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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:01 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
Not AvailableNot Available
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 Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available185.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00000190
[M+H]+Not Available185.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00000190
Predicted Molecular 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
Polarizability37.9 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic 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
DeepCCS[M-2H]-213.69130932474
DeepCCS[M+Na]+188.78230932474
AllCCS[M+H]+182.932859911
AllCCS[M+H-H2O]+180.132859911
AllCCS[M+NH4]+185.532859911
AllCCS[M+Na]+186.232859911
AllCCS[M-H]-188.832859911
AllCCS[M+Na-2H]-189.232859911
AllCCS[M+HCOO]-189.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
17-Hydroxyprogesterone[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C3946.4Standard polar33892256
17-Hydroxyprogesterone[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C2769.3Standard non polar33892256
17-Hydroxyprogesterone[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C2983.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
17-Hydroxyprogesterone,1TMS,isomer #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 polar33892256
17-Hydroxyprogesterone,1TMS,isomer #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 polar33892256
17-Hydroxyprogesterone,1TMS,isomer #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 polar33892256
17-Hydroxyprogesterone,2TMS,isomer #1CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3001.1Semi standard non polar33892256
17-Hydroxyprogesterone,2TMS,isomer #1CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2892.6Standard non polar33892256
17-Hydroxyprogesterone,2TMS,isomer #1CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3226.4Standard polar33892256
17-Hydroxyprogesterone,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3048.6Semi standard non polar33892256
17-Hydroxyprogesterone,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C2835.0Standard non polar33892256
17-Hydroxyprogesterone,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3293.2Standard polar33892256
17-Hydroxyprogesterone,2TMS,isomer #3C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2909.1Semi standard non polar33892256
17-Hydroxyprogesterone,2TMS,isomer #3C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2861.4Standard non polar33892256
17-Hydroxyprogesterone,2TMS,isomer #3C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3342.1Standard polar33892256
17-Hydroxyprogesterone,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2983.4Semi standard non polar33892256
17-Hydroxyprogesterone,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2934.6Standard non polar33892256
17-Hydroxyprogesterone,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3275.3Standard polar33892256
17-Hydroxyprogesterone,1TBDMS,isomer #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 polar33892256
17-Hydroxyprogesterone,1TBDMS,isomer #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 polar33892256
17-Hydroxyprogesterone,1TBDMS,isomer #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 polar33892256
17-Hydroxyprogesterone,2TBDMS,isomer #1CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3492.2Semi standard non polar33892256
17-Hydroxyprogesterone,2TBDMS,isomer #1CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3364.5Standard non polar33892256
17-Hydroxyprogesterone,2TBDMS,isomer #1CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3440.2Standard polar33892256
17-Hydroxyprogesterone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[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@@]21C3551.5Semi standard non polar33892256
17-Hydroxyprogesterone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[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@@]21C3343.2Standard non polar33892256
17-Hydroxyprogesterone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[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@@]21C3498.0Standard polar33892256
17-Hydroxyprogesterone,2TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[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@@]21C3417.3Semi standard non polar33892256
17-Hydroxyprogesterone,2TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[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@@]21C3306.9Standard non polar33892256
17-Hydroxyprogesterone,2TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[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@@]21C3558.6Standard polar33892256
17-Hydroxyprogesterone,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3729.1Semi standard non polar33892256
17-Hydroxyprogesterone,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3566.3Standard non polar33892256
17-Hydroxyprogesterone,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3515.6Standard polar33892256
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
Predicted GC-MSPredicted GC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Hydroxyprogesterone GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart 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 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
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