Identification

Generic Name
Ergosterol
DrugBank Accession Number
DB04038
Background

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.

Type
Small Molecule
Groups
Approved, Experimental
Structure
Weight
Average: 396.659
Monoisotopic: 396.339216037
Chemical Formula
C28H44O
Synonyms
  • (22E,24S)-24-methylcholesta-5,7,22-trien-3β-ol
  • Provitamin D2

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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 acetate (2500 unit)TabletOralHall Laboratories, Ltd.1981-12-312003-09-11Canada flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-5-steroid / 3-hydroxy-delta-7-steroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Delta-5-steroid / Delta-7-steroid
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)
Affected organisms
Not Available

Chemical Identifiers

UNII
Z30RAY509F
CAS number
57-87-4
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
(1R,3aR,7S,9aR,9bS,11aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-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

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
KEGG Compound
C01694
PubChem Compound
444679
PubChem Substance
46505947
ChemSpider
392539
BindingDB
50378884
ChEBI
16933
ChEMBL
CHEMBL1232562
ZINC
ZINC000004084618
PDBe Ligand
ERG
Wikipedia
Ergosterol
PDB Entries
1bxm / 1zhz / 2aib / 5h2d / 5ys0 / 6cay / 6r4l / 6r4n / 6zzy / 7a4p
show 2 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability51.01 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

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52