5beta-epi-androsterone

ID: ALA4063919

PubChem CID: 134689068

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-/m1/s1

Standard InChI Key:  QGXBDMJGAMFCBF-GYXSFMTNSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    3.1202  -10.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1202  -11.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8255  -12.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8255  -10.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5307  -10.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5273  -11.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2293  -12.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9394  -11.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2363  -10.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9390  -10.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9557   -9.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2415   -9.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6584   -9.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6496  -10.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4208  -10.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9063  -10.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4351   -9.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6960   -8.6975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6531   -8.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6448  -11.3458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9308  -10.1117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292  -11.3292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5193  -12.5509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5234  -10.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4131  -12.1475    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  1
  5 24  1  1
  2 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4063919

   ---

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