Record Information
Version1.0
Creation date2011-09-21 00:06:39 UTC
Update date2015-10-09 22:28:53 UTC
Primary IDFDB021992
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number68-96-2
Structure
Thumb
Synonyms
SynonymSource
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
17-alpha-hydroxyprogesteronehmdb
17-Hydroxyprogesteronehmdb
17alpha-hydroxyprogesteronehmdb
17α-hydroxy-4-pregnene-3,20-dioneGenerator
17α-hydroxy-progesteroneGenerator
17α-hydroxyprogesteroneGenerator
Gestageno Gadorhmdb
δ(4)-pregnene-17a-ol-3,20-dioneGenerator
δ(4)-pregnene-17α-ol-3,20-dioneGenerator
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
Polarizability37.9 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H30O3
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight330.4611
Monoisotopic Molecular Weight330.219494826
Classification
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
ChemSpider ID6002
ChEMBL IDCHEMBL1062
KEGG Compound IDC01176
Pubchem Compound ID6238
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00374
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36989
KNApSAcK IDNot Available
HET ID3QZ
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID17-Hydroxyprogesterone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 21, subfamily A, polypeptide 2CYP21A2Q08AG9
Pathways
NameSMPDB LinkKEGG Link
Androgen and Estrogen MetabolismSMP00068 map00150
SteroidogenesisSMP00130 map00140
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference