Androstenediol (BioCAD00000006570)

feces adipose tissue adrenal cortex prostate skeletal muscle testis

Metabolite Card

Formula: C19H30O2 (290.2246)
SMILES: [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

Synonyms [en]

Androstenediol; 5-Androstenediol; Androst-5-ene-3beta,17beta-diol; Hermaphrodiol; androst-5-en-3beta,17beta-diol; 3beta,17beta-Dihydroxyandrost-5-ene

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Androstenediol. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000006570). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

5-Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, dehydroepiandrosterone (DHEA). 5-Androstenediol is less androgenic than 4-androstenediol, and stimulates the immune system. When administered to rats in vivo, 5-androstenediol has approximately 1/70 the androgenicity of DHEA, 1/185 the androgenicity of androstenedione, and 1/475 the androgenicity of testosterone (Wikipedia). Because it induces production of white blood cells and platelets, 5-androstenediol is being developed as a radiation countermeasure as Neumune (HE2100). An intermediate in testosterone biosynthesis, found in the testis or the adrenal glands. 5-Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-hydroxysteroid dehydrogenases), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-fydroxysteroid dehydrogenase).

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 16895-59-3
  • CAS Registry Number: 19793-20-5
  • CAS Registry Number: 521-17-5
  • PubChem: 10634
  • PubChem: 13215813
  • PubChem: 44135378
  • ChEBI: ChEBI:2710
  • HMDB: HMDB0003818
  • LipidMaps: LMST02020005
  • KEGG: C04295
  • BioCyc: CPD-23957
  • NCBI MeSH: Androstenediol
  • Wikipedia: Androstenediol
  • DrugBank: DB01524
  • RefMet: RM0126044
  • MoNA: HMDB0003818_c_ms_2049
  • MoNA: NGA00361
  • MoNA: NGA00362
  • MoNA: NGA00363
  • MoNA: NGA00364
  • Metlin: METLIN_41835
  • Coconut NaturalProduct: CNP0294937.1
  • Coconut NaturalProduct: CNP0294937.3
  • Coconut NaturalProduct: CNP0294937.4
  • Coconut NaturalProduct: CNP0294937.7
  • Coconut NaturalProduct: CNP0327082.1
  • Coconut NaturalProduct: CNP0592534.1
  • Coconut NaturalProduct: CNP0592534.2
  • Coconut NaturalProduct: CNP0592534.3
  • Coconut NaturalProduct: CNP0592534.4
  • Coconut NaturalProduct: CNP0606283.1
  • Coconut NaturalProduct: CNP0606283.2
  • Coconut NaturalProduct: CNP0606283.3
  • Coconut NaturalProduct: CNP0606283.4

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02499 1.1.1.145 testosterone delta5-delat4-isomerase;
KEGG:R03406 1.1.1.51 androst-5-ene-3beta,17beta-diol:NAD+ oxidoreductase
KEGG:R03407 1.1.1.51 androst-5-ene-3beta,17beta-diol:NADP+ oxidoreductase
Rhea:RHEA:46205 androst-5-en-3β,17β-diol + reduced [NADPH—hemoprotein reductase] + O2 => androst-5-en-3β,7α,17β-triol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:46206 androst-5-en-3β,7α,17β-triol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => androst-5-en-3β,17β-diol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:46207 androst-5-en-3β,17β-diol + reduced [NADPH—hemoprotein reductase] + O2 <=> androst-5-en-3β,7α,17β-triol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:46221 androst-5-en-3β,17β-diol + NAD+ => 3β-hydroxyandrost-5-en-17-one + NADH + H+
Rhea:RHEA:46222 3β-hydroxyandrost-5-en-17-one + NADH + H+ => androst-5-en-3β,17β-diol + NAD+
Rhea:RHEA:46223 androst-5-en-3β,17β-diol + NAD+ <=> 3β-hydroxyandrost-5-en-17-one + NADH + H+
Rhea:RHEA:46629 3β-hydroxyandrost-5-en-17-one + NADPH + H+ => androst-5-en-3β,17β-diol + NADP+
Rhea:RHEA:46630 androst-5-en-3β,17β-diol + NADP+ => 3β-hydroxyandrost-5-en-17-one + NADPH + H+
Rhea:RHEA:46631 3β-hydroxyandrost-5-en-17-one + NADPH + H+ <=> androst-5-en-3β,17β-diol + NADP+
Rhea:RHEA:56933 androst-5-en-3β,17β-diol + NAD+ => 17β-hydroxy-androst-5-en-3-one + NADH + H+
Rhea:RHEA:56934 17β-hydroxy-androst-5-en-3-one + NADH + H+ => androst-5-en-3β,17β-diol + NAD+
Rhea:RHEA:56935 androst-5-en-3β,17β-diol + NAD+ <=> 17β-hydroxy-androst-5-en-3-one + NADH + H+
BioCyc:RXN-21988 1.1.1.145 CPD-23957 + NAD --> CPD-23979 + NADH + PROTON
BioCyc:RXN-21977 1.1.1.64 3-BETA-HYDROXYANDROST-5-EN-17-ONE + NADPH + PROTON --> CPD-23957 + NADP
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