MiMeDB: Showing metabocard for 17-Hydroxyprogesterone (MMDBc0047909)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:14:28 UTC

Update Date

2024-10-09 20:34:23 UTC

Metabolite ID

MMDBc0047909

Metabolite Identification

Common Name

17-Hydroxyprogesterone

Description

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
17-Hydroxypregn-4-en-3,20-dione	ChEBI
17alpha-Hydroxy-4-pregnene-3,20-dione	ChEBI
17alpha-Hydroxy-progesterone	ChEBI
delta(4)-Pregnene-17alpha-ol-3,20-dione	ChEBI
Hidroxiprogesterona	ChEBI
Hydroxyprogesterone	ChEBI
Hydroxyprogesteronum	ChEBI
Pregn-4-ene-3,20-dione-17-ol	ChEBI
17a-Hydroxy-4-pregnene-3,20-dione	Generator
17Α-hydroxy-4-pregnene-3,20-dione	Generator
17a-Hydroxy-progesterone	Generator
17Α-hydroxy-progesterone	Generator
delta(4)-Pregnene-17a-ol-3,20-dione	Generator
Δ(4)-pregnene-17α-ol-3,20-dione	Generator
Δ(4)-pregnene-17a-ol-3,20-dione	HMDB
17-alpha-Hydroxyprogesterone	HMDB
17-Hydroxypregn-4-ene-3,20-dione	HMDB
17-OH Progesterone	HMDB
17-OHP	HMDB
17a-Hydroxypregn-4-ene-3,20-dione	HMDB
17a-Hydroxyprogesterone	HMDB
17alpha-Hydroxyprogesterone	HMDB
D4-Pregnen-17a-ol-3,20-dione	HMDB
Gestageno	HMDB
Gestageno gador	HMDB
Pregn-4-en-17a-ol-3,20-dione	HMDB
Prodix	HMDB
Prodox	HMDB
17 Hydroxyprogesterone	HMDB
17-Hydroxyprogesterone, (17 alpha)-isomer	HMDB
17 alpha Hydroxyprogesterone	HMDB
17 alpha-Hydroxyprogesterone	HMDB
17-Hydroxyprogesterone, (9 beta, 10 alpha)-isomer	HMDB

Molecular Formula

C₂₁H₃₀O₃

Average Mass

330.4611

Monoisotopic Mass

330.219494826

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

68-96-2

SMILES

Not Available

InChI Identifier

InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

InChI Key

DBPWSSGDRRHUNT-CEGNMAFCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

17alpha-hydroxy steroid (CHEBI:17252 )
Progestagens (C01176 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030161 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Blood
Feces
Saliva
Testis
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192053	Aldo-keto reductase family 1 member C1	Unknown	Q04828	Homo sapiens
MMDBp0192107	Cytochrome P450 11B1, mitochondrial	Unknown	P15538	Homo sapiens
MMDBp0192653	Steroid 17-alpha-hydroxylase/17,20 lyase	Unknown	P05093	Homo sapiens
MMDBp0193970	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1	Unknown	P14060	Homo sapiens
MMDBp0193971	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2	Unknown	P26439	Homo sapiens
MMDBp0193997	Cytochrome P450 11B2, mitochondrial	Unknown	P19099	Homo sapiens
MMDBp0195936	Cytochrome P450, family 21, subfamily A, polypeptide 2	Enzyme	Q08AG9	Homo sapiens
MMDBp0196723	Steroid 21-hydroxylase	Unknown	P08686

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001478	17a-Hydroxypregnenolone	17-Hydroxyprogesterone	Not Available	VMH	12205101
MMDBr0001479	17a-Hydroxypregnenolone	17-Hydroxyprogesterone	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 2	VMH	12205101
MMDBr0001846	Progesterone	17-Hydroxyprogesterone	cytochrome P450, family 17, subfamily A, polypeptide 1	VMH	7893148
MMDBr0001850	17-Hydroxyprogesterone	Cortexolone	cytochrome P450, family 21, subfamily A, polypeptide 2	VMH	16541276 18381579 18381580
MMDBr0009624	Progesterone	17-Hydroxyprogesterone	cytochrome P450, family 17, subfamily A, polypeptide 1	VMH	30371894
MMDBr0009626	pregn-5-ene-3,20-dione-17-ol	17-Hydroxyprogesterone	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	30371894
MMDBr0009627	17-Hydroxyprogesterone	Cortexolone	cytochrome P450, family 21, subfamily A, polypeptide 2	VMH	30371894
MMDBr0009628	17-Hydroxyprogesterone	21-Deoxycortisol	cytochrome P450, family 11, subfamily B, polypeptide 1	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
11-beta-hydroxylase deficiency	Slight Increase	Association	Human Blood	HMDB	8933406
21-hydroxylase deficiency	Increased	Association	Human Blood	HMDB	11038205
21-hydroxylase deficiency		Association	Human Blood	HMDB	26336836
21-hydroxylase deficiency		Association	Human Blood	HMDB	10857554
21-hydroxylase deficiency	Increased	Association	Human Blood	HMDB	11826238
21-hydroxylase deficiency	Increased	Association	Human Blood	HMDB	25850025
Phenylketonuria	Slight Increase	Association	Human Blood	HMDB	17574536
Rheumatoid arthritis	Decreased	Association	Human Urine	HMDB	15249323
21-hydroxylase deficiency	Slight Decrease	Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
21-hydroxylase deficiency	Increased	Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Not Available	Neurodevelopment effects	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified			0.00130	0.0591	uM	Children (1-13 years old)	Both	11-beta-hydroxylase deficiency	HMDB	8933406
Human Blood	Detected and Quantified			0.216	0.265	uM	Newborn (0-30 days old)	Female	11-beta-hydroxylase deficiency	HMDB	8933406
Human Blood	Detected and Quantified	6.99				uM	Newborn (0-30 days old)	Female	21-hydroxylase deficiency	HMDB	11038205
Human Blood	Detected and Quantified	484.17				uM	Adolescent (13-18 years old)	Female	21-hydroxylase deficiency	HMDB	11038205
Human Blood	Detected and Quantified	<0.00300				uM	Newborn (0-30 days old)	Not Specified	21-hydroxylase deficiency	HMDB	26336836
Human Blood	Detected and Quantified	>0.300				uM	Newborn (0-30 days old)	Not Specified	21-hydroxylase deficiency	HMDB	26336836
Human Blood	Detected and Quantified	>0.303				uM	Children (1-13 years old)	Male	21-hydroxylase deficiency	HMDB	10857554
Human Blood	Detected and Quantified	>0.605				uM	Newborn (0-30 days old)	Male	21-hydroxylase deficiency	HMDB	10857554
Human Blood	Detected and Quantified			0.0388	0.252	uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	HMDB	11826238
Human Blood	Detected and Quantified	0.238		0.0251	0.611	uM	Adult (>18 years old)	Both	21-hydroxylase deficiency	HMDB	25850025
Human Blood	Detected and Quantified			3873.39	12951.64	uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	HMDB	11038205
Human Blood	Detected and Quantified	0.000908				uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	7951484
Human Blood	Detected and Quantified	0.0057				uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.009				uM	Adolescent (13-18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00170	0.00190			uM	Children (1-13 years old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00178	0.00144			uM	Infant (0-1 year old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00189	0.00100			uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00240	0.00220			uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00294	0.000900			uM	Newborn (0-30 days old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00330	0.00180			uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified			0.00450	0.184	uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified			0.00740	0.296	uM	Newborn (0-30 days old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified			0.0832	0.339	uM	Newborn (0-30 days old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	27476613
Human Blood	Detected and Quantified	<0.000605				uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	HMDB	18182448
Human Blood	Detected and Quantified			0.0147	0.0420	uM	Infant (0-1 year old)	Both	Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis	HMDB	16439592
Human Blood	Detected and Quantified	0.0032				uM	Newborn (0-30 days old)	Female	Bartter Syndrome, Type 2, Antenatal	HMDB	26069767
Human Blood	Detected and Quantified	1.522				uM	Infant (0-1 year old)	Both	Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency (CAH)	HMDB	19390483
Human Blood	Detected and Quantified	<0.000450				uM	Adult (>18 years old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535
Human Blood	Detected and Quantified	<0.000450				uM	Infant (0-1 year old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535
Human Blood	Detected and Quantified	<0.000450				uM	Adolescent (13-18 years old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535
Human Blood	Detected and Quantified	0.152		0.0022	0.302	uM	Adult (>18 years old)	Both	Phenylketonuria	HMDB	17574536
Human Urine	Detected and Quantified	0.00065	0.00011			umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	15249323
Human Urine	Detected and Quantified	0.00077	0.0002			umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	15249323
Human Urine	Detected and Quantified	<0.00015				umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	23159298
Human Blood	Detected and Quantified	<0.00250				uM	Children (1-13 years old)	Both	Normal	HMDB	26336836
Human Blood	Detected and Quantified	<0.00500				uM	Not Specified	Both	Normal	HMDB	8933406
Human Blood	Detected and Quantified	<0.00600				uM	Adult (>18 years old)	Male	Normal	HMDB	26336836
Human Blood	Detected and Quantified	<0.0121				uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	19390483
Human Blood	Detected and Quantified	<0.0450				uM	Newborn (0-30 days old)	Both	Normal	HMDB	8933406
Human Saliva	Detected and Quantified	<1.00				uM	Adult (>18 years old)	Both	Normal	HMDB	16155259
Human Blood	Detected and Quantified			0.000212	0.00233	uM	Newborn (0-30 days old)	Female	Normal	HMDB	18182448
Human Blood	Detected and Quantified			0.000300	0.00510	uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	16439592
Human Blood	Detected and Quantified			0.000500	0.0200	uM	Not Specified	Not Specified	Normal	HMDB	26069767
Human Urine	Detected and Quantified	0.0011		0	0.0019	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	23159298
Human Urine	Detected and Quantified	0.0013	0.00026			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15249323
Human Blood	Detected and Quantified	0.00151	0.000303			uM	Adult (>18 years old)	Female	Normal	HMDB	7951484
Human Blood	Detected and Quantified	0.00357		0.00109	0.00539	uM	Adult (>18 years old)	Both	Normal	HMDB	25850025
Human Blood	Detected and Quantified	0.00454	0.00363			uM	Adult (>18 years old)	Female	Normal	HMDB	11826238
Human Blood	Detected and Quantified	0.011		0.0003	0.023	uM	Infant (0-1 year old)	Both	Normal	HMDB	7776113
Human Blood	Detected and Quantified	0.0014		0.000030	0.0028	uM	Adult (>18 years old)	Both	21-hydroxylase deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	0.016		0.0090	0.024	uM	Children (1-13 years old)	Both	21-Hydroxylase Deficiency (CYP21)	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified			0.000300	0.00950	uM	Children (1 - 13 years old)	Both	Normal	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human Blood	Detected and Quantified			0.00061	0.00700	uM	Adult (>18 years old)	Male	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Blood	Detected and Quantified			0.00061	0.0136	uM	Adult (>18 years old)	Female	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal cortex	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000374

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021992

KNApSAcK ID

Not Available

Chemspider ID

6002

KEGG Compound ID

C01176

BioCyc ID

17-ALPHA-HYDROXYPROGESTERONE

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17252

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hampl R, Lachman M, Novak Z, Sulcova J, Starka L: Serum levels of steroid hormones in men with varicocele and oligospermia as compared to normozoospermic men. Exp Clin Endocrinol. 1992;100(3):117-9. doi: 10.1055/s-0029-1211189. [PubMed:1305061 ]
Lorence MC, Naville D, Graham-Lorence SE, Mack SO, Murry BA, Trant JM, Mason JI: 3 beta-hydroxysteroid dehydrogenase/delta 5----4-isomerase expression in rat and characterization of the testis isoform. Mol Cell Endocrinol. 1991 Sep;80(1-3):21-31. doi: 10.1016/0303-7207(91)90139-j. [PubMed:1955079 ]
Toscano V, Sancesario G, Bianchi P, Cicardi C, Casilli D, Giacomini P: Cerebrospinal fluid estrone in pseudotumor cerebri: a change in cerebral steroid hormone metabolism? J Endocrinol Invest. 1991 Feb;14(2):81-6. doi: 10.1007/BF03350271. [PubMed:2061573 ]
Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. doi: 10.1172/JCI114325. [PubMed:2808702 ]
Wilson SC, Hodgins MB, Scott JS: Incomplete masculinization due to a deficiency of 17 beta-hydroxysteroid dehydrogenase: comparison of prepubertal and peripubertal siblings. Clin Endocrinol (Oxf). 1987 Apr;26(4):459-69. doi: 10.1111/j.1365-2265.1987.tb00803.x. [PubMed:2820622 ]
al Saedi S, Dean H, Dent W, Cronin C: Reference ranges for serum cortisol and 17-hydroxyprogesterone levels in preterm infants. J Pediatr. 1995 Jun;126(6):985-7. doi: 10.1016/s0022-3476(95)70229-6. [PubMed:7776113 ]
Katagiri M, Kagawa N, Waterman MR: The role of cytochrome b5 in the biosynthesis of androgens by human P450c17. Arch Biochem Biophys. 1995 Mar 10;317(2):343-7. doi: 10.1006/abbi.1995.1173. [PubMed:7893148 ]
White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8. doi: 10.1002/humu.1380030408. [PubMed:8081391 ]
Sahin Y, Kelestimur F: 17-Hydroxyprogesterone responses to gonadotrophin-releasing hormone agonist buserelin and adrenocorticotrophin in polycystic ovary syndrome: investigation of adrenal and ovarian cytochrome P450c17alpha dysregulation. Hum Reprod. 1997 May;12(5):910-3. doi: 10.1093/humrep/12.5.910. [PubMed:9194638 ]
Kirchengast S, Hartmann B, Huber J: Serum levels of sex hormones, thyroid hormones, growth hormone, IGF I, and cortisol and their relations to body fat distribution in healthy women dependent on their menopausal status. Z Morphol Anthropol. 1996 Sep;81(2):223-34. [PubMed:9270338 ]
Ibanez L, de Zegher F, Potau N: Anovulation after precocious pubarche: early markers and time course in adolescence. J Clin Endocrinol Metab. 1999 Aug;84(8):2691-5. doi: 10.1210/jcem.84.8.5883. [PubMed:10443661 ]
Escobar-Morreale HF, San Millan JL, Smith RR, Sancho J, Witchel SF: The presence of the 21-hydroxylase deficiency carrier status in hirsute women: phenotype-genotype correlations. Fertil Steril. 1999 Oct;72(4):629-38. doi: 10.1016/s0015-0282(99)00317-9. [PubMed:10521100 ]
Bolt RJ, Van Weissenbruch MM, Popp-Snijders C, Sweep FG, Lafeber HN, Delemarre-van de Waal HA: Maturity of the adrenal cortex in very preterm infants is related to gestational age. Pediatr Res. 2002 Sep;52(3):405-10. doi: 10.1203/00006450-200209000-00017. [PubMed:12193676 ]
Gupta MK, Guryev OL, Auchus RJ: 5alpha-reduced C21 steroids are substrates for human cytochrome P450c17. Arch Biochem Biophys. 2003 Oct 15;418(2):151-60. doi: 10.1016/j.abb.2003.07.003. [PubMed:14522586 ]
Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. doi: 10.1016/s0039-128x(03)00115-6. [PubMed:14625002 ]
Gibney MJ, Walsh M, Brennan L, Roche HM, German B, van Ommen B: Metabolomics in human nutrition: opportunities and challenges. Am J Clin Nutr. 2005 Sep;82(3):497-503. doi: 10.1093/ajcn.82.3.497. [PubMed:16155259 ]

Showing metabocard for 17-Hydroxyprogesterone (MMDBc0047909)

MOL for #<Metabolite:0x00007fdb02f1c040>

3D MOL for #<Metabolite:0x00007fdb02f1c040>

3D SDF for #<Metabolite:0x00007fdb02f1c040>

3D-SDF for #<Metabolite:0x00007fdb02f1c040>

PDB for #<Metabolite:0x00007fdb02f1c040>

3D PDB for #<Metabolite:0x00007fdb02f1c040>

SMILES for #<Metabolite:0x00007fdb02f1c040>

INCHI for #<Metabolite:0x00007fdb02f1c040>

Structure for #<Metabolite:0x00007fdb02f1c040>

3D Structure for #<Metabolite:0x00007fdb02f1c040>