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Chemistry

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Also known as: Etiocholan-17.beta.-ol-3-one, Anaprotin, 5.beta.,17.beta.-hydroxyandrostan-3-one, 5.beta.-androstan-3-one, 17.beta.-hydroxy-, 5.beta.-dihydrotestosterone, 5b-dihydrotestosterone

Molecular Formula

C₁₉H₃₀O₂

Molecular Weight

290.4 g/mol

InChI Key

NVKAWKQGWWIWPM-UHFFFAOYSA-N

A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.

1 2D Structure

Androstan-17B-Ol-3-One

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

2.1.2 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/h12,14-17,21H,3-11H2,1-2H3

2.1.3 InChI Key

NVKAWKQGWWIWPM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC12CCC(=O)CC1CCC3C2CCC4(C3CCC4O)C

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 17 Beta Hydroxy 5 Beta Androstan 3 One

2. 17 Beta-hydroxy-5 Beta-androstan-3-one

3. 17beta Hydroxy 5alpha Androstan 3 One

4. 17beta-hydroxy-5alpha-androstan-3-one

5. 5 Alpha Dht

6. 5 Alpha Dihydrotestosterone

7. 5 Alpha-dihydrotestosterone

8. 5 Beta Dihydrotestosterone

9. 5 Beta-dihydrotestosterone

10. 5-alpha Dihydrotestosterone

11. 5-alpha-dht

12. Anaprotin

13. Andractim

14. Androstanolone

15. Beta-hydroxy-5 Beta-androstan-3-one, 17

16. Dihydroepitestosterone

17. Dihydrotestosterone

18. Dihydrotestosterone, 5-alpha

19. Gelovit

20. Stanolone

2.2.2 Depositor-Supplied Synonyms

1. Etiocholan-17.beta.-ol-3-one

2. Anaprotin

3. 5.beta.,17.beta.-hydroxyandrostan-3-one

4. 5.beta.-androstan-3-one, 17.beta.-hydroxy-

5. 5.beta.-dihydrotestosterone

6. 5b-dihydrotestosterone

7. 17.beta.-hydroxyetiocholan-3-one

8. Nsc-15460

9. 5.beta.-androstan-17.beta.-ol-3-one

10. Androstan-3-one, 17-hydroxy-, (5.alpha.,17.beta.)-

11. Oprea1_456186

12. Schembl9340073

13. Bcp22808

14. Nsc15460

15. Nsc61692

16. Bbl028114

17. Nsc-61692

18. Stk366316

19. Akos002232213

20. Akos016303784

21. Ncgc00249620-01

22. Vs-08671

23. Ft-0662160

24. Ab00987792-01

25. 1-hydroxy-9a,11a-dimethyl-hexadecahydro-1h-cyclopenta[a]phenanthren-7-one

26. Andractim Pound>> Lg 152 Pound>>lg-152 Pound>> Lg152 Pound>> Stanolone Pound>> Dihydrotestosterone Pound>> Dihydrotestosterone Propionate

2.3 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₃₀O₂
Molecular Weight	290.4 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	290.224580195 g/mol
Monoisotopic Mass	290.224580195 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	459
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	7
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Androgens

Compounds that interact with ANDROGEN RECEPTORS in target tissues to bring about the effects similar to those of TESTOSTERONE. Depending on the target tissues, androgenic effects can be on SEX DIFFERENTIATION; male reproductive organs, SPERMATOGENESIS; secondary male SEX CHARACTERISTICS; LIBIDO; development of muscle mass, strength, and power. (See all compounds classified as Androgens.)

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