You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Livestock Metabolome Database.
Record Information
Version1.0
Creation Date2016-07-13 19:43:23 UTC
Update Date2016-07-19 23:06:32 UTC
LmdbLMDB00147
Secondary Accession NumbersNone
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-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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-004l-4911000000-d40ba45835d1ee1b6c41Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002o-9651000000-b44110f9abcffa42ce35Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-4911000000-d40ba45835d1ee1b6c41Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9f-4595000000-89ccbf45dbf9f474bd2fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007c-3249000000-3570f5d248c0ee0716eeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0009000000-a157e4b4aa18bdbc2531Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-5900000000-42494c0ef4b45cfa5cf4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9700000000-d8a942a3dfdb061bd5c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-002o-9651000000-b0c55e50343bf8ab3077Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4j-4930000000-c5056c0aac78a148ea92Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-052b-5910000000-fcf792a46552ed6e0028Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-052b-6900000000-6970a665800f041e9612Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0532-6966000000-f57233040f10efef4ba9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-0009000000-0cff8a9a4549636b3f42Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0a4j-9800000000-3aaefadc8d2e4ad3a522Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0a6s-9600000000-17d56b65d46a46d9f653Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-0af1b9a61aa5a9d514a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lzi-0295000000-0510776f8fa0d9ddcb6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-3970000000-1655d52be304b45389aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-bc250df2e599669d113eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-0097000000-41db31593b4f58cd4bc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bti-0092000000-464375e5c4a93d5d20b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0019000000-bf0f51dc62b5855371a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0922000000-6997f50bd7502e7518f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdi-3910000000-051d81ed4aaf877bebafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0039000000-8b733a2d2a661578ddbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-0049000000-1387b7ed039fc5504c87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-0091000000-dc494a2f8f424f99a574Spectrum
MSMass Spectrum (Electron Ionization)splash10-002f-9731000000-48d2266d41955ffa9ce4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected and Quantified0.000395 uMNot AvailableBovine details
SerumDetected and Quantified0.000999 uMNot AvailableBovine details
SerumDetected and Quantified<0.000675 uMNot AvailableBovine details
SerumDetected and Quantified<0.000675 uMNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0000374
FooDB IDFDB021992
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID36989
BioCyc ID17-ALPHA-HYDROXYPROGESTERONE
METLIN ID5363
PDB IDNot Available
Wikipedia LinkHydroxyprogesterone
Chemspider ID6002
ChEBI ID17252
PubChem Compound ID6238
Kegg Compound IDC01176
YMDB IDNot Available
ECMDB IDM2MDB005821
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available