(3R,5S,8R,9S,10S,13R,14S)-3-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one

ID: ALA4086229

PubChem CID: 12306761

Max Phase: Preclinical

Molecular Formula: C19H30O2

Molecular Weight: 290.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19+/m0/s1

Standard InChI Key:  QGXBDMJGAMFCBF-AZERQAKLSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    3.7063  -16.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7063  -17.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4115  -18.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4115  -16.5419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1168  -16.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133  -17.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8154  -18.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5254  -17.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8223  -16.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5250  -16.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5418  -15.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8276  -15.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2445  -15.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2356  -16.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0068  -16.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4924  -16.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0212  -15.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2821  -14.7315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2392  -14.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2309  -17.3798    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5169  -16.1457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8153  -17.3633    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1054  -18.5849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1095  -16.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9991  -18.1815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 17 18  2  0
 13 19  1  6
 14 20  1  6
 10 21  1  1
  9 22  1  6
  6 23  1  6
  5 24  1  1
  2 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4086229

   Androsterine

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: 290.45

Molecular Weight (Monoisotopic): 290.2246

AlogP: 3.96

#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: 3.77

CX LogD: 3.77

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: 2.66

References

1. Cortés-Benítez F, Roy J, Maltais R, Poirier D..  (2017)  Impact of androstane A- and D-ring inversion on 17β-hydroxysteroid dehydrogenase type 3 inhibitory activity, androgenic effect and metabolic stability.,  25  (7): [PMID:28254377] [10.1016/j.bmc.2017.02.008]

Source

Source(1):

• Scientific Literature