Showing metabocard for Ergosterol (BMDB0000878)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:37:58 UTC
Update Date2020-04-22 15:05:45 UTC
BMDB IDBMDB0000878
Secondary Accession Numbers
  • BMDB00878
Metabolite Identification
Common NameErgosterol
DescriptionXanthurenic acid, also known as xanthurenate or 8-hydroxykynurenate, belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Xanthurenic acid is a very strong basic compound (based on its pKa). Xanthurenic acid exists in all living species, ranging from bacteria to humans. In cattle, xanthurenic acid is involved in the metabolic pathway called the tryptophan metabolism pathway. Xanthurenic acid, with regard to humans, has been found to be associated with several diseases such as hemodialysis, colorectal cancer, and eosinophilic esophagitis; xanthurenic acid has also been linked to the inborn metabolic disorder kynureninase deficiency.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
XanthurenateKegg
8-Hydroxykynurenic acidHMDB
Gametocyte activating factor (gaf)HMDB
4,8-Dihydroxy-2-quinolinecarboxylateHMDB
4,8-Dihydroxy-2-quinolinecarboxylic acidHMDB
4,8-Dihydroxy-quinaldateHMDB
4,8-Dihydroxy-quinaldic acidHMDB
4,8-DihydroxyquinaldateHMDB
4,8-Dihydroxyquinaldic acidHMDB
4,8-DihydroxyquinaldinateHMDB
4,8-Dihydroxyquinaldinic acidHMDB
4,8-Dihydroxyquinoline-2-carboxylateHMDB
4,8-Dihydroxyquinoline-2-carboxylic acidHMDB
4-Oxoxanthurenic acidHMDB
8-HydroxykynurenateHMDB
OxoxanthurenateHMDB
XanthurateHMDB
Xanthuric acidHMDB
(22E)-Ergosta-5,7,22-trien-3-olHMDB
(24R)-Ergosta-5,7,22-trien-3b-olHMDB
(3beta)-Ergosta-5,7,22-trien-3-olHMDB
(3beta,22E)-Ergosta-5,7,22-trien-3-olHMDB
(3beta,2E)-Ergosta-5,7,22-trien-3-olHMDB
24-Methylcholesta-5,7,22-trien-3b-olHMDB
24-Methylcholesta-5,7,22-trien-3beta-olHMDB
24a-Methyl-22E-dehydrocholesterolHMDB
24alpha-Methyl-22E-dehydrocholesteroHMDB
24R-Methylcholesta-5,7,22E-trien-3b-olHMDB
24R-Methylcholesta-5,7,22E-trien-3beta-olHMDB
Ergosta-5,7,22-trien-3-olHMDB
ErgosterinHMDB
Provitamine D2HMDB
Chemical FormulaC28H44O
Average Molecular Weight396.6484
Monoisotopic Molecular Weight396.33921603
IUPAC Name(2R,5S,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
Traditional Name(2R,5S,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
CAS Registry Number57-87-4
SMILES
CC(C)[C@@H](C)\C=C\[C@@H](C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
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
InChI KeyDNVPQKQSNYMLRS-KQYMERMZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-2-carboxylic acid
  • Dihydroquinolone
  • Hydroxyquinoline
  • 8-hydroxyquinoline
  • Dihydroquinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility16 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability49.94 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fsi-1019000000-1eb795b4071c3dc0a42cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udl-2003900000-c84feed3f7fbf11526ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0009000000-ca7841e724086fd88a01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05us-5891000000-5675b1af0ce9ff87b1a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000x-5920000000-6eca7b0791c4a09fb2e8View in MoNA
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
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000881
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022297
KNApSAcK IDNot Available
Chemspider ID5497
KEGG Compound IDC02470
BioCyc IDXANTHURENATE
BiGG IDNot Available
Wikipedia LinkXanthurenic_acid
METLIN ID5841
PubChem Compound5699
PDB IDNot Available
ChEBI ID10072
References
Synthesis ReferenceHe, Xiuping; Zhang, Borun; Tan, Huarong. Overexpression of a sterol C-24(28) reductase increases ergosterol production in Saccharomyces cerevisiae. Biotechnology Letters (2003), 25(10), 773-778.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available