17alpha-Azidomethyl-5alpha-androstane-3beta,17beta-diol

ID: ALA4165826

PubChem CID: 145955408

Max Phase: Preclinical

Molecular Formula: C20H33N3O2

Molecular Weight: 347.50

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@H]1CC[C@@]2(O)CN=[N+]=[N-]

Standard InChI:  InChI=1S/C20H33N3O2/c1-18-8-5-14(24)11-13(18)3-4-15-16(18)6-9-19(2)17(15)7-10-20(19,25)12-22-23-21/h13-17,24-25H,3-12H2,1-2H3/t13-,14-,15+,16-,17-,18-,19-,20+/m0/s1

Standard InChI Key:  ZHCLTKLTERIZLM-MYDRVZFISA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    6.2940   -3.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0038   -3.6697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9646   -5.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9646   -6.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6740   -6.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6740   -5.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -5.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3758   -6.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0820   -6.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7961   -6.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0889   -5.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7957   -5.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125   -3.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0942   -4.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5193   -4.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5104   -5.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2858   -5.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7755   -4.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533   -6.7738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3719   -4.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7876   -4.7257    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5140   -3.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678   -7.1773    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0818   -5.9515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5057   -5.9680    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9997   -2.8525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -2.0353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9874   -1.2175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  1  0
  4  7  1  0
  5  6  1  0
  6  9  1  0
  8  7  1  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12 13  1  0
 12 15  1  0
 13 17  1  0
 16 14  1  0
 14 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
  2 16  1  0
  5 20  1  1
  8 21  1  1
 13 22  1  1
 16 23  1  1
  9 24  1  6
 12 25  1  6
 17 26  1  6
  1 27  1  0
 27 28  2  0
 28 29  2  0
M  CHG  2  28   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4165826

   ---

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: 347.50

Molecular Weight (Monoisotopic): 347.2573

AlogP: 4.43

#Rotatable Bonds: 2

Polar Surface Area: 89.22

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.81

CX Basic pKa: ┄

CX LogP: 3.26

CX LogD: 3.14

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.44

Np Likeness Score: 2.19

References

1. Romero-Hernández LL, Merino-Montiel P, Meza-Reyes S, Vega-Baez JL, López Ó, Padrón JM, Montiel-Smith S..  (2018)  Synthesis of unprecedented steroidal spiro heterocycles as potential antiproliferative drugs.,  143  [PMID:29172080] [10.1016/j.ejmech.2017.10.063]

Source

Source(1):

• Scientific Literature