(5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one

ID: ALA69851

Chembl Id: CHEMBL69851

Cas Number: 601-53-6

PubChem CID: 92132

Max Phase: Preclinical

Molecular Formula: C27H46O

Molecular Weight: 386.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,22-25H,6-17H2,1-5H3/t19-,20-,22+,23-,24+,25+,26+,27-/m1/s1

Standard InChI Key:  PESKGJQREUXSRR-JDIFZLMISA-N

Alternative Forms

1. Parent:

   

   ALA69851

   5beta-Cholestan-3-one

Molecule Features

Natural Product: Yes

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: 386.66

Molecular Weight (Monoisotopic): 386.3549

AlogP: 7.68

#Rotatable Bonds: 5

Polar Surface Area: 17.07

Molecular Species: NEUTRAL

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.73

CX LogD: 7.73

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: 2.14

References

1. Suzuki K, Shimizu T, Nakata T..  (1998)  The cholesterol metabolite cholest-4-en-3-one and its 3-oxo derivatives suppress body weight gain, body fat accumulation and serum lipid concentration in mice.,  8  (16): [PMID:9873500] [10.1016/s0960-894x(98)00362-x]

2. Johnston JB, Singh AA, Clary AA, Chen CK, Hayes PY, Chow S, De Voss JJ, Ortiz de Montellano PR..  (2012)  Substrate analog studies of the ω-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1.,  20  (13): [PMID:22647881] [10.1016/j.bmc.2012.05.003]

Source

Source(1):

• Scientific Literature