(S)-17-Hydroxy-13-methyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

ID: ALA2311179

Cas Number: 6218-29-7

PubChem CID: 11747706

Product Number: D136436, Order Now?

Max Phase: Preclinical

Molecular Formula: C18H24O2

Molecular Weight: 272.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CCC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O

Standard InChI:  InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,15-17,20H,2-9H2,1H3/t15-,16+,17+,18+/m1/s1

Standard InChI Key:  PUQSDJZESAQGQS-OWSLCNJRSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  1  0  0  0  0  0999 V2000
    4.7417   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0250   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -2.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0250   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -2.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4375   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -4.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3542   -1.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -2.8792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -4.1167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  9  1  0
  4  2  1  0
  5  1  1  0
  6  5  1  0
  7  4  2  0
  8  1  1  0
  9  8  1  0
 10  2  1  0
 11  5  1  0
 12  6  1  0
 13  3  1  0
 14 11  1  0
 15 18  1  0
 16 12  1  0
 17 15  2  0
 18 10  1  0
  3 19  1  1
 13 20  1  1
  3  6  1  0
  4 14  1  0
 16 13  1  0
 15  7  1  0
  5 21  1  1
  6 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2311179

   9(10)-Dehydronandrolone

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: 272.39

Molecular Weight (Monoisotopic): 272.1776

AlogP: 3.55

#Rotatable Bonds: ┄

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.62

CX LogD: 2.62

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.73

Np Likeness Score: 2.57

References

1. Waszkowycz B, Clark DE, Frenkel D, Li J, Murray CW, Robson B, Westhead DR..  (1994)  PRO_LIGAND: an approach to de novo molecular design. 2. Design of novel molecules from molecular field analysis (MFA) models and pharmacophores.,  37  (23): [PMID:7966160] [10.1021/jm00049a019]

2. Doré JC, Gilbert J, Ojasoo T, Raynaud JP..  (1986)  Correspondence analysis applied to steroid receptor binding.,  29  (1): [PMID:3001307] [10.1021/jm00151a009]

3. Muddana SS, Price AM, MacBride MM, Peterson BR..  (2004)  11beta-alkyl-Delta9-19-nortestosterone derivatives: high-affinity ligands and potent partial agonists of the androgen receptor.,  47  (21): [PMID:15456242] [10.1021/jm0342515]

Source

Source(1):

• Scientific Literature