yl]-4,4,8,10,13-pentamethyl-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] benzoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 708.93

Molecular Weight (Monoisotopic): 708.4237

AlogP: 7.44

#Rotatable Bonds: 7

Polar Surface Area: 117.59

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.37

CX Basic pKa: ┄

CX LogP: 6.48

CX LogD: 6.48

Aromatic Rings: 1

Heavy Atoms: 51

QED Weighted: 0.18

Np Likeness Score: 2.26

References

1. Lu Zeng, Zhe-ming Gu, Ching-jer Chang, Smith DL, McLaughlin JL.  (1995)  A pair of new apotirucallane triterpenes, meliavolkensins A and B, from Melia volkensii (Meliaceae),  5  (2): [10.1016/0960-894X(95)00004-D]

Source

Source(1):

• Scientific Literature