10,13,17-Trimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA40294

PubChem CID: 44289364

Max Phase: Preclinical

Molecular Formula: C20H34O2

Molecular Weight: 306.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(O)CC[C@H]2[C@@H]3CC[C@H]4CC(O)CC[C@]4(C)[C@H]3CC[C@@]21C

Standard InChI:  InChI=1S/C20H34O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h13-17,21-22H,4-12H2,1-3H3/t13-,14?,15+,16-,17-,18-,19-,20?/m0/s1

Standard InChI Key:  QGKQXZFZOIQFBI-KAPVAOFQSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  1  0  0  0  0  0999 V2000
    6.3792   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -3.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -3.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5667   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3375   -0.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -3.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500   -4.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -2.2417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -3.4042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -3.4000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -4.4917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  9  1  0
  4  1  1  0
  5  4  1  0
  6  2  1  0
  7  1  1  0
  8  1  1  0
  9  8  1  0
 10  2  1  0
 11  4  1  0
 12  5  1  0
 13 12  1  0
 14  7  1  0
 15  6  1  0
 16  7  1  0
 17 10  1  0
 18 17  1  0
  2 19  1  1
  1 20  1  1
 21 18  1  0
 22  7  1  0
  5 23  1  1
  3 24  1  6
  4 25  1  6
  6 26  1  6
 14 11  1  0
  3  5  1  0
  6 13  1  0
 15 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA40294

   ANDROSTANE

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: 306.49

Molecular Weight (Monoisotopic): 306.2559

AlogP: 4.14

#Rotatable Bonds: ┄

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: 3.48

CX LogD: 3.48

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.71

Np Likeness Score: 2.37

References

1. Smith PA, Sorich MJ, McKinnon RA, Miners JO..  (2003)  Pharmacophore and quantitative structure-activity relationship modeling: complementary approaches for the rationalization and prediction of UDP-glucuronosyltransferase 1A4 substrate selectivity.,  46  (9): [PMID:12699380] [10.1021/jm020397c]

Source

Source(1):

• Scientific Literature