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Record Information
Version1.0
Creation Date2016-09-30 22:29:20 UTC
Update Date2020-06-04 20:39:42 UTC
BMDB IDBMDB0000363
Secondary Accession Numbers
  • BMDB00363
Metabolite Identification
Common Name17a-Hydroxypregnenolone
Description17a-17a-17a-hydroxypregnenolone 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. Thus, 17a-17a-hydroxypregnenolone is considered to be a steroid lipid molecule. 17a-17a-17a-hydroxypregnenolone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 17a-17a-17a-hydroxypregnenolone participates in a number of enzymatic reactions, within cattle. In particular, 17a-17a-17a-hydroxypregnenolone can be converted into 17-hydroxyprogesterone; which is mediated by the enzyme 3-beta-HSD 1. In addition, 17a-17a-17a-hydroxypregnenolone can be biosynthesized from pregnenolone through the action of the enzyme steroid 17-alpha-hydroxylase/17,20 lyase. In cattle, 17a-17a-hydroxypregnenolone is involved in the metabolic pathway called the steroidogenesis pathway. 17a-17a-17a-hydroxypregnenolone is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(3beta)-3,17-Dihydroxypregn-5-en-20-oneChEBI
17-HydroxypregnenoloneChEBI
5-Pregnen-3beta,17alpha-diol-20-oneChEBI
(3b)-3,17-Dihydroxypregn-5-en-20-oneGenerator
(3Β)-3,17-dihydroxypregn-5-en-20-oneGenerator
5-Pregnen-3b,17a-diol-20-oneGenerator
5-Pregnen-3β,17α-diol-20-oneGenerator
17-Hydroxy-D5-pregnenoloneHMDB
17-OH-PregnenoloneHMDB
17a-HydroxypregnoloneHMDB
17alpha-HydroxypregnanoloneHMDB
17alpha-HydroxypregnenoloneHMDB
3b,17-Dihydroxy-5-pregnen-20-oneHMDB
3b,17-Dihydroxy-pregn-5-en-20-oneHMDB
3b,17a-Dihydroxypregn-5-en-20-oneHMDB
17alpha HydroxypregnenoloneHMDB
HydroxypregnenoloneHMDB
17 HydroxypregnenoloneHMDB
17 alpha HydroxypregnenoloneHMDB
17-Hydroxypregnenolone, (3alpha)-isomerHMDB
17-Hydroxypregnenolone, (3beta,13alpha)-isomerHMDB
17-alpha-HydroxypregnenoloneHMDB
17 alpha-HydroxypregnenoloneHMDB
17-Hydroxypregnenolone, (3beta,13alpha,17alpha)-isomerHMDB
17-Hydroxypregnenolone, (3beta,17alpha)-isomerHMDB
Chemical FormulaC21H32O3
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
IUPAC Name1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
Traditional Name1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone
CAS Registry Number387-79-1
SMILES
[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O3/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/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1
InChI KeyJERGUCIJOXJXHF-TVWVXWENSA-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-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point266 - 271 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.15ALOGPS
logP2.83ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)12.7ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.16 m³·mol⁻¹ChemAxon
Polarizability38.66 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-054x-4900000000-df86d10979d808f20e67View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0a73-3910000000-7a0eea991ac4d2fac97eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f89-2891000000-3605ad7dd57f97382115View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ff0-3792000000-974e157d4c25e376b004View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-054x-4900000000-df86d10979d808f20e67View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a73-3910000000-7a0eea991ac4d2fac97eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-3295000000-48ed11374901b134a70dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-0111900000-e55e71b4d8c63cde89c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0039000000-28c103ca6cdf072557bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0900000000-ae3004bb674d9632cd0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-0900000000-a2f467560b451d5c9b0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0f89-2891000000-82e62584fff36943bcbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0029000000-131b75950fb7123106d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015i-0094000000-2a48017855d3965d5626View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g29-2690000000-3d1b2b0525a2f6da149cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-4c286aa6d88850e66ba9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-008i-0098000000-77ce542de402b225ac27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avr-0092000000-e39f57cc01b46a017728View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen Locations
  • Adrenal Cortex
  • Blood
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adrenal CortexExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected and Quantified0.00022 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified0.00204 uMNot SpecifiedNot Specified
Normal
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00171 uMNot SpecifiedNot Specified
Treated with estradiol benzoate and progesterone
details
BloodDetected and Quantified0.00383 uMNot SpecifiedNot Specified
Treated with estradiol benzoate
details
HMDB IDHMDB0000363
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030278
KNApSAcK IDNot Available
Chemspider ID82579
KEGG Compound IDC05138
BioCyc IDCPD66-23
BiGG ID45199
Wikipedia Link17-Hydroxypregnenolone
METLIN ID5352
PubChem Compound91451
PDB IDNot Available
ChEBI ID28750
References
Synthesis ReferenceKaspar, Emanuel; Hiersemann, Wolfgang; Schenck, Martin. Preparation from their esters of steroid alcohols that are sensitive to acids and alkali. (1958), DE 1028572 19580424 CAN 54:74845 AN 1960:74845 CAPLUS
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in corticoid and androgen biosynthesis. Catalyzes 17-alpha hydroxylation of C21 steroids, which is common for both pathways. A second oxidative step, required only for androgen synthesis, involves an acyl-carbon cleavage. The 17-alpha hydroxy intermediates, as part of adrenal glucocorticoids biosynthesis pathway, are precursors of cortisol. Hydroxylates steroid hormones, pregnenolone and progesterone to form 17-alpha hydroxy metabolites, followed by the cleavage of the C17-C20 bond to form C19 steroids, dehydroepiandrosterone (DHEA) and androstenedione. Has 16-alpha hydroxylase activity. Catalyzes 16-alpha hydroxylation of 17-alpha hydroxy pregnenolone, followed by the cleavage of the C17-C20 bond to form 16-alpha-hydroxy DHEA. Also 16-alpha hydroxylates androgens, relevant for estriol synthesis. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:
CYP17A1
Uniprot ID:
P05185
Molecular weight:
57244.0
Reactions
17a-Hydroxypregnenolone → Dehydroepiandrosteronedetails