Identification
NameErgosterol
Accession NumberDB04038  (EXPT01357)
TypeSmall Molecule
GroupsExperimental
Description

A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL.

Structure
Thumb
Synonyms
(22E,24S)-24-methylcholesta-5,7,22-trien-3β-ol
Provitamin D2
External IDs Not Available
Product Ingredients 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
Categories
UNIIZ30RAY509F
CAS number57-87-4
WeightAverage: 396.659
Monoisotopic: 396.339216037
Chemical FormulaC28H44O
InChI KeyDNVPQKQSNYMLRS-APGDWVJJSA-N
InChI
InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
IUPAC Name
(1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
SMILES
CC(C)[C@@H](C)\C=C\[C@@H](C)[[email protected]]1CC[[email protected]]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[[email protected]]3CC[C@]12C
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis Reference

Nina Vasilievna Tarasova, Elena Abramovna Obolnikova, Alexandr Dmitrievich Gololobov, Gleb Ivanovich Samokhvalov, Sergei Vladimirovich Chepigo, Galina Ivanovna Ivanova, Vladimir Vasilievich Imshenetsky, Vera Mikhailovna Kulikova, "Method for preparing ergosterol and ubiquinone-9 in a single process." U.S. Patent US3965130, issued October, 1961.

US3965130
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)170 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.000156 mg/mLALOGPS
logP7.39ALOGPS
logP6.63ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity127.13 m3·mol-1ChemAxon
Polarizability50.29 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9642
Caco-2 permeable+0.8165
P-glycoprotein substrateSubstrate0.6394
P-glycoprotein inhibitor IInhibitor0.6449
P-glycoprotein inhibitor IINon-inhibitor0.8338
Renal organic cation transporterNon-inhibitor0.7839
CYP450 2C9 substrateNon-substrate0.8308
CYP450 2D6 substrateNon-substrate0.8645
CYP450 3A4 substrateSubstrate0.7483
CYP450 1A2 substrateNon-inhibitor0.914
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9478
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8916
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7895
Ames testNon AMES toxic0.9231
CarcinogenicityNon-carcinogens0.9287
BiodegradationNot ready biodegradable0.9623
Rat acute toxicity2.6528 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8502
hERG inhibition (predictor II)Non-inhibitor0.7488
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0536-2911000000-0f3a53ac2076470e08fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-07bg-6943000000-5fbc1f7b29d046df3944View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents3-beta-hydroxysteroids / 3-beta-hydroxy-delta-7-steroids / 3-beta-hydroxy delta-5-steroids / Delta-7-steroids / Delta-5-steroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
SubstituentsErgosterol-skeleton / 3-beta-hydroxy-delta-7-steroid / 3-beta-hydroxysteroid / 3-beta-hydroxy-delta-5-steroid / Hydroxysteroid / 3-hydroxysteroid / 3-hydroxy-delta-7-steroid / 3-hydroxy-delta-5-steroid / Delta-7-steroid / Delta-5-steroid
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors3beta-sterol, ergostanoid, phytosterols (CHEBI:16933 ) / Ergosterols and C24-methyl derivatives, Vitamin D2 and derivatives, Ergostane and derivatives (C01694 ) / Ergosterols and C24-methyl derivatives (LMST01030093 )
Drug created on June 13, 2005 07:24 / Updated on June 11, 2017 20:52