Showing metabocard for 17a-Hydroxypregnenolone (BMDB0000363)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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 IDFDB021982
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

Enzyme Details
1. Steroid 17-alpha-hydroxylase/17,20 lyase
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