13-epiestradiol

ID: ALA3526277

Chembl Id: CHEMBL3526277

PubChem CID: 7004689

Max Phase: Preclinical

Molecular Formula: C18H24O2

Molecular Weight: 272.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O

Standard InChI:  InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18-/m1/s1

Standard InChI Key:  VOXZDWNPVJITMN-DFBDCSAJSA-N

Alternative Forms

1. Parent:

   

   ALA3526277

   (8R,9S,13R,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol

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: 272.39

Molecular Weight (Monoisotopic): 272.1776

AlogP: 3.61

#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: 10.33

CX Basic pKa: ┄

CX LogP: 3.75

CX LogD: 3.74

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.76

Np Likeness Score: 2.24

References

1. Sneitz N, Vahermo M, Mosorin J, Laakkonen L, Poirier D, Finel M..  (2013)  Regiospecificity and stereospecificity of human UDP-glucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiol.,  41  (3): [PMID:23288867] [10.1124/dmd.112.049072]

2. Cortés-Benítez F, Roy J, Maltais R, Poirier D..  (2017)  Impact of androstane A- and D-ring inversion on 17β-hydroxysteroid dehydrogenase type 3 inhibitory activity, androgenic effect and metabolic stability.,  25  (7): [PMID:28254377] [10.1016/j.bmc.2017.02.008]

Source

Source(1):

• Scientific Literature