Dihydrotestosterone (BioCAD00000010092)

blood cerebrospinal fluid (csf) urine adipose tissue adrenal cortex adrenal gland epidermis fibroblasts hair kidney liver neuron ovary prostate skeletal muscle testis thyroid gland

Metabolite Card

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

Synonyms [en]

Androstanolone; dihydrotestosterone; Stanolone; 17beta-Hydroxyandrostan-3-one; 17beta-Hydroxy-5alpha-androstan-3-one; 5alpha-Dihydrotestosterone

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Dihydrotestosterone. 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: BioCAD00000010092). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Dihydrotestosterone is a potent androgenic metabolite of testosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid. -- Pubchem; Dihydrotestosterone (DHT) (INN: androstanolone) is a biologically active metabolite of the hormone testosterone, formed primarily in the prostate gland, testes, hair follicles, and adrenal glands by the enzyme 5-alpha-reductase by means of reducing the alpha 4,5 double-bond. Dihydrotestosterone belongs to the class of compounds called androgens, also commonly called androgenic hormones or testoids. DHT is thought to be approximately 30 times more potent than testosterone because of increased affinity to the androgen receptor.

Cytoplasm Extracellular Membrane Endoplasmic reticulum
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 521-18-6
  • CAS Registry Number: 521-18-6 (free)
  • CAS Registry Number: 571-24-4
  • PubChem: 10635
  • PubChem: 11302
  • PubChem: 44403751
  • ChEBI: ChEBI:16330
  • ChEBI: ChEBI:2150
  • HMDB: HMDB0002961
  • HMDB: HMDB0006770
  • LipidMaps: LMST02020042
  • LipidMaps: LMST02020069
  • KEGG: C03917
  • KEGG: D07456
  • BioCyc: 17-BETA-HYDROXY-5ALPHA-ANDROSTAN-3-O
  • NCBI MeSH: Dihydrotestosterone
  • Wikipedia: Dihydrotestosterone
  • DrugBank: DB02901
  • RefMet: RM0018333
  • RefMet: RM0125914
  • MoNA: AU280501
  • MoNA: AU280502
  • MoNA: AU280503
  • MoNA: AU280504
  • MoNA: AU280505
  • MoNA: AU280506
  • MoNA: FFF00207
  • MoNA: FFF00208
  • MoNA: FFF00209
  • MoNA: FFF00210
  • MoNA: FFF00211
  • MoNA: FFF00212
  • MoNA: FFF00213
  • MoNA: FFF00214
  • MoNA: FFF00215
  • MoNA: FFF00216
  • MoNA: FFF00217
  • MoNA: FFF00218
  • MoNA: FFF00219
  • MoNA: FFF00220
  • MoNA: FFF00221
  • MoNA: FFF00222
  • MoNA: FFF00223
  • MoNA: FFF00224
  • MoNA: FFF00225
  • MoNA: FFF00226
  • MoNA: FFF00227
  • MoNA: FFF00228
  • MoNA: FFF00229
  • MoNA: FFF00230
  • MoNA: FFF00231
  • MoNA: HMDB0002961_c_ms_99791
  • MoNA: HMDB0002961_c_ms_99792
  • MoNA: JP004114
  • Metlin: METLIN_2789
  • Coconut NaturalProduct: CNP0117289.1
  • Coconut NaturalProduct: CNP0117289.5

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02497 1.3.1.22 dihydrotestosterone:NADP+ delta4-oxidoreductase
KEGG:R04330 1.1.1.53 androstan-3alpha,17beta-diol:NAD+ oxidoreductase
KEGG:R04344 1.1.1.210 3beta-hydroxysteroid:NADP+ oxidoreductase
KEGG:R08963 1.1.1.50 androstan-3alpha,17beta-diol:NADP+ oxidoreductase
KEGG:R13220 1.1.1.51 dihydrotestosterone:NADP+ 17-oxidoreductase
KEGG:R13221 1.1.1.51 dihydrotestosterone:NAD+ 17-oxidoreductase
Rhea:RHEA:16298 1.1.1.210 5α-androstane-3β,17β-diol + NADP+ => 17β-hydroxy-5α-androstan-3-one + NADPH + H+
Rhea:RHEA:16299 1.1.1.210 17β-hydroxy-5α-androstan-3-one + NADPH + H+ => 5α-androstane-3β,17β-diol + NADP+
Rhea:RHEA:16300 1.1.1.210 5α-androstane-3β,17β-diol + NADP+ <=> 17β-hydroxy-5α-androstan-3-one + NADPH + H+
Rhea:RHEA:41993 17β-hydroxy-5α-androstan-3-one + NAD+ => 5α-androstan-3,17-dione + NADH + H+
Rhea:RHEA:41994 5α-androstan-3,17-dione + NADH + H+ => 17β-hydroxy-5α-androstan-3-one + NAD+
Rhea:RHEA:41995 17β-hydroxy-5α-androstan-3-one + NAD+ <=> 5α-androstan-3,17-dione + NADH + H+
Rhea:RHEA:42005 1.1.1.53 5α-androstane-3α,17β-diol + NAD+ => 17β-hydroxy-5α-androstan-3-one + NADH + H+
Rhea:RHEA:42006 1.1.1.53 17β-hydroxy-5α-androstan-3-one + NADH + H+ => 5α-androstane-3α,17β-diol + NAD+
Rhea:RHEA:42007 1.1.1.53 5α-androstane-3α,17β-diol + NAD+ <=> 17β-hydroxy-5α-androstan-3-one + NADH + H+
Rhea:RHEA:42117 5α-androstane-3α,17β-diol + NADP+ => 17β-hydroxy-5α-androstan-3-one + NADPH + H+
Rhea:RHEA:42118 17β-hydroxy-5α-androstan-3-one + NADPH + H+ => 5α-androstane-3α,17β-diol + NADP+
Rhea:RHEA:42119 5α-androstane-3α,17β-diol + NADP+ <=> 17β-hydroxy-5α-androstan-3-one + NADPH + H+
Rhea:RHEA:42121 17β-hydroxy-5α-androstan-3-one + NADP+ => 5α-androstan-3,17-dione + NADPH + H+
Rhea:RHEA:42122 5α-androstan-3,17-dione + NADPH + H+ => 17β-hydroxy-5α-androstan-3-one + NADP+
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Organism Source

Taxonomy Source

  1. Penis cervi [ncbi taxid: ]

Pathway Synthetic

pathway id name
BioCyc:HUMAN_PWY66-378 androgen biosynthesis
BioCyc:META_PWY66-378 androgen biosynthesis
BioCyc:META_PWY-6944 androstenedione degradation
BioCyc:MTBH37RV_PWY-6947 superpathway of cholesterol degradation II (cholesterol dehydrogenase)
BioCyc:META_PWY-6947 superpathway of cholesterol degradation II (cholesterol dehydrogenase)
BioCyc:MTBH37RV_PWY-6944 androstenedione degradation
BioCyc:THAPS_PWY66-378 androgen biosynthesis
Reactome:R-BTA-1430728 Metabolism
Reactome:R-BTA-556833 Metabolism of lipids
Reactome:R-CFA-1430728 Metabolism
Reactome:R-CFA-556833 Metabolism of lipids
Reactome:R-DRE-196071 Metabolism of steroid hormones
Reactome:R-DRE-193048 Androgen biosynthesis
Reactome:R-DDI-193048 Androgen biosynthesis
Reactome:R-MMU-1430728 Metabolism
Reactome:R-MMU-556833 Metabolism of lipids
Reactome:R-MMU-8957322 Metabolism of steroids
Reactome:R-PFA-193048 Androgen biosynthesis
Reactome:R-RNO-196071 Metabolism of steroid hormones
Reactome:R-RNO-193048 Androgen biosynthesis
View All Pathways