8,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA316048

Chembl Id: CHEMBL316048

Cas Number: 571-20-0

PubChem CID: 242332

Max Phase: Preclinical

Molecular Formula: C19H32O2

Molecular Weight: 292.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: androstanediol | 571-20-0|3beta-androstanediol|5alpha-Androstane-3beta,17beta-diol|5alpha-Androstan-3beta,17beta-diol|3beta androstanediol|3beta,17beta-Dihydroxy-5alpha-androstane|CHEBI:18329|3.beta.,17.beta.-Androstanediol|(3beta,5alpha,17beta)-androstane-3,17-diol|5-ALPHA-ANDROSTANE-3-BETA,17BETA-DIOL|Androstanediol|5.alpha.-Androstane-3.beta.,17.beta.-diol|3.beta.,17.beta.-Dihydroxy-5.alpha.-androstane|6J0K4253QD|NSC-50891|Androstane-3,17-diol #|Androstane-3,17-diol, (3.beta.,5.alpha.,17.betShow More⌵

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

Standard InChI:  InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1

Standard InChI Key:  CBMYJHIOYJEBSB-YSZCXEEOSA-N

Alternative Forms

1. Parent:

   

   ALA316048

   ANDROSTANEDIOL

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: 292.46

Molecular Weight (Monoisotopic): 292.2402

AlogP: 3.75

#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: 3.20

CX LogD: 3.20

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.71

Np Likeness Score: 2.37

References

1. Stiefl N, Baumann K..  (2003)  Mapping property distributions of molecular surfaces: algorithm and evaluation of a novel 3D quantitative structure-activity relationship technique.,  46  (8): [PMID:12672239] [10.1021/jm021077w]

2. Silverman BD, Platt DE..  (1996)  Comparative molecular moment analysis (CoMMA): 3D-QSAR without molecular superposition.,  39  (11): [PMID:8667357] [10.1021/jm950589q]

3. Jain AN, Koile K, Chapman D..  (1994)  Compass: predicting biological activities from molecular surface properties. Performance comparisons on a steroid benchmark.,  37  (15): [PMID:8057280] [10.1021/jm00041a010]

4. Kubinyi H, Hamprecht FA, Mietzner T..  (1998)  Three-dimensional quantitative similarity-activity relationships (3D QSiAR) from SEAL similarity matrices.,  41  (14): [PMID:9651159] [10.1021/jm970732a]

5. Kotani T, Higashiura K..  (2004)  Comparative molecular active site analysis (CoMASA). 1. An approach to rapid evaluation of 3D QSAR.,  47  (11): [PMID:15139751] [10.1021/jm030364c]

6. Crippen GM..  (1997)  Validation of EGSITE2, a mixed integer program for deducing objective site models for experimental binding data.,  40  (20): [PMID:9379435] [10.1021/jm970211n]

7. Pastor M, Cruciani G, McLay I, Pickett S, Clementi S..  (2000)  GRid-INdependent descriptors (GRIND): a novel class of alignment-independent three-dimensional molecular descriptors.,  43  (17): [PMID:10966742] [10.1021/jm000941m]

8. Wiese TE, Polin LA, Palomino E, Brooks SC..  (1997)  Induction of the estrogen specific mitogenic response of MCF-7 cells by selected analogues of estradiol-17 beta: a 3D QSAR study.,  40  (22): [PMID:9357533] [10.1021/jm9703294]

9. So SS, Karplus M..  (1997)  Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks. 1. Method and validations.,  40  (26): [PMID:9435904] [10.1021/jm970487v]

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

11. Bellavance E, Luu-The V, Poirier D..  (2009)  Potent and selective steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 7, an enzyme that catalyzes the reduction of the key hormones estrone and dihydrotestosterone.,  52  (23): [PMID:19772289] [10.1021/jm900921c]

12. PubChem BioAssay data set, 

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

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

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

16. Kiang TK, Ensom MH, Chang TK..  (2005)  UDP-glucuronosyltransferases and clinical drug-drug interactions.,  106  (1): [PMID:15781124] [10.1016/j.pharmthera.2004.10.013]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays