androst-4-ene-3,17-dione (CHEBI:16422)

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CHEBI:16422 - androst-4-ene-3,17-dione

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ChEBI Name	androst-4-ene-3,17-dione

ChEBI ID	CHEBI:16422

Definition	A 3-oxo Δ⁴-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.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:2709, CHEBI:40930, CHEBI:11964, CHEBI:20322, CHEBI:13830

Supplier Information	ChemicalBook:CB8365581, eMolecules:477820, ZINC000004428526

Download	Molfile XML SDF

more structures >>

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1.7073 1.9445 -0.9202 C 0 0 2 0 0 0 0 0 0 0 0 0

3.4469 0.3915 -0.2043 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0083 -2.2217 1.6214 C 0 0 0 0 0 0 0 0 0 0 0 0

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-2.0106 0.2265 1.8332 C 0 0 0 0 0 0 0 0 0 0 0 0

0.3780 1.9973 -1.7395 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9520 2.2225 -1.6177 C 0 0 0 0 0 0 0 0 0 0 0 0

1.6383 2.9698 0.2681 C 0 0 0 0 0 0 0 0 0 0 0 0

4.0700 1.4233 -1.1728 C 0 0 0 0 0 0 0 0 0 0 0 0

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2.0751 -1.7371 1.2325 H 0 0 0 0 0 0 0 0 0 0 0 0

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3.8858 -0.6010 -0.3413 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5919 0.6857 0.8389 H 0 0 0 0 0 0 0 0 0 0 0 0

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0.2704 -3.2720 1.7938 H 0 0 0 0 0 0 0 0 0 0 0 0

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5 12 1 0 0 0 0

6 13 1 0 0 0 0

7 14 1 0 0 0 0

7 15 1 0 0 0 0

8 16 1 0 0 0 0

10 17 2 0 0 0 0

11 18 1 0 0 0 0

14 19 2 0 0 0 0

17 20 1 0 0 0 0

20 21 2 0 0 0 0

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14 16 1 0 0 0 0

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15 42 1 0 0 0 0

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18 47 1 0 0 0 0

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reading 47 atoms

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47 atoms created

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Wikipedia	License
Androstenedione, or 4-androstenedione (abbreviated as A4 or Δ4-dione), also known as androst-4-ene-3,17-dione, is an endogenous weak androgen steroid hormone and intermediate in the biosynthesis of estrone and of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenediol (androst-5-ene-3β,17β-diol).
Read full article at Wikipedia

Formula

C19H26O2

Net Charge

Average Mass

286.40850

Monoisotopic Mass

286.19328

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

SMILES

[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(=O)CC[C@@]21[H]

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Daphnia magna (NCBI:txid35525)	See: Changes in the Metabolic Elimination Profile of Testosterone Following Exposure of the Crustacean Daphnia magna to TributyltinGerald A. LeBlanc and James B. McLachlanEcotoxicology and Environmental Safety 45, 296-303 (2000)
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	androgen A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors. Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	androst-4-ene-3,17-dione (CHEBI:16422) has role Daphnia magna metabolite (CHEBI:83056) androst-4-ene-3,17-dione (CHEBI:16422) has role androgen (CHEBI:50113) androst-4-ene-3,17-dione (CHEBI:16422) has role human metabolite (CHEBI:77746) androst-4-ene-3,17-dione (CHEBI:16422) has role mouse metabolite (CHEBI:75771) androst-4-ene-3,17-dione (CHEBI:16422) is a 17-oxo steroid (CHEBI:19168) androst-4-ene-3,17-dione (CHEBI:16422) is a 3-oxo-Δ⁴ steroid (CHEBI:47909) androst-4-ene-3,17-dione (CHEBI:16422) is a androstanoid (CHEBI:50402)

Incoming	1α-hydroxyandrost-4-ene-3,17-dione (CHEBI:133778) has functional parent androst-4-ene-3,17-dione (CHEBI:16422) 15α-hydroxyandrost-4-ene-3,17-dione (CHEBI:232766) has functional parent androst-4-ene-3,17-dione (CHEBI:16422) 3,17-dioxoandrost-4-en-19-al (CHEBI:799) has functional parent androst-4-ene-3,17-dione (CHEBI:16422) 6β-hydroxyandrost-4-ene-3,17-dione (CHEBI:87571) has functional parent androst-4-ene-3,17-dione (CHEBI:16422) 9α-hydroxyandrost-4-en-3,17-dione (CHEBI:85549) has functional parent androst-4-ene-3,17-dione (CHEBI:16422)

IUPAC Name

androst-4-ene-3,17-dione

Synonyms	Sources
4-Androstene-3,17-dione	KEGG COMPOUND
4-ANDROSTENE-3-17-DIONE	PDBeChem
Androst-4-ene-3,17-dione	KEGG COMPOUND
androst-4-ene-3,17-dione	UniProt
Androst-4-ene-3,17-dione	KEGG COMPOUND
Androstenedione	KEGG COMPOUND
Δ⁴-androsten-3,17-dione	NIST Chemistry WebBook
Δ⁴-androstene-3,17-dione	ChemIDplus

Manual Xrefs	Databases
215	DrugCentral
ANDROST4ENE	MetaCyc
Androstenedione	Wikipedia
ASD	PDBeChem
C00003644	KNApSAcK
C00280	KEGG COMPOUND
D00051	KEGG DRUG
DB01536	DrugBank
HMDB0000053	HMDB
LMST02020007	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
2059239	Reaxys Registry Number	Reaxys
63-05-8	CAS Registry Number	ChemIDplus
63-05-8	CAS Registry Number	NIST Chemistry WebBook
961672	Gmelin Registry Number	Gmelin

Citations

Ott J, Mayerhofer K, Nouri K, Walch K, Seemann R, Kurz C (2014)
Perioperative androstenedione kinetics in women undergoing laparoscopic ovarian drilling: a prospective study.
Endocrine 47, 936-942 [PubMed:24740546]
[show Abstract]

O'Reilly MW, Taylor AE, Crabtree NJ, Hughes BA, Capper F, Crowley RK, Stewart PM, Tomlinson JW, Arlt W (2014)
Hyperandrogenemia predicts metabolic phenotype in polycystic ovary syndrome: the utility of serum androstenedione.
The Journal of clinical endocrinology and metabolism 99, 1027-1036 [PubMed:24423344]
[show Abstract]

Last Modified

25 October 2018

ChEBI

CHEBI:16422 - androst-4-ene-3,17-dione

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