Ergosterol

Identification

Name
Ergosterol
Accession Number
DB04038  (EXPT01357)
Type
Small Molecule
Groups
Approved, Experimental
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
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Zoo Chews Plus IronErgosterol (400 unit) + Ascorbic acid (50 mg) + Cyanocobalamin (4.5 mcg) + DL-alpha tocopheryl acetate (15 unit) + Ferrous fumarate (4 mg) + Folic Acid (.3 mg) + Nicotinamide (13.5 mg) + Pyridoxine hydrochloride (1.05 mg) + Riboflavin (1.2 mg) + Sodium ascorbate (10 mg) + Thiamine mononitrate (1.05 mg) + Vitamin A (2500 unit)TabletOralHall Laboratories, Ltd.1981-12-312003-09-11Canada
Categories
UNII
Z30RAY509F
CAS number
57-87-4
Weight
Average: 396.659
Monoisotopic: 396.339216037
Chemical Formula
C28H44O
InChI Key
DNVPQKQSNYMLRS-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)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Cholesterol Biosynthesis and MetabolismMetabolic
Steroid Biosynthesis Metabolic
Cholesterol Biosynthesis and Metabolism CE(10:0)Metabolic
Cholesterol Biosynthesis and Metabolism CE(12:0)Metabolic
Cholesterol Biosynthesis and Metabolism CE(14:0)Metabolic
Cholesterol Biosynthesis and Metabolism CE(16:0)Metabolic
Cholesterol Biosynthesis and Metabolism CE(18:0)Metabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
KEGG Compound
C01694
PubChem Compound
444679
PubChem Substance
46505947
ChemSpider
392539
BindingDB
50378884
ChEBI
16933
ChEMBL
CHEMBL1232562
HET
ERG
Wikipedia
Ergosterol
PDB Entries
1bxm / 1zhz / 2aib / 5h2d / 5ys0 / 6cay

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0536-2911000000-0f3a53ac2076470e08fd
Mass Spectrum (Electron Ionization)MSsplash10-07bg-6943000000-5fbc1f7b29d046df3944
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Ergostane steroids
Direct Parent
Ergosterols and derivatives
Alternative Parents
3-hydroxy delta-7-steroids / 3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-7-steroids / Delta-5-steroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Ergosterol-skeleton / 3-hydroxy-delta-5-steroid / 3-hydroxy-delta-7-steroid / 3-hydroxysteroid / Hydroxysteroid / 3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / Delta-7-steroid / Delta-5-steroid / Cyclic alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3beta-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 November 02, 2018 05:48