Androsterone-3-acetate

ID: ALA2074705

Cas Number: 1164-95-0

PubChem CID: 101996

Max Phase: Preclinical

Molecular Formula: C21H32O3

Molecular Weight: 332.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1

Standard InChI:  InChI=1S/C21H32O3/c1-13(22)24-15-8-10-20(2)14(12-15)4-5-16-17-6-7-19(23)21(17,3)11-9-18(16)20/h14-18H,4-12H2,1-3H3/t14-,15+,16-,17-,18-,20-,21-/m0/s1

Standard InChI Key:  FDCINQSOYQUNKB-XVYLQWLCSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -5.5319   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2464   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9609   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9609   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2464   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5320   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8175   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1030   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1030   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8175   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8175    0.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1030    0.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885    0.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885   -0.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039   -0.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    0.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039    0.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885    1.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3490    1.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885   -1.0901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1030    0.1473    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8175   -1.0902    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5319    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5320   -2.3277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6754   -1.9152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6754   -2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3899   -3.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9609   -3.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
 10  6  1  0
  6  1  1  0
  1  7  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
  8  7  1  0
 14  8  1  0
 11 12  1  0
 12 13  1  0
 13 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 13 18  1  1
 17 19  2  0
 14 20  1  6
  8 21  1  1
  7 22  1  6
  1 23  1  1
  6 24  1  6
  4 25  1  6
 25 26  1  0
 26 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074705

   ANDROSTERONE ACETATE

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: 332.48

Molecular Weight (Monoisotopic): 332.2351

AlogP: 4.53

#Rotatable Bonds: 1

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.21

CX LogD: 4.21

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: 2.44

References

1. Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL..  (1996)  Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter.,  270  (1): [PMID:8779894] [10.1152/ajprenal.1996.270.2.f326]

2. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

Source

Source(2):

• Scientific Literature
• TP-search Transporter Database