ID: ALA335062

Max Phase: Preclinical

Molecular Formula: C19H32O2

Molecular Weight: 292.46

Molecule Type: Small molecule

Representations

Synonyms (1): Androstandiol
Synonyms from Alternative Forms(1):

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-KHOSGYARSA-N

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

Properties

Molecular Weight: 292.46

Molecular Weight (Monoisotopic): 292.2402

AlogP: 3.75

#Rotatable Bonds: 0

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.20

CX LogD: 3.20

Aromatic Rings: 0

Heavy Atoms: 21

QED Weighted: 0.71

Np Likeness Score: 2.37

References

1. 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]

2. Anderson A, Boyd AC, Clark JK, Fielding L, Gemmell DK, Hamilton NM, Maidment MS, May V, McGuire R, McPhail P, Sansbury FH, Sundaram H, Taylor R..  (2000)  Conformationally constrained anesthetic steroids that modulate GABA(A) receptors.,  43  (22): [PMID:11063608] [10.1021/jm000977e]

3. Cherkasov A, Ban F, Santos-Filho O, Thorsteinson N, Fallahi M, Hammond GL..  (2008)  An updated steroid benchmark set and its application in the discovery of novel nanomolar ligands of sex hormone-binding globulin.,  51  (7): [PMID:18330978] [10.1021/jm7011485]

4. Sato H, Macchiarulo A, Thomas C, Gioiello A, Une M, Hofmann AF, Saladin R, Schoonjans K, Pellicciari R, Auwerx J..  (2008)  Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.,  51  (6): [PMID:18307294] [10.1021/jm7015864]

5. Alvarez-Ginarte YM, Crespo-Otero R, Marrero-Ponce Y, Noheda-Marin P, Garcia de la Vega JM, Montero-Cabrera LA, Ruiz García JA, Caldera-Luzardo JA, Alvarado YJ..  (2008)  Chemometric and chemoinformatic analyses of anabolic and androgenic activities of testosterone and dihydrotestosterone analogues.,  16  (12): [PMID:18514531] [10.1016/j.bmc.2008.04.001]

6. 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]

7. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

8. PubChem BioAssay data set, 

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

10. Ayan D, Maltais R, Hospital A, Poirier D..  (2014)  Chemical synthesis, cytotoxicity, selectivity and bioavailability of 5α-androstane-3α,17β-diol derivatives.,  22  (21): [PMID:25300820] [10.1016/j.bmc.2014.09.026]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays