CAS 63-05-8|CAS 1963-5-8|4-Androstenedione|4-androstenedione|(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione|4-ANDROSTENE-3-17-DIONE|(8R,9S,10R,13S,14S)...

General Information

Structure

Molecular Formula

C₁₉H₂₆O₂

Molecular Mass

286.40854

Exact Mass

286.19328007

Charge

0

InChI

InChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

InChIKey

AEMFNILZOJDQLW-QAGGRKNESA-N

Canonic Smiles

O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C

Isomeric Smiles

O=C1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)CC3)C)CC2)CC1)C

Calculated Properties

JChem

LogD (pH = 7.4)

3.93

LogD (pH = 5.5)

3.93

Log P

3.93

Rotatable Bonds

0

H Donor

0

H Acceptors

2

Lipinski's Rule of Five

true

Acid pKa

18.52

Polar Surface Area

34.14

Polarizability

33.22

Molar Refractivity

83.61

LOG S

-4.55

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

4-Androstenedione4-ANDROSTENE-3-17-DIONE(8R,9S,10R,13S,14S)-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dioneAndrostenedione4-Androstene-3,17-dione4-雄烯-3,17-二酮雄烯二酮AndrostenedioneSKF 217017-KetotestosteroneFecundinΔ4-Androstene-3,17-dione4-Androstene-3,17-dioneNSC 95633,17-Dioxoandrost-4-ene4-ANDROSTENE-3-17-DIONEandrost-4-ene-3,17-dione4-Androstene-3,17-dioneDelta(4)-androsten-3,17-dioneAndrost-4-ene-3,17-dioneandrost-4-ene-3,17-dioneAndrostenedioneDelta(4)-androstene-3,17-dione

IUPAC Traditional name

4-androstenedione androstenedione

IUPAC name

(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione (1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione (3aS,3bR,9aR,9bS,11aS)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-dione

Names and Identifiers

Registration numbers

PubChem CID

6128

Chemspider ID

5898

PubChem SID

16096478346508011248696818145630

CAS Number

63-05-81963-5-8

CHEBI ID

16422CHEBI:13830CHEBI:20322CHEBI:16422CHEBI:40930CHEBI:11964CHEBI:2709

Wikipedia Title

DrugBank ID

IUPHAR ligand ID

CHEMBL

Unique Ingredient Identifier

EC Number

MDL Number

Beilstein Number

PubMed Citation Links

2442334424740546

MetaboLights Database

MTBLS1906MTBLS3487MTBLS3444MTBLS5148MTBLS3935MTBLS4820MTBLS2633MTBLS1785MTBLS3886MTBLS3854MTBLS2267MTBLS312MTBLS1041MTBLS5132

Rhea Database

RHEA:38199RHEA:47256RHEA:46656RHEA:53228RHEA:19561RHEA:46648RHEA:21628RHEA:50816RHEA:51056RHEA:14753RHEA:51048RHEA:22696RHEA:14929RHEA:14981RHEA:42224RHEA:50812RHEA:45968RHEA:43936RHEA:38195

KNApSAcK Database

C00003644

BRENDA Ligand Database

591348981755941319194521786563055468222627119924441242611868046

Patent number

US2005143366EP1623712US2008014642US2007184429

Protein Data Bank

3nhx5jl71eup7cl93eqm3nuv4jbt6tzd2vcv3s794kq82vct3uzz4xo75jl91xf04qck5jkv5jl63iw11qyx3cas4at26ubq4qdc3nbr6ucy

SABIO-RK Database

191787841260011977793010858957672951308116037729619181450676351915

SureChEMBL Database

SCHEMBL23272

KEGG DRUG Database

D00051

BKMS React Database

124266305592444489846825913226219451755941319711980462178651186

MetaCyc Database

ANDROST4ENE

Golm Database

ec1a738e-76cb-4b62-aa0c-bc8320d55d3ca521bb08-21a2-45bb-8116-127017095b96

SwissLipids Database Link

SLM:000001060

HMDB Database

HMDB0000053

GeneOntology Database

GO:0035941GO:1903449

BindingDB Database

91713

ACToR Database

63-05-8104534-78-3

ArrayExpress (Gene Expression Altlas)

E-GEOD-41405

IntEnz Database

EC 1.14.14.14EC 1.14.14.19EC 1.1.1.51EC 1.1.1.63EC 1.3.99.4EC 1.14.13.54EC 1.14.15.19EC 1.3.99.5EC 1.1.1.64EC 1.14.14.32EC 1.1.1.239EC 1.14.99.12

LIPID MAPS Instance

Gmelin ID

Reaxys Registry

KEGG ID

CompTox Database

PDBeChem Database

Drug Central Database

215

VirtualMetabolicHuman Database

andrstndn

Registration numbers

Properties

Pharmacology Properties

Metabolism

Liver

Legal Status

Schedule III (US)

Gene Information

human ... HSD17B3(3293)

Product Information

Safety Information

Drug Control

USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada

USDEA Schedule IIIN

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS Link

Download link

3

BV8150000

Controlled Substance, -20°C Freezer

Physical Property

Properties

Related Proteins

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB01536

Drug Groups

illicit; experimental

Description

A delta-4 C19 steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. [PubChem]

DB07386

Drug information: experimental

Wikipedia

Androstenedione

Sigma Aldrich

10340

Other Notes
Sales restrictions may apply
Biochem/physiol Actions
Testosterone precursor and metabolite with androgenic activity; may increase the risk of prostate or pancreatic cancer.

46033

Biochem/physiol Actions
Testosterone precursor and metabolite with androgenic activity; may increase the risk of prostate or pancreatic cancer.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

TRC

A637550

Testosterone precursor and metabolite with androgenic activity. Controlled substance (anabolic steroid).

ChEBI

CHEBI:16422

A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.

Molecule Details

References

PubChem Literature

From Data Sources

• Walker, V.R., et al.: Anal. Biopchem., 234, 194 (1996)

• King, D.S., et al.: J. Am. Med. Assoc., 281, 2020 (1996)

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:1323