Showing metabocard for 17a,21-Dihydroxypreg-nenolone (BMDB0006762)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:42 UTC
Update Date2020-05-21 16:28:52 UTC
BMDB IDBMDB0006762
Secondary Accession Numbers
  • BMDB06762
Metabolite Identification
Common Name17a,21-Dihydroxypreg-nenolone
Description17alpha,21-Dihydroxypregnenolone, also known as 17alpha,21-dihydroxypregnenolone, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, 17alpha,21-dihydroxypregnenolone is considered to be a steroid lipid molecule. 17alpha,21-Dihydroxypregnenolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 17alpha,21-Dihydroxypregnenolone exists in all living organisms, ranging from bacteria to humans. 17alpha,21-Dihydroxypregnenolone participates in a number of enzymatic reactions, within cattle. In particular, 17alpha,21-Dihydroxypregnenolone can be biosynthesized from cortexolone; which is mediated by the enzyme 3-beta-HSD 1. In addition, 17alpha,21-Dihydroxypregnenolone can be biosynthesized from 17a-hydroxypregnenolone; which is catalyzed by the enzyme steroid 21-hydroxylase. In cattle, 17alpha,21-dihydroxypregnenolone is involved in the metabolic pathway called the steroidogenesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
17a,21-DihydroxypregnenoloneGenerator
17Α,21-dihydroxypregnenoloneGenerator
17alpha,21-Dihydroxypreg-nenoloneHMDB
17, 21-DihydroxypregnenoloneHMDB
3Β,17α,21-trihydroxypregnenoneHMDB
3beta,17alpha,21-TrihydroxypregnenoneHMDB
17,21-DihydroxypregnenoloneHMDB
3Β,17,21-trihydroxy-pregn-5-en-20-oneHMDB
3beta,17,21-Trihydroxy-pregn-5-en-20-oneHMDB
(3Β)-3,17,21-trihydroxypregn-5-en-20-oneHMDB
(3beta)-3,17,21-Trihydroxypregn-5-en-20-oneHMDB
3Β,17α,21-trihydroxypregn-5-en-20-oneHMDB
3beta,17alpha,21-Trihydroxypregn-5-en-20-oneHMDB
17alpha,21-DihydroxypregnenoloneHMDB
Chemical FormulaC21H32O4
Average Molecular Weight348.4764
Monoisotopic Molecular Weight348.230059512
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]-2-hydroxyethan-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]-2-hydroxyethanone
CAS Registry Number1167-48-2
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1
InChI KeyJNHJGXQUDOYJAK-IYRCEVNGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Oxosteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.6ALOGPS
logP2.02ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.86 m³·mol⁻¹ChemAxon
Polarizability39.63 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-4189000000-38652a1384b510a4e849View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f6t-1111090000-ac64327581e7c755d285View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0029000000-0868a1856a2a865dc2daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qa-0097000000-873e4eef53be76546e5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-0491000000-bf3679c3178ebe5ceb4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0029000000-5f642a89fae11d677fdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05bs-3098000000-d61819020861e0a89cf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6091000000-8a9828ddf7d9d4a69ef6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-b815dac004fdf0d56944View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kk-1096000000-5d0fda6d923e4716d986View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-a4cb9cce30a71598a761View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-4e7f285caeb4129cd706View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01xw-0911000000-08a13dee014c9e27e8d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00os-2930000000-32c88edb904f52d77158View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006762
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024065
KNApSAcK IDNot Available
Chemspider ID167253
KEGG Compound IDC05487
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound192735
PDB IDNot Available
ChEBI ID27832
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 11B1, mitochondrial
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in the biosynthesis of adrenal corticoids. Catalyzes the hydroxylation of carbon hydrogen bond at 11-beta position of 11-deoxycortisol and 11-deoxycorticosterone/21-hydroxyprogesterone yielding cortisol or corticosterone, respectively. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin).
Gene Name:
CYP11B1
Uniprot ID:
P15150
Molecular weight:
57847.0
Reactions
17a,21-Dihydroxypreg-nenolone + Oxygen + Reduced adrenal ferredoxin → 11b,17a,21-Trihydroxypreg-nenolone + Water + Oxidized adrenal ferredoxindetails