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
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.
DBLinks
- CAS Registry Number: 68-96-2
- PubChem CID: 6238
- ChEBI: 17252
- HMDB: HMDB0000374
- LipidMaps: LMST02030161
- KEGG: C01176
- BioCyc: 17-ALPHA-HYDROXYPROGESTERONE
- NCBI MeSH: 17-alpha-Hydroxyprogesterone
- Wikipedia: Hydroxyprogesterone
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
- WishartLab ClassyFire: [Pregnane steroids] Pregnane steroids
- RefMet: [C21 steroids] C21 steroids
- LipidMaps: [C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]] C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
- ChEBI: [CHEBI:17252] 17alpha-hydroxyprogesterone
- Coconut NaturalProduct: [Pregnane steroids] Pregnane steroids
| 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 |
Taxonomy Source
- Homo sapiens [ncbi taxid: 9606]
- Linum usitatissimum [ncbi taxid: 4006]
- 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 |