17alpha-Hydroxyprogesterone (BioCAD00000002066)

blood saliva urine adipose tissue adrenal cortex adrenal gland testis

Metabolite Card

Formula: C21H30O3 (330.2195)
SMILES: [H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Synonyms [en]

17ALPHA-HYDROXYPROGESTERONE; 17-Hydroxyprogesterone; Pregn-4-ene-3,20-dione-17-ol; hydroxyprogesterone; 17alpha-Hydroxy-4-pregnene-3,20-dione; 17alpha-Hydroxy-progesterone

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

17alpha-Hydroxyprogesterone. 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: BioCAD00000002066). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

17-Hydroxyprogesterone also known as 17-OH progesterone (17-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. Formally it is a 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone. 17-Hydroxyprogesterone is found in all vertebrates. It is a chemical intermediate in the biosynthesis of many endogenous steroids, including androgens, estrogens, glucocorticoids, mineralocorticoids and neurosteroids. In particular, 17-Hydroxyprogesterone serves as an intermediate in the biosynthesis of hydrocortisone and gonadal steroid hormones. It is derived from progesterone via the enzyme known as 17-hydroxylase, a cytochrome P450 enzyme also known as CYP17A1. It can also be biosynthesized from 17-hydroxypregnenolone via the enzyme 3beta-hydroxysteroid dehydrogenase/delta5-4 isomerase (PMID: 1955079). 17-OHP is an agonist of the progesterone receptor (PR). It is also an antagonist of the mineralocorticoid receptor (MR) as well as a partial agonist of the glucocorticoid receptor (GR). 17-Hydroxyprogesterone is a natural progestin and in pregnancy it increases in the third trimester primarily due to fetal adrenal production. 17-Hydroxyprogesterone is primarily produced in the adrenal glands and to some degree in the gonads, specifically the corpus luteum of the ovary. Normal levels are 3-90 ng/dl in children, and in women, 15-70 ng/dl prior to ovulation, and 35-290 ng/dl during the luteal phase. Measurements of levels of 17-hydroxyprogesterone are useful in the evaluation of patients with suspected congenital adrenal hyperplasia as the typical enzymes that are defective, namely 21-hydroxylase, lead to a build-up of 17-OHP. 17-OHP levels can also be used to measure contribution of progestational activity of the corpus luteum during pregnancy as progesterone but not 17-OHP is also contributed by the placenta.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 110850-01-6
  • CAS Registry Number: 3168-01-2
  • CAS Registry Number: 604-09-1
  • CAS Registry Number: 68-96-2
  • PubChem: 521928
  • PubChem: 6238
  • ChEBI: ChEBI:17252
  • HMDB: HMDB0000374
  • LipidMaps: LMST02030161
  • KEGG: C01176
  • BioCyc: 17-ALPHA-HYDROXYPROGESTERONE
  • NCBI MeSH: 17-alpha-Hydroxyprogesterone
  • Wikipedia: 17%CE%B1-Hydroxyprogesterone
  • Wikipedia: 17-Hydroxyprogesterone
  • Wikipedia: Hydroxyprogesterone
  • DrugBank: DB14570
  • RefMet: RM0138903
  • MoNA: AU239701
  • MoNA: AU239702
  • MoNA: AU239703
  • MoNA: AU239704
  • MoNA: AU239705
  • MoNA: AU239706
  • MoNA: AU239757
  • MoNA: AU239758
  • MoNA: AU239759
  • MoNA: HMDB0000374_c_ms_2225
  • MoNA: HMDB0000374_ms_ms_588
  • MoNA: HMDB0000374_ms_ms_589
  • MoNA: HMDB0000374_ms_ms_590
  • MoNA: JP005735
  • MoNA: LU114401
  • MoNA: LU114402
  • MoNA: LU114403
  • MoNA: LU114404
  • MoNA: LU114405
  • MoNA: LU114406
  • Metlin: METLIN_3777
  • Metlin: METLIN_41889
  • Metlin: METLIN_44235
  • Coconut NaturalProduct: CNP0001365.0
  • Coconut NaturalProduct: CNP0259281.1
  • Coconut NaturalProduct: CNP0318644.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02211 1.14.14.19 progesterone,NADPH-hemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating)
KEGG:R03325 1.1.1.149 17alpha,20alpha-dihydroxypregn-4-en-3-one:NADP+ 20-oxidoreductase
KEGG:R03326 1.14.14.16 17alpha-hydroxyprogesterone,NADPH-hemoprotein reductase:oxygen oxidoreductase (21-hydroxylating)
KEGG:R03327 1.1.1.145 17alpha-hydroxypregnenolone:NAD+ 3-oxidoreductase
KEGG:R03329 1.14.15.4 steroid,reduced-adrenal-ferredoxin:oxygen oxidoreductase (11-hydroxylating)
KEGG:R08206 1.14.13.54 C01176 + C00005 + C00080 + C00007<=>C00280 + C00033 + C00006 + C00001
KEGG:R08518 1.14.14.32 17alpha-hydroxyprogesterone,NADPH---hemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating, acetate-releasing)
KEGG:R13215 1.3.1.22 5alpha-pregnan-17alpha-ol-3,20-dione:NADP+ Delta4-oxidoreductase
Rhea:RHEA:14754 1.14.14.19 17α-hydroxyprogesterone + reduced [NADPH—hemoprotein reductase] + O2 => androst-4-ene-3,17-dione + acetate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+
Rhea:RHEA:14755 1.14.14.19 androst-4-ene-3,17-dione + acetate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+ => 17α-hydroxyprogesterone + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:14756 1.14.14.19 17α-hydroxyprogesterone + reduced [NADPH—hemoprotein reductase] + O2 <=> androst-4-ene-3,17-dione + acetate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+
Rhea:RHEA:15854 1.1.1.149 (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD+ => 17α-hydroxyprogesterone + NADH + H+
Rhea:RHEA:15855 1.1.1.149 17α-hydroxyprogesterone + NADH + H+ => (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD+
Rhea:RHEA:15856 1.1.1.149 (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD+ <=> 17α-hydroxyprogesterone + NADH + H+
Rhea:RHEA:15858 1.1.1.149 (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NADP+ => 17α-hydroxyprogesterone + NADPH + H+
Rhea:RHEA:15859 1.1.1.149 17α-hydroxyprogesterone + NADPH + H+ => (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NADP+
Rhea:RHEA:15860 1.1.1.149 (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NADP+ <=> 17α-hydroxyprogesterone + NADPH + H+
Rhea:RHEA:21629 1.14.13.54 17α-hydroxyprogesterone + NADPH + O2 => androst-4-ene-3,17-dione + acetate + NADP+ + H2O
Rhea:RHEA:21630 1.14.13.54 androst-4-ene-3,17-dione + acetate + NADP+ + H2O => 17α-hydroxyprogesterone + NADPH + O2
Rhea:RHEA:21631 1.14.13.54 17α-hydroxyprogesterone + NADPH + O2 <=> androst-4-ene-3,17-dione + acetate + NADP+ + H2O
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Organism Source

Taxonomy Source

  1. Homo sapiens [ncbi taxid: 9606]
  2. Linum usitatissimum [ncbi taxid: 4006]
  3. Mus musculus [ncbi taxid: 10090]

Pathway Synthetic

pathway id name
Reactome:R-BTA-1430728 Metabolism
Reactome:R-BTA-556833 Metabolism of lipids
Reactome:R-BTA-194002 Glucocorticoid biosynthesis
Reactome:R-CFA-1430728 Metabolism
Reactome:R-CFA-556833 Metabolism of lipids
Reactome:R-CFA-194002 Glucocorticoid biosynthesis
Reactome:R-DRE-196071 Metabolism of steroid hormones
Reactome:R-DRE-193048 Androgen biosynthesis
Reactome:R-DME-194002 Glucocorticoid biosynthesis
Reactome:R-GGA-194002 Glucocorticoid biosynthesis
Reactome:R-HSA-194002 Glucocorticoid biosynthesis
Reactome:R-HSA-1643685 Disease
Reactome:R-MMU-1430728 Metabolism
Reactome:R-MMU-556833 Metabolism of lipids
Reactome:R-MMU-8957322 Metabolism of steroids
Reactome:R-RNO-196071 Metabolism of steroid hormones
Reactome:R-RNO-193048 Androgen biosynthesis
Reactome:R-SSC-196071 Metabolism of steroid hormones
Reactome:R-SSC-193048 Androgen biosynthesis
Reactome:R-BTA-8957322 Metabolism of steroids
View All Pathways