(2'R,8R,9S,13S,14S)-3-hydroxy-5',5',13-trimethyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one

ID: ALA515032

Chembl Id: CHEMBL515032

PubChem CID: 11417322

Max Phase: Preclinical

Molecular Formula: C24H32O3

Molecular Weight: 368.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC[C@@]2(CC[C@H]3[C@@H]4CCc5cc(O)ccc5[C@H]4CC[C@@]32C)OC1=O

Standard InChI:  InChI=1S/C24H32O3/c1-22(2)12-13-24(27-21(22)26)11-9-20-19-6-4-15-14-16(25)5-7-17(15)18(19)8-10-23(20,24)3/h5,7,14,18-20,25H,4,6,8-13H2,1-3H3/t18-,19-,20+,23+,24-/m1/s1

Standard InChI Key:  DXLSQWPBMJRKEP-PJPYIVHJSA-N

Alternative Forms

1. Parent:

   

   ALA515032

   (8R,9S,13S,14S,17R)-3-hydroxy-3',3',13-trimethylspiro[7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17,6'-oxane]-2'-one

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: 368.52

Molecular Weight (Monoisotopic): 368.2351

AlogP: 5.35

#Rotatable Bonds: ┄

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.33

CX Basic pKa: ┄

CX LogP: 5.88

CX LogD: 5.88

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: 2.07

References

1. Bydal P, Luu-The V, Labrie F, Poirier D..  (2009)  Steroidal lactones as inhibitors of 17beta-hydroxysteroid dehydrogenase type 5: chemical synthesis, enzyme inhibitory activity, and assessment of estrogenic and androgenic activities.,  44  (2): [PMID:18472187] [10.1016/j.ejmech.2008.03.020]

2. Bellavance E, Luu-The V, Poirier D..  (2009)  Potent and selective steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 7, an enzyme that catalyzes the reduction of the key hormones estrone and dihydrotestosterone.,  52  (23): [PMID:19772289] [10.1021/jm900921c]

Source

Source(1):

• Scientific Literature