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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 08:52:00 UTC
HMDB IDHMDB0000374
Secondary Accession Numbers
  • HMDB00374
Metabolite Identification
Common Name17-Hydroxyprogesterone
DescriptionIt serves as an intermediate in the biosynthesis of hydrocortisone and gonadal steroid hormones. It is derived from progesterone via 17-hydroxylase, a P450c17 enzyme, or from 17-hydroxypregnenolone via 3β-hydroxysteroid dehydrogenase/Δ5-4 isomerase. 17-Hydroxyprogesterone is a natural progestin and in pregnancy increases in the third trimester primarily due to fetal adrenal production. This hormone 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 and 11β-hydroxylase, lead to a build-up of 17OHP. In contrast, the rare patient with 17α-hydroxylase deficiency will have very low or undetectable levels of 17OHP. 17OHP levels can also be used to measure contribution of progestational activity of the corpus luteum during pregnancy as progesterone but not 17OHP is also contributed by the placenta.
Structure
Thumb
Synonyms
ValueSource
17-Hydroxypregn-4-en-3,20-dioneChEBI
17alpha-Hydroxy-4-pregnene-3,20-dioneChEBI
17alpha-Hydroxy-progesteroneChEBI
delta(4)-Pregnene-17alpha-ol-3,20-dioneChEBI
HidroxiprogesteronaChEBI
HydroxyprogesteroneChEBI
HydroxyprogesteronumChEBI
Pregn-4-ene-3,20-dione-17-olChEBI
17a-Hydroxy-4-pregnene-3,20-dioneGenerator
17α-hydroxy-4-pregnene-3,20-dioneGenerator
17a-Hydroxy-progesteroneGenerator
17α-hydroxy-progesteroneGenerator
delta(4)-Pregnene-17a-ol-3,20-dioneGenerator
δ(4)-pregnene-17α-ol-3,20-dioneGenerator
δ(4)-pregnene-17a-ol-3,20-dioneGenerator
17-alpha-HydroxyprogesteroneHMDB
17-Hydroxypregn-4-ene-3,20-dioneHMDB
17-OH ProgesteroneHMDB
17-OHPHMDB
17a-Hydroxypregn-4-ene-3,20-dioneHMDB
17a-HydroxyprogesteroneHMDB
17alpha-HydroxyprogesteroneHMDB
D4-Pregnen-17a-ol-3,20-dioneHMDB
GestagenoHMDB
gestageno GadorHMDB
Pregn-4-en-17a-ol-3,20-dioneHMDB
ProdixHMDB
ProdoxHMDB
17 HydroxyprogesteroneMeSH
17-Hydroxyprogesterone, (17 alpha)-isomerMeSH
17 alpha HydroxyprogesteroneMeSH
17 alpha-HydroxyprogesteroneMeSH
17-Hydroxyprogesterone, (9 beta, 10 alpha)-isomerMeSH
Chemical FormulaC21H30O3
Average Molecular Weight330.4611
Monoisotopic Molecular Weight330.219494826
IUPAC Name(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Namehydroxyprogesterone
CAS Registry Number68-96-2
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
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 KeyDBPWSSGDRRHUNT-CEGNMAFCSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point219 - 220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0065 mg/mLNot Available
LogP3.17HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP2.99ALOGPS
logP3.4ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)12.7ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.11 m³·mol⁻¹ChemAxon
Polarizability37.93 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-004l-4911000000-d40ba45835d1ee1b6c41View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002o-9651000000-b44110f9abcffa42ce35View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-4911000000-d40ba45835d1ee1b6c41View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9f-4595000000-89ccbf45dbf9f474bd2fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007c-3249000000-3570f5d248c0ee0716eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0009000000-a157e4b4aa18bdbc2531View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-5900000000-42494c0ef4b45cfa5cf4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9700000000-d8a942a3dfdb061bd5c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-002o-9651000000-b0c55e50343bf8ab3077View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4j-4930000000-c5056c0aac78a148ea92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-0af1b9a61aa5a9d514a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lzi-0295000000-0510776f8fa0d9ddcb6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-3970000000-1655d52be304b45389aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-bc250df2e599669d113eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-0097000000-41db31593b4f58cd4bc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bti-0092000000-464375e5c4a93d5d20b3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-002f-9731000000-48d2266d41955ffa9ce4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000212-0.00233 uMNewborn (0-30 days old)Female
Normal
details
BloodDetected and Quantified<0.0121 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified0.00357 (0.00109-0.00539) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00454 +/- 0.00363 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.011 (0.0003-0.023) uMInfant (0-1 year old)BothNormal details
BloodDetected and Quantified0.00151 +/- 0.000303 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.000500-0.0200 uMNot SpecifiedNot SpecifiedNormal details
BloodDetected and Quantified<0.0450 uMNewborn (0-30 days old)BothNormal details
BloodDetected and Quantified0.000300-0.00510 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified<0.00500 uMNot SpecifiedBothNormal details
BloodDetected and Quantified0.000300-0.00950 uMChildren (1 - 13 years old)BothNormal
    • Physician's Guide...
details
BloodDetected and Quantified0.00061 - 0.0136 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00061 - 0.00700 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified<0.00250 uMChildren (1-13 years old)BothNormal details
BloodDetected and Quantified<0.00600 uMAdult (>18 years old)MaleNormal details
SalivaDetected and Quantified<1.00 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0013 +/- 0.00026 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.000605 uMNewborn (0-30 days old)Female
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
details
BloodDetected and Quantified0.0832-0.339 uMNewborn (0-30 days old)MaleAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified>0.303 uMChildren (1-13 years old)Male21-hydroxylase deficiency details
BloodDetected and Quantified>0.605 uMNewborn (0-30 days old)Male21-hydroxylase deficiency details
BloodDetected and Quantified12951.6 uMAdolescent (13-18 years old)Female
21-hydroxylase deficiency
details
BloodDetected and Quantified6.99 uMNewborn (0-30 days old)Female
21-hydroxylase deficiency
details
BloodDetected and Quantified484.172-3873.376 uMAdult (>18 years old)Female
21-hydroxylase deficiency
details
BloodDetected and Quantified1.522 uMInfant (0-1 year old)Both
Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency (CAH)
details
BloodDetected and Quantified0.238 (0.0251-0.611) uMAdult (>18 years old)Both21-hydroxylase deficiency details
BloodDetected and Quantified0.0388-0.252 uMAdult (>18 years old)Female21-hydroxylase deficiency details
BloodDetected and Quantified0.00294 +/- 0.000900 uMNewborn (0-30 days old)Not Specified
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00170 +/- 0.00190 uMChildren (1-13 years old)Not Specified
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.0057 uMAdult (>18 years old)Male
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.009 uMAdolescent (13-18 years old)Male
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00740-0.296 uMNewborn (0-30 days old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00450-0.184 uMChildren (1-13 years old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00178 +/- 0.00144 uMInfant (0-1 year old)Not SpecifiedAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.00189 +/- 0.00100 uMChildren (1-13 years old)BothAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.00240 +/- 0.00220 uMAdult (>18 years old)FemaleAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.00330 +/- 0.00180 uMAdult (>18 years old)MaleAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.000908 uMAdult (>18 years old)Female
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified<0.000450 uMAdult (>18 years old)FemaleLipoid Adrenal Hyperplasia details
BloodDetected and Quantified<0.000450 uMInfant (0-1 year old)FemaleLipoid Adrenal Hyperplasia details
BloodDetected and Quantified<0.000450 uMAdolescent (13-18 years old)FemaleLipoid Adrenal Hyperplasia details
BloodDetected and Quantified0.0032 uMNewborn (0-30 days old)FemaleBartter Syndrome, Type 2, Antenatal details
BloodDetected and Quantified0.00130-0.0591 uMChildren (1-13 years old)Both
11-beta-hydroxylase deficiency
details
BloodDetected and Quantified0.216-0.265 uMNewborn (0-30 days old)Female
11-beta-hydroxylase deficiency
details
BloodDetected and Quantified0.0147-0.0420 uMInfant (0-1 year old)Both
Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis
details
BloodDetected and Quantified0.152 (0.0022- 0.302) uMAdult (>18 years old)BothPhenylketonuria details
BloodDetected and Quantified0.0014 (0.000030-0.0028) uMAdult (>18 years old)Both21-hydroxylase deficiency
    • MetaGene: Metabol...
details
BloodDetected and Quantified0.016 (0.0090-0.024) uMChildren (1-13 years old)Both21-Hydroxylase Deficiency (CYP21)
    • MetaGene: Metabol...
details
BloodDetected and Quantified<0.00300 uMNewborn (0-30 days old)Not Specified21-hydroxylase deficiency details
BloodDetected and Quantified>0.300 uMNewborn (0-30 days old)Not Specified21-hydroxylase deficiency details
UrineDetected and Quantified0.0017 +/- 0.00034 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
UrineDetected and Quantified0.00065 +/- 0.00011 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.00077 +/- 0.0002 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.0022 +/- 0.00058 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
Associated Disorders and Diseases
Disease References
11-beta-Hydroxylase deficiency
  1. Burren CP, Montalto J, Yong AB, Batch JA: CYP11 beta 1 (11-beta-hydroxylase) deficiency in congenital adrenal hyperplasia. J Paediatr Child Health. 1996 Oct;32(5):433-8. [PubMed:8933406 ]
21-Hydroxylase deficiency
  1. Turcu AF, Rege J, Chomic R, Liu J, Nishimoto HK, Else T, Moraitis AG, Palapattu GS, Rainey WE, Auchus RJ: Profiles of 21-Carbon Steroids in 21-hydroxylase Deficiency. J Clin Endocrinol Metab. 2015 Jun;100(6):2283-90. doi: 10.1210/jc.2015-1023. Epub 2015 Apr 7. [PubMed:25850025 ]
  2. White PC, Speiser PW: Congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Endocr Rev. 2000 Jun;21(3):245-91. doi: 10.1210/edrv.21.3.0398. [PubMed:10857554 ]
  3. Warinner SA, Zimmerman D, Thompson GB, Grant CS: Study of three patients with congenital adrenal hyperplasia treated by bilateral adrenalectomy. World J Surg. 2000 Nov;24(11):1347-52. [PubMed:11038205 ]
  4. Gmyrek GA, New MI, Sosa RE, Poppas DP: Bilateral laparoscopic adrenalectomy as a treatment for classic congenital adrenal hyperplasia attributable to 21-hydroxylase deficiency. Pediatrics. 2002 Feb;109(2):E28. [PubMed:11826238 ]
  5. Falhammar H, Wedell A, Nordenstrom A: Biochemical and genetic diagnosis of 21-hydroxylase deficiency. Endocrine. 2015 Nov;50(2):306-14. doi: 10.1007/s12020-015-0731-6. Epub 2015 Sep 4. [PubMed:26336836 ]
  6. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
  1. Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ]
  2. Lutfallah C, Wang W, Mason JI, Chang YT, Haider A, Rich B, Castro-Magana M, Copeland KC, David R, Pang S: Newly proposed hormonal criteria via genotypic proof for type II 3beta-hydroxysteroid dehydrogenase deficiency. J Clin Endocrinol Metab. 2002 Jun;87(6):2611-22. doi: 10.1210/jcem.87.6.8615. [PubMed:12050224 ]
  3. Guven A, Polat S: Testicular Adrenal Rest Tumor in Two Brothers with a Novel Mutation in the 3-Beta-Hydroxysteroid Dehydrogenase-2 Gene. J Clin Res Pediatr Endocrinol. 2017 Mar 1;9(1):85-90. doi: 10.4274/jcrpe.3306. Epub 2016 Jul 29. [PubMed:27476613 ]
Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency
  1. Schwarz E, Liu A, Randall H, Haslip C, Keune F, Murray M, Longo N, Pasquali M: Use of steroid profiling by UPLC-MS/MS as a second tier test in newborn screening for congenital adrenal hyperplasia: the Utah experience. Pediatr Res. 2009 Aug;66(2):230-5. doi: 10.1203/PDR.0b013e3181aa3777. [PubMed:19390483 ]
Phenylketonuria
  1. Elvers LH, Loeber JG, Dhondt JL, Fukushi M, Hannon WH, Torresani T, Webster D: First ISNS Reference Preparation for Neonatal Screening for thyrotropin, phenylalanine and 17alpha-hydroxyprogesterone in blood spots. J Inherit Metab Dis. 2007 Aug;30(4):609. Epub 2007 Jun 14. [PubMed:17574536 ]
Rheumatoid arthritis
  1. Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8. [PubMed:15249323 ]
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
  1. Kim CJ, Lin L, Huang N, Quigley CA, AvRuskin TW, Achermann JC, Miller WL: Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc. J Clin Endocrinol Metab. 2008 Mar;93(3):696-702. doi: 10.1210/jc.2007-2330. Epub 2008 Jan 8. [PubMed:18182448 ]
Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis
  1. Fukami M, Hasegawa T, Horikawa R, Ohashi T, Nishimura G, Homma K, Ogata T: Cytochrome P450 oxidoreductase deficiency in three patients initially regarded as having 21-hydroxylase deficiency and/or aromatase deficiency: diagnostic value of urine steroid hormone analysis. Pediatr Res. 2006 Feb;59(2):276-80. doi: 10.1203/01.pdr.0000195825.31504.28. [PubMed:16439592 ]
Bartter Syndrome, Type 2, Antenatal
  1. Chan WK, To KF, Tong JH, Law CW: Paradoxical hypertension and salt wasting in Type II Bartter syndrome. Clin Kidney J. 2012 Jun;5(3):217-20. doi: 10.1093/ckj/sfs026. Epub 2012 Mar 29. [PubMed:26069767 ]
Lipoid Congenital Adrenal Hyperplasia
  1. Fujieda K, Tajima T, Nakae J, Sageshima S, Tachibana K, Suwa S, Sugawara T, Strauss JF 3rd: Spontaneous puberty in 46,XX subjects with congenital lipoid adrenal hyperplasia. Ovarian steroidogenesis is spared to some extent despite inactivating mutations in the steroidogenic acute regulatory protein (StAR) gene. J Clin Invest. 1997 Mar 15;99(6):1265-71. doi: 10.1172/JCI119284. [PubMed:9077535 ]
Associated OMIM IDs
  • 261600 (Phenylketonuria)
  • 201910 (21-Hydroxylase deficiency)
  • 201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
  • 202010 (11-beta-Hydroxylase deficiency)
  • 201750 (Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis)
  • 613743 (Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete)
  • 201910 (Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency)
  • 241200 (Bartter Syndrome, Type 2, Antenatal)
  • 201710 (Lipoid Congenital Adrenal Hyperplasia)
  • 180300 (Rheumatoid arthritis)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021992
KNApSAcK IDNot Available
Chemspider ID6002
KEGG Compound IDC01176
BioCyc ID17-ALPHA-HYDROXYPROGESTERONE
BiGG ID36989
Wikipedia LinkHydroxyprogesterone
METLIN ID5363
PubChem Compound6238
PDB ID3QZ
ChEBI ID17252
References
Synthesis ReferenceSchneider, Carlos; Silva, Mario; Zunza, Hilda; Becerra, Jose. Synthesis of 17.alpha.-hydroxyprogesterone from androstenedione. Boletin de la Sociedad Chilena de Quimica (1999), 44(2), 167-172.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8. [PubMed:8081391 ]
  2. Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. [PubMed:2808702 ]
  3. Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [PubMed:14625002 ]
  4. 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. [PubMed:16155259 ]
  5. 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. [PubMed:9194638 ]
  6. 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 ]
  7. 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. [PubMed:1305061 ]
  8. 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. [PubMed:10443661 ]
  9. 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. [PubMed:7893148 ]
  10. 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. [PubMed:7776113 ]
  11. 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. [PubMed:14522586 ]
  12. 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. [PubMed:10521100 ]
  13. 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. [PubMed:2820622 ]
  14. 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. [PubMed:2061573 ]
  15. 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. [PubMed:12193676 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
Reactions
17alpha,20alpha-Dihydroxypregn-4-en-3-one + NAD(P)(+) → 17-Hydroxyprogesterone + NAD(P)Hdetails
General function:
Involved in monooxygenase activity
Specific function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular weight:
57572.44
Reactions
17-Hydroxyprogesterone + Reduced ferredoxin + Oxygen → 21-Deoxycortisol + Oxidized ferredoxin + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:
CYP17A1
Uniprot ID:
P05093
Molecular weight:
57369.995
Reactions
Progesterone + Reduced acceptor + Oxygen → 17-Hydroxyprogesterone + Acceptor + Waterdetails
17-Hydroxyprogesterone + Reduced acceptor + Oxygen → Androstenedione + Acetic acid + Acceptor + Waterdetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:
HSD3B1
Uniprot ID:
P14060
Molecular weight:
42251.25
Reactions
17a-Hydroxypregnenolone + NAD → 17-Hydroxyprogesterone + NADH + Hydrogen Iondetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
HSD3B2
Uniprot ID:
P26439
Molecular weight:
42051.845
Reactions
17a-Hydroxypregnenolone + NAD → 17-Hydroxyprogesterone + NADH + Hydrogen Iondetails
General function:
Involved in monooxygenase activity
Specific function:
Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:
CYP11B2
Uniprot ID:
P19099
Molecular weight:
57559.62
Reactions
17-Hydroxyprogesterone + Reduced ferredoxin + Oxygen → 21-Deoxycortisol + Oxidized ferredoxin + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP21A2
Uniprot ID:
Q08AG9
Molecular weight:
55972.9
General function:
Not Available
Specific function:
Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:
CYP21A2
Uniprot ID:
P08686
Molecular weight:
56000.94
Reactions
17-Hydroxyprogesterone + Reduced acceptor + Oxygen → Cortexolone + Acceptor + Waterdetails