(16R,17S)-13-Methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,16,17-triol

ID: ALA1232445

Chembl Id: CHEMBL1232445

Cas Number: 1228-72-4

PubChem CID: 256737

Product Number: E137449

Max Phase: Preclinical

Molecular Formula: C18H24O3

Molecular Weight: 288.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 17-Epiestriol | 17-Epiestriol|1228-72-4|17alpha-Estriol|UNII-4G7IHY560Z|4G7IHY560Z|16alpha,17alpha-estriol|(8R,9S,13S,14S,16R,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol|16alpha-Hydroxy-17alpha-estradiol|NSC 84051|NSC-84051|(16alpha,17alpha)-Estra-1,3,5(10)-Triene-3,16,17-Triol|Estra-1,3,5(10)-triene-3,16,17-triol, (16alpha,17alpha)-|1,3,5(10)-Estratriene-3,16alpha,17alpha-triol|3,16alpha,17alpha-Trihydroxy-1,3,5(10)-estratriene|Estra-1,3,5(10)-trienShow More⌵

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

Standard InChI:  InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17-,18+/m1/s1

Standard InChI Key:  PROQIPRRNZUXQM-PNVOZDDCSA-N

Alternative Forms

1. Parent:

   

   ALA1232445

   17-Epiestriol

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: 288.39

Molecular Weight (Monoisotopic): 288.1725

AlogP: 2.58

#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: 10.33

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: 2.51

References

1. Azzaoui K, Diaz-Perez MJ, Zannis-Hadjoupoulos M, Price GB, Wainer IW..  (1998)  Effect of steroids on DNA synthesis in an in vitro replication system: initial quantitative structure-activity relationship studies and construction of a non-estrogen receptor pharmacophore.,  41  (9): [PMID:9554872] [10.1021/jm970725m]

2. Good AC, So SS, Richards WG..  (1993)  Structure-activity relationships from molecular similarity matrices.,  36  (4): [PMID:8474098] [10.1021/jm00056a002]

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

4. 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]

Source

Source(1):

• Scientific Literature