Record Information
Version1.0
Creation date2010-04-08 22:10:16 UTC
Update date2018-05-28 23:38:07 UTC
Primary IDFDB012612
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameErgosterol
DescriptionIndicator of fungal contamination, especies in cereals. Occurs in yeast and fungi. The main fungal steroidand is also found in small amts. in higher plant prods., e.g. palm oil [DFC].
CAS Number57-87-4
Structure
Thumb
Synonyms
SynonymSource
(22E)-Ergosta-5,7,22-trien-3-olbiospider
(22E)-Ergosta-5,7,22-trien-3beta-olbiospider
(24R)-Ergosta-5,7,22-trien-3b-olbiospider
(3β,22E)-Ergosta-5,7,22-trien-3-olbiospider
(3β)-Ergosta-5,7,22- trien-3-olbiospider
(3beta,22E)-Ergosta-5,7,22-trien-3-olbiospider
(3beta,2e)-Ergosta-5,7,22-trien-3-olHMDB
(3beta)-Ergosta-5,7,22-trien-3-olbiospider
24-Methylcholesta-5,7,22-trien-3b-olbiospider
24-Methylcholesta-5,7,22-trien-3beta-olbiospider
24a-Methyl-22E-dehydrocholesterolbiospider
24alpha-Methyl-22E-dehydrocholesterobiospider
24R-Methylcholesta-5,7,22E-trien-3b-olbiospider
24R-Methylcholesta-5,7,22E-trien-3beta-olbiospider
3beta-Hydroxy-5,7,22-ergostatrienebiospider
5,7,22-Ergostatrien-3beta-olbiospider
Ergosta-5,7,22-trien-3-olbiospider
Ergosterindb_source
Ergosteroldb_source
Ertrondb_source
Provitamin D2db_source
Provitamine D2biospider
Predicted Properties
PropertyValueSource
Water Solubility0.00016 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity127.13 m³·mol⁻¹ChemAxon
Polarizability49.5 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H44O
IUPAC name14-[(3E)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
InChI IdentifierInChI=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+
InChI KeyDNVPQKQSNYMLRS-BQYQJAHWSA-N
Isomeric SMILESCC(C)C(C)\C=C\C(C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C
Average Molecular Weight396.6484
Monoisotopic Molecular Weight396.33921603
Classification
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 Parents
Substituents
  • Ergosterol-skeleton
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxy-delta-5-steroid
  • Delta-7-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 84.79%; H 11.18%; O 4.03%DFC
Melting PointMp 168° (165°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -133 (CHCl3)DFC
Spectroscopic UV Data293 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1019000000-9682b479cb367468e4f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ss-6149000000-8fcdb7198ebd094e3658View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-9085000000-b5f06c3d8a32fea4fc08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-36b82459f90e5096bbffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-17e94d8c42f8b29d1d7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3019000000-d968e794cb4f844efc59View in MoNA
ChemSpider ID10477914
ChEMBL IDNot Available
KEGG Compound IDC01694
Pubchem Compound ID21775588
Pubchem Substance IDNot Available
ChEBI ID16933
Phenol-Explorer IDNot Available
DrugBank IDDB04038
HMDB IDHMDB00878
CRC / DFC (Dictionary of Food Compounds) IDNXR27-J:HJJ37-Q
EAFUS IDNot Available
Dr. Duke IDERGOSTEROL|7-ERGOSTEROL
BIGG IDNot Available
KNApSAcK IDC00003652
HET ID1BXM
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDErgosterol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.