(25R)-26-Hydroxy-12,22-dioxo-5alpha-cholestan-3beta,16beta-diyldiacetate

ID: ALA1092068

PubChem CID: 46885888

Max Phase: Preclinical

Molecular Formula: C31H48O7

Molecular Weight: 532.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC(=O)[C@]2(C)[C@@H]([C@H](C)C(=O)CC[C@@H](C)CO)[C@@H](OC(C)=O)C[C@@H]32)C1

Standard InChI:  InChI=1S/C31H48O7/c1-17(16-32)7-10-26(35)18(2)29-27(38-20(4)34)14-25-23-9-8-21-13-22(37-19(3)33)11-12-30(21,5)24(23)15-28(36)31(25,29)6/h17-18,21-25,27,29,32H,7-16H2,1-6H3/t17-,18-,21+,22+,23-,24+,25+,27+,29+,30+,31-/m1/s1

Standard InChI Key:  PJEIZYOGVHHVCL-KINUGENKSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1092068

   [(3S,5S,8R,9S,10S,13S,14S,16S,17R)-16-acetyloxy-17-[(2S,6R)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-10,13-dimethyl-12-oxo-1,2,3,4,5,6,7,8,9,11,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate

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: 532.72

Molecular Weight (Monoisotopic): 532.3400

AlogP: 4.91

#Rotatable Bonds: 8

Polar Surface Area: 106.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.14

CX LogD: 4.14

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.44

Np Likeness Score: 2.31

References

1. Fernández-Herrera MA, López-Muñoz H, Hernández-Vázquez JM, López-Dávila M, Escobar-Sánchez ML, Sánchez-Sánchez L, Pinto BM, Sandoval-Ramírez J..  (2010)  Synthesis of 26-hydroxy-22-oxocholestanic frameworks from diosgenin and hecogenin and their in vitro antiproliferative and apoptotic activity on human cervical cancer CaSki cells.,  18  (7): [PMID:20303770] [10.1016/j.bmc.2010.02.051]

2. Fernández-Herrera MA, Mohan S, López-Muñoz H, Hernández-Vázquez JM, Pérez-Cervantes E, Escobar-Sánchez ML, Sánchez-Sánchez L, Regla I, Pinto BM, Sandoval-Ramírez J..  (2010)  Synthesis of the steroidal glycoside (25R)-3β,16β-diacetoxy-12,22-dioxo-5α-cholestan-26-yl β-D-glucopyranoside and its anti-cancer properties on cervicouterine HeLa, CaSki, and ViBo cells.,  45  (11): [PMID:20801554] [10.1016/j.ejmech.2010.07.051]

Source

Source(1):

• Scientific Literature