17a-Methyl-3-tetrazolo-17a-aza-D-homo-3,5-androstadien-17-one

ID: ALA3753825

PubChem CID: 127029223

Max Phase: Preclinical

Molecular Formula: C21H29N5O

Molecular Weight: 367.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)CC[C@H]2[C@@H]3CC=C4C=C(c5nnn[nH]5)CC[C@]4(C)[C@H]3CC[C@@]21C

Standard InChI:  InChI=1S/C21H29N5O/c1-20-10-8-13(19-22-24-25-23-19)12-14(20)4-5-15-16(20)9-11-21(2)17(15)6-7-18(27)26(21)3/h4,12,15-17H,5-11H2,1-3H3,(H,22,23,24,25)/t15-,16+,17+,20+,21+/m1/s1

Standard InChI Key:  VSQWRSWTFXPDHE-OZMCLOMFSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   -4.4900   -1.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0700    0.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1100    1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600   -1.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9900   -0.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700    1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6100    2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -0.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500    0.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6100   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800   -2.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163   -2.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972    1.3523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0779   -1.3683    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    1.2992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5564    0.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2476    1.5534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7231    1.2832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9220   -0.2036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5695   -0.8522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5700   -1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9900    0.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600    1.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4900    1.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0700    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1100   -1.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2601   -0.1538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5629   -2.3613    0.0000 C   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 24  1  0
 23 11  1  0
 11 12  1  0
  5 13  1  6
 23 14  1  6
 10 15  1  6
  9 16  1  1
 24 17  1  1
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
  2 18  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3753825

   ---

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: 367.50

Molecular Weight (Monoisotopic): 367.2372

AlogP: 3.37

#Rotatable Bonds: 1

Polar Surface Area: 74.77

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.30

CX Basic pKa: ┄

CX LogP: 2.33

CX LogD: 0.74

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.83

Np Likeness Score: 0.87

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