10,13-Dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA440283

Chembl Id: CHEMBL440283

Cas Number: 521-17-5

PubChem CID: 10634

Max Phase: Unknown

Molecular Formula: C19H30O2

Molecular Weight: 290.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Androstenediol | Androstenediol|Hermaphrodiol|5-Androstenediol|521-17-5|Androst-5-enediol|Neumune|Androst-5-ene-3beta,17beta-diol|3beta,17beta-Dihydroxyandrost-5-ene|Androstenediol [JAN]|delta(sup 5)-Androstenediol|HE2100|Adiol|5-andendiol|(3beta,17beta)-androst-5-ene-3,17-diol|3beta,17beta-Dihydroxy-5-androstene|androst-5-en-3beta,17beta-diol|95PS51EMXY|CHEBI:2710|CHEMBL440283|(3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dShow More⌵

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@@H]2O

Standard InChI:  InChI=1S/C19H30O2/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/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

Standard InChI Key:  QADHLRWLCPCEKT-LOVVWNRFSA-N

Alternative Forms

1. Parent:

   

   ALA440283

   ANDROSTENEDIOL

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 290.45

Molecular Weight (Monoisotopic): 290.2246

AlogP: 3.67

#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: 2.80

CX LogD: 2.80

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.67

Np Likeness Score: 2.79

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. 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]

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

10. Lill MA, Winiger F, Vedani A, Ernst B..  (2005)  Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.,  48  (18): [PMID:16134935] [10.1021/jm050403f]

11. Blizzard TA, Gude C, Morgan JD, Chan W, Birzin ET, Mojena M, Tudela C, Chen F, Knecht K, Su Q, Kraker B, Mosley RT, Holmes MA, Sharma N, Fitzgerald PM, Rohrer SP, Hammond ML..  (2006)  Androstenediol analogs as ER-beta-selective SERMs.,  16  (4): [PMID:16309907] [10.1016/j.bmcl.2005.11.014]

12. Blizzard TA, Gude C, Morgan JD, Chan W, Birzin ET, Mojena M, Tudela C, Chen F, Knecht K, Su Q, Kraker B, Mosley RT, Holmes MA, Rohrer SP, Hammond ML..  (2007)  Androstene-3,5-dienes as ER-beta selective SERMs.,  17  (22): [PMID:17890084] [10.1016/j.bmcl.2007.09.001]

13. 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]

14. Calogeropoulou T, Avlonitis N, Minas V, Alexi X, Pantzou A, Charalampopoulos I, Zervou M, Vergou V, Katsanou ES, Lazaridis I, Alexis MN, Gravanis A..  (2009)  Novel dehydroepiandrosterone derivatives with antiapoptotic, neuroprotective activity.,  52  (21): [PMID:19845386] [10.1021/jm900468p]

15. 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]

16. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

17. PubChem BioAssay data set, 

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

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

20. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

21. PubChem BioAssay data set, 

22. PubChem BioAssay data set, 

23. Ohgane K, Karaki F, Noguchi-Yachide T, Dodo K, Hashimoto Y..  (2014)  Structure-activity relationships of oxysterol-derived pharmacological chaperones for Niemann-Pick type C1 protein.,  24  (15): [PMID:24928400] [10.1016/j.bmcl.2014.05.064]

24. Domínguez-Díaz LR, Eugenia Ochoa M, Soto-Castro D, Farfán N, Morales-Chamorro M, Yépez-Mulia L, Pérez-Campos E, Santillan R, Moreno-Rodríguez A..  (2021)  In vitro, ex vivo and in vivo short-term screening of DHEA nitrate derivatives activity over Trypanosoma cruzi Ninoa and TH strains from Oaxaca State, México.,  48  [PMID:34571489] [10.1016/j.bmc.2021.116417]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names