(3S,20R)-20-(Propylamino-ethyl)-pregn-7-en-3-ol

ID: ALA595251

PubChem CID: 46225920

Max Phase: Preclinical

Molecular Formula: C26H45NO

Molecular Weight: 387.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C26H45NO/c1-5-15-27-16-12-18(2)22-8-9-23-21-7-6-19-17-20(28)10-13-25(19,3)24(21)11-14-26(22,23)4/h7,18-20,22-24,27-28H,5-6,8-17H2,1-4H3/t18-,19+,20+,22-,23+,24+,25+,26-/m1/s1

Standard InChI Key:  WQHXMCZCMKJPHZ-QSNVUPPFSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    6.9707   -1.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9707   -0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6866    0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6866   -1.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3983   -1.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1142   -1.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8300   -1.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8300   -0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5417    0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3264   -0.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8153    0.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3271    1.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2938    2.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9888    2.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5417    1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5417    1.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8300    1.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1142    1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1142    0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3983   -0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3983    0.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1142   -0.6136    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5417   -0.6136    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5626    2.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2564   -1.4389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7207    2.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1208    1.5083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3917   -1.8500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4163    2.6212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1483    2.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8439    2.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5758    2.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
  9 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
  8 19  1  0
 19 20  1  0
  3 20  1  0
  5 20  1  0
 20 21  1  1
 19 22  1  6
  9 23  1  6
 13 24  1  6
  1  2  1  0
  1 25  1  1
  2  3  1  0
 14 26  1  0
  1  4  1  0
 12 27  1  6
  4  5  1  0
  5 28  1  6
  5  6  1  0
 26 29  1  0
  6  7  1  0
 29 30  1  0
  7  8  2  0
 30 31  1  0
  8  9  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA595251

   (3S,5S,9R,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-4-(propylamino)butan-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

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: 387.65

Molecular Weight (Monoisotopic): 387.3501

AlogP: 5.95

#Rotatable Bonds: 6

Polar Surface Area: 32.26

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.75

CX LogP: 5.26

CX LogD: 2.27

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: 2.38

References

1. Renard D, Perruchon J, Giera M, Müller J, Bracher F..  (2009)  Side chain azasteroids and thiasteroids as sterol methyltransferase inhibitors in ergosterol biosynthesis.,  17  (23): [PMID:19833521] [10.1016/j.bmc.2009.09.037]

Source

Source(1):

• Scientific Literature