5a-Pregnan-3a,20a-diol

ID: ALA1908029

PubChem CID: 1806961

Max Phase: Preclinical

Molecular Formula: C21H36O2

Molecular Weight: 320.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C

Standard InChI:  InChI=1S/C21H36O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h13-19,22-23H,4-12H2,1-3H3/t13-,14+,15-,16+,17+,18+,19+,20+,21-/m1/s1

Standard InChI Key:  YWYQTGBBEZQBGO-YLFIMSDTSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
  -12.7679    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0534    1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0534    1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7679    2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4823    1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4823    1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3389    2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6244    1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6244    1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3389    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3389    3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6245    3.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9100    3.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9100    2.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1254    2.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6405    2.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1254    3.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9100    3.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7583    1.4251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0534    2.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8054    1.3431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2049    2.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1968    0.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0534    0.1000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8705    4.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4225    4.8152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0635    4.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1377    3.5740    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
 10  2  1  0
  2  3  1  0
  3  7  1  0
  8  9  1  0
  9 10  1  0
 14  8  1  0
  8  7  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 13 18  1  1
  8 19  1  1
  3 20  1  1
 14 21  1  6
  7 22  1  6
  6 23  1  6
  2 24  1  6
 17 25  1  0
 25 26  1  6
 25 27  1  0
 17 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1908029

   (3R,5S,8R,9S,10S,13S,14S,17R)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

Molecule Features

Natural Product: Yes

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: 320.52

Molecular Weight (Monoisotopic): 320.2715

AlogP: 4.39

#Rotatable Bonds: 1

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.78

CX LogD: 3.78

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: 2.45

References

1. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

2. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

Source

Source(1):

• Scientific Literature