3-Tetrazolo-3,5-pregnadien-20-one

ID: ALA3753791

PubChem CID: 127028927

Max Phase: Preclinical

Molecular Formula: C22H30N4O

Molecular Weight: 366.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)C1CC[C@H]2[C@@H]3CC=C4C=C(c5nnn[nH]5)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C22H30N4O/c1-13(27)17-6-7-18-16-5-4-15-12-14(20-23-25-26-24-20)8-10-21(15,2)19(16)9-11-22(17,18)3/h4,12,16-19H,5-11H2,1-3H3,(H,23,24,25,26)/t16-,17?,18-,19-,21-,22+/m0/s1

Standard InChI Key:  CBSJGFZRZULEDU-VXTLHUCTSA-N

Molfile:  

     RDKit          2D

 30 34  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
   -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
    3.3007    4.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2604    4.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3386    4.6401    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  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
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 23  1  0
  2 23  1  0
 17 28  1  0
 28 29  1  0
 28 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3753791

   ---

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: 366.51

Molecular Weight (Monoisotopic): 366.2420

AlogP: 4.36

#Rotatable Bonds: 2

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: 3.76

CX LogD: 2.16

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.84

Np Likeness Score: 1.35

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