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Identification
NamePregnenolone
Accession NumberDB02789  (EXPT02608)
TypeSmall Molecule
GroupsExperimental
Description

A 21-carbon steroid, derived from CHOLESTEROL and found in steroid hormone-producing tissues. Pregnenolone is the precursor to GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS. [PubChem]

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII73R90F7MQ8
CAS numberNot Available
WeightAverage: 316.4776
Monoisotopic: 316.240230268
Chemical FormulaC21H32O2
InChI KeyInChIKey=ORNBQBCIOKFOEO-QGVNFLHTSA-N
InChI
InChI=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+/m0/s1
IUPAC Name
1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O
Taxonomy
DescriptionThis compound 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-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Pregnenolone
Not Available
17-Hydroxypregnenolone sulfateDetails
Pregnenolone
Not Available
Pregnenolone sulfateDetails
Pregnenolone
Not Available
3beta-Hydroxypregn-5-en-20-one sulfateDetails
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9671
Caco-2 permeable+0.8568
P-glycoprotein substrateSubstrate0.6106
P-glycoprotein inhibitor IInhibitor0.6721
P-glycoprotein inhibitor IINon-inhibitor0.7531
Renal organic cation transporterNon-inhibitor0.7825
CYP450 2C9 substrateNon-substrate0.8333
CYP450 2D6 substrateNon-substrate0.8417
CYP450 3A4 substrateSubstrate0.7594
CYP450 1A2 substrateNon-inhibitor0.9179
CYP450 2C9 inhibitorNon-inhibitor0.9333
CYP450 2D6 inhibitorNon-inhibitor0.9558
CYP450 2C19 inhibitorNon-inhibitor0.9023
CYP450 3A4 inhibitorNon-inhibitor0.8332
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9076
Ames testNon AMES toxic0.9439
CarcinogenicityNon-carcinogens0.9346
BiodegradationNot ready biodegradable0.9379
Rat acute toxicity1.9852 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8779
hERG inhibition (predictor II)Non-inhibitor0.7239
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0136 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.76 m3·mol-1ChemAxon
Polarizability38.05 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0fic-5910000000-4b4de0891180a420522aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-6920000000-2b11c86505b10fe4485fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
Synthesis Reference

Alexander James Bridges, “Efficient Process for Preparing Steroids and Vitamin D Derivatives With the Unnatural Configuration at C20 (20 Alpha-Methyl) from Pregnenolone.” U.S. Patent US20080171728, issued July 17, 2008.

US20080171728
General References
  1. Geyer J, Doring B, Meerkamp K, Ugele B, Bakhiya N, Fernandes CF, Godoy JR, Glatt H, Petzinger E: Cloning and functional characterization of human sodium-dependent organic anion transporter (SLC10A6). J Biol Chem. 2007 Jul 6;282(27):19728-41. Epub 2007 May 9. [PubMed:17491011 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Steroid sulfotransferase activity
Specific Function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. I...
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular Weight:
41307.32 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-dependent organic anion transmembrane transporter activity
Specific Function:
Transports sulfoconjugated steroid hormones, as well as taurolithocholic acid-3-sulfate and sulfoconjugated pyrenes in a sodium-dependent manner.
Gene Name:
SLC10A6
Uniprot ID:
Q3KNW5
Molecular Weight:
41258.24 Da
References
  1. Geyer J, Doring B, Meerkamp K, Ugele B, Bakhiya N, Fernandes CF, Godoy JR, Glatt H, Petzinger E: Cloning and functional characterization of human sodium-dependent organic anion transporter (SLC10A6). J Biol Chem. 2007 Jul 6;282(27):19728-41. Epub 2007 May 9. [PubMed:17491011 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:19