3-Tetrazolo-3,5-androstadien-17-one

ID: ALA3754525

PubChem CID: 127026663

Max Phase: Preclinical

Molecular Formula: C20H26N4O

Molecular Weight: 338.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CCC(c3nnn[nH]3)=CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12

Standard InChI:  InChI=1S/C20H26N4O/c1-19-9-7-12(18-21-23-24-22-18)11-13(19)3-4-14-15-5-6-17(25)20(15,2)10-8-16(14)19/h3,11,14-16H,4-10H2,1-2H3,(H,21,22,23,24)/t14-,15-,16-,19-,20-/m0/s1

Standard InChI Key:  HVXDOJKJRIHIDP-UKSSEWCLSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   -4.1792   -0.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1792   -1.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9382   -2.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9565    0.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -0.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197   -2.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -1.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    0.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8030   -0.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8030    2.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4562    1.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    1.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    0.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625    0.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625    1.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032    2.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930    0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    2.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715   -0.8608    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4332   -0.6715    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2979   -0.6205    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2968    3.7367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4819   -2.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6240   -4.0690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0920   -4.3768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8385   -3.0757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8317   -1.9638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5  9  1  0
  6  7  2  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
  5 18  1  1
 13 19  1  1
 10 20  1  1
  9 21  1  6
 14 22  1  6
 17 23  2  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  1  0
  2 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3754525

   ---

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: 338.45

Molecular Weight (Monoisotopic): 338.2107

AlogP: 3.72

#Rotatable Bonds: 1

Polar Surface Area: 71.53

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.30

CX Basic pKa: ┄

CX LogP: 3.54

CX LogD: 1.94

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.85

Np Likeness Score: 1.23

References

1. Aggarwal S, Mahapatra MK, Kumar R, Bhardwaj TR, Hartmann RW, Haupenthal J, Kumar M..  (2016)  Synthesis and biological evaluation of 3-tetrazolo steroidal analogs: Novel class of 5α-reductase inhibitors.,  24  (4): [PMID:26780831] [10.1016/j.bmc.2015.12.048]

Source

Source(1):

• Scientific Literature