5beta-Androstane-3alpha,16alpha,17beta-triol

ID: ALA1908034

PubChem CID: 11185932

Max Phase: Preclinical

Molecular Formula: C19H32O3

Molecular Weight: 308.46

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](O)[C@H](O)C[C@@H]12

Standard InChI:  InChI=1S/C19H32O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h11-17,20-22H,3-10H2,1-2H3/t11-,12-,13-,14+,15+,16-,17+,18+,19+/m1/s1

Standard InChI Key:  CXGDRQWRJUSSAR-ZUFLAUTESA-N

Molfile:  

     RDKit          2D

 26 29  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
   -8.8705    4.2021    0.0000 O   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
  -10.6244    2.7500    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
   -9.9100    1.5126    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3389    1.5125    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    0.2750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8155    2.7501    0.0000 O   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
 17 18  1  1
 13 19  1  1
  8 20  1  1
  3 21  1  1
 14 22  1  6
  7 23  1  6
  6 24  1  6
  2 25  1  1
 16 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1908034

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

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: 308.46

Molecular Weight (Monoisotopic): 308.2351

AlogP: 2.72

#Rotatable Bonds: ┄

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.62

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: 2.13

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: 2.65

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]

Source

Source(1):

• Scientific Literature