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Showing Compound Pregnenolone (FDB021920)

Record Information
Version1.0
Creation date2011-09-21 00:05:11 UTC
Update date2019-11-26 03:21:00 UTC
Primary IDFDB021920
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePregnenolone
DescriptionPregnenolone is a derivative of cholesterol, the product of Cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1); this reaction consists of three consecutive monooxygenations; a 22-hydroxylation, 20-hydroxylation and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted to pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and transport to the inner membrane steps and thus to exerts a powerful control over the use of cholesterol for aldosterone production. (PMID: 17222962, 15823613, 16632873, 15134809) [HMDB]. Pregnenolone is found in many foods, some of which are common wheat, yellow bell pepper, oval-leaf huckleberry, and fenugreek.
CAS Number145-13-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3b)-3-Hydroxy-pregn-5-en-20-oneHMDB
3-Hydroxypregn-5-en-20-oneHMDB
3b-Hydroxypregn-5-en-20-oneHMDB
3beta-Hydroxypregn-5-en-20-oneHMDB
5-Pregnen-3b-ol-20-oneHMDB
5-Pregnen-3beta-ol-20-oneHMDB
NatoloneHMDB
Pregn-5-en-3b-ol-20-oneHMDB
Pregn-5-ene-3b-ol-20-oneHMDB
PregnetanHMDB
PregnetonHMDB
PregnolonHMDB
PrenolonHMDB
RegnosoneHMDB
SkinostelonHMDB
(3b)-3-hydroxy-Pregn-5-en-20-onehmdb
3-hydroxypregn-5-en-20-onehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.06ALOGPS
logP3.58ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.76 m³·mol⁻¹ChemAxon
Polarizability37.91 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H32O2
IUPAC name1-[(1S,2R,5R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
InChI IdentifierInChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16?,17-,18+,19+,20+,21-/m1/s1
InChI KeyORNBQBCIOKFOEO-STZXPNGSSA-N
Isomeric SMILES[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])C2CC=C2C[C@H](O)CC[C@]12C
Average Molecular Weight316.4776
Monoisotopic Molecular Weight316.240230268
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-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPregnenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pic-0291000000-ac74781c70d5d5a7095cSpectrum
Predicted GC-MSPregnenolone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-2139000000-4638ad03d702bd6d4f0bSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0195000000-742fffef9b8fa170f05e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0391000000-7f19b3f9aed012b1e5392016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbo-3390000000-f6f0115bbcd9afb5ddb92016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0039000000-5c36ec019f325626a9b62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0089000000-99239f61c3086ee3d4342016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0592-1090000000-66cb81b0a398e104af3c2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01953
Pubchem Compound ID53477678
Pubchem Substance IDNot Available
ChEBI ID16581
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00253
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID38769
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPregnenolone
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
Sulfotransferase family cytosolic 2B member 1SULT2B1O00204
Cytochrome P450, family 21, subfamily A, polypeptide 2CYP21A2Q08AG9
Cytochrome P450 21-hydroxylaseP450-CYP21BQ16874
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130 map00140
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference