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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:01 UTC
HMDB IDHMDB0000374
Secondary Accession Numbers
  • HMDB00374
Metabolite Identification
Common Name17-Hydroxyprogesterone
Description17-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
Data?1582752127
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-dioneHMDB
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 HydroxyprogesteroneHMDB
17-Hydroxyprogesterone, (17 alpha)-isomerHMDB
17 alpha HydroxyprogesteroneHMDB
17 alpha-HydroxyprogesteroneHMDB
17-Hydroxyprogesterone, (9 beta, 10 alpha)-isomerHMDB
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[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
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
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.
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

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point219 - 220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0065 mg/mLNot Available
LogP3.17HANSCH,C ET AL. (1995)
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M-H]-Not Available185.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00000190
AllCCS[M+H]+Not Available185.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00000190
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP10(2.99) g/LALOGPS
logP10(3.4) g/LChemAxon
logS10(-4) g/LALOGPS
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
Polarizability37.9 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.86331661259
DarkChem[M-H]-176.25431661259
AllCCS[M+H]+182.8632859911
AllCCS[M-H]-188.83532859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
17-Hydroxyprogesterone,1TMS,#1CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3074.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
17-Hydroxyprogesterone,1TMS,#2CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2919.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
17-Hydroxyprogesterone,1TMS,#3C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C2959.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
17-Hydroxyprogesterone,1TBDMS,#1CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3308.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
17-Hydroxyprogesterone,1TBDMS,#2CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3187.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
17-Hydroxyprogesterone,1TBDMS,#3C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3219.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (2 MEOX; 1 TMS)splash10-004l-4911000000-d40ba45835d1ee1b6c412014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 17-Hydroxyprogesterone EI-B (Non-derivatized)splash10-002o-9651000000-b44110f9abcffa42ce352017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (Non-derivatized)splash10-004l-4911000000-d40ba45835d1ee1b6c412017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9f-4595000000-89ccbf45dbf9f474bd2f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (1 TMS) - 70eV, Positivesplash10-007c-3249000000-3570f5d248c0ee0716ee2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-002f-9731000000-48d2266d41955ffa9ce42014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0009000000-a157e4b4aa18bdbc25312012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-052b-5900000000-42494c0ef4b45cfa5cf42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-052b-9700000000-d8a942a3dfdb061bd5c32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone EI-B (HITACHI M-80) , Positive-QTOFsplash10-002o-9651000000-b0c55e50343bf8ab30772012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone , positive-QTOFsplash10-0a4j-4930000000-c5056c0aac78a148ea922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone 45V, Positive-QTOFsplash10-052b-5910000000-fcf792a46552ed6e00282021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone 60V, Positive-QTOFsplash10-052b-6900000000-6970a665800f041e96122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone 30V, Positive-QTOFsplash10-0532-6966000000-f57233040f10efef4ba92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone 15V, Positive-QTOFsplash10-001i-0009000000-0cff8a9a4549636b3f422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone 75V, Positive-QTOFsplash10-0a4j-9800000000-3aaefadc8d2e4ad3a5222021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 17-Hydroxyprogesterone 90V, Positive-QTOFsplash10-0a6s-9600000000-17d56b65d46a46d9f6532021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 10V, Positive-QTOFsplash10-001i-0029000000-0af1b9a61aa5a9d514a42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 20V, Positive-QTOFsplash10-0lzi-0295000000-0510776f8fa0d9ddcb6a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 40V, Positive-QTOFsplash10-00li-3970000000-1655d52be304b45389ae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 10V, Negative-QTOFsplash10-004i-0009000000-bc250df2e599669d113e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 20V, Negative-QTOFsplash10-002r-0097000000-41db31593b4f58cd4bc42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 40V, Negative-QTOFsplash10-0bti-0092000000-464375e5c4a93d5d20b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 10V, Positive-QTOFsplash10-01q9-0019000000-bf0f51dc62b5855371a32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 20V, Positive-QTOFsplash10-03di-0922000000-6997f50bd7502e7518f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 40V, Positive-QTOFsplash10-0cdi-3910000000-051d81ed4aaf877bebaf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 10V, Negative-QTOFsplash10-004i-0039000000-8b733a2d2a661578ddbe2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 20V, Negative-QTOFsplash10-004r-0049000000-1387b7ed039fc5504c872021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Hydroxyprogesterone 40V, Negative-QTOFsplash10-00kr-0091000000-dc494a2f8f424f99a5742021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
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
  • Testis
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 but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified<0.00015 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified0.0011 (0-0.0019) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
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 Quantified484.17 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 Quantified3873.39-12951.64 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
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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
FooDB IDFDB021992
KNApSAcK IDNot Available
Chemspider ID6002
KEGG Compound IDC01176
BioCyc ID17-ALPHA-HYDROXYPROGESTERONE
BiGG ID36989
Wikipedia LinkHydroxyprogesterone
METLIN ID5363
PubChem Compound6238
PDB IDNot Available
ChEBI ID17252
Food Biomarker OntologyNot Available
VMH ID17AHPRGSTRN
MarkerDB IDMDB00000154
Good Scents IDrw1368781
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 ]
  16. 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 ]

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