(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((R)-6-methylhept-5-en-2-yl)-4,5,6,7,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

ID: ALA2048336

Chembl Id: CHEMBL2048336

PubChem CID: 13995943

Max Phase: Preclinical

Molecular Formula: C30H48O

Molecular Weight: 424.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3

Standard InChI:  InChI=1S/C30H48O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25H,9,11-19H2,1-8H3/t21-,22-,25+,28-,29-,30+/m1/s1

Standard InChI Key:  OMKJDABLEGUPIE-WUELKCQHSA-N

Alternative Forms

1. Parent:

   

   ALA2048336

   (5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-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: 424.71

Molecular Weight (Monoisotopic): 424.3705

AlogP: 8.69

#Rotatable Bonds: 4

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: 8.27

CX LogD: 8.27

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: 3.38

References

1. 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]

2. Yang X, Chen XJ, Yang Z, Xi YB, Wang L, Wu Y, Yan YB, Rao Y..  (2018)  Synthesis, Evaluation, and Structure-Activity Relationship Study of Lanosterol Derivatives To Reverse Mutant-Crystallin-Induced Protein Aggregation.,  61  (19): [PMID:30153006] [10.1021/acs.jmedchem.8b00705]

Source

Source(1):

• Scientific Literature