Ergosterol (CHEM028339)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:23:21 UTC
Update Date2016-11-09 01:18:40 UTC
Accession NumberCHEM028339
Identification
Common NameErgosterol
ClassSmall Molecule
DescriptionA quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical 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 Mass396.648 g/mol
Monoisotopic Mass396.339 g/mol
CAS Registry Number57-87-4
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
SMILESCC(C)C(C)\C=C\C(C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability49.94 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fsi-1019000000-1eb795b4071c3dc0a42cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udl-2003900000-c84feed3f7fbf11526ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0009000000-ca7841e724086fd88a01Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05us-5891000000-5675b1af0ce9ff87b1a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000x-5920000000-6eca7b0791c4a09fb2e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1019000000-9682b479cb367468e4f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ss-6149000000-8fcdb7198ebd094e3658Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-9085000000-b5f06c3d8a32fea4fc08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-36b82459f90e5096bbffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-17e94d8c42f8b29d1d7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3019000000-d968e794cb4f844efc59Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000881
FooDB IDFDB022297
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDXANTHURENATE
METLIN ID5841
PDB IDNot Available
Wikipedia LinkXanthurenic_acid
Chemspider ID5497
ChEBI ID10072
PubChem Compound ID5699
Kegg Compound IDC02470
YMDB IDYMDB01807
ECMDB IDM2MDB004569
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11045716
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20617247
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21188174
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22036934
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22491023
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22701629
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23139790
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23303071
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=4614128
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=4886323
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=8598102
13. Furst, Arthur; Olsen, Carl J. A convenient synthesis of xanthurenic acid. Journal of Organic Chemistry (1951), 16 412-14.
14. Furst, Arthur; Olsen, Carl J. A convenient synthesis of xanthurenic acid. Journal of Organic Chemistry (1951), 16 412-14.
15. Bapurao S, Krishnaswamy K: Vitamin B6 nutritional status of pellagrins and their leucine tolerance. Am J Clin Nutr. 1978 May;31(5):819-24.
16. Shibata K, Fukuwatari T, Murakami M, Sasaki R: Increase in conversion of tryptophan to niacin in pregnant rats. Adv Exp Med Biol. 2003;527:435-41.
17. Forrest CM, Gould SR, Darlington LG, Stone TW: Levels of purine, kynurenine and lipid peroxidation products in patients with inflammatory bowel disease. Adv Exp Med Biol. 2003;527:395-400.
18. Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60.
19. Hoes MJ, Loeffen T, Vree TB: Kinetics of L-tryptophan in depressive patients: a possible correlation between the plasma concentrations of L-tryptophan and some psychiatric rating scales. Psychopharmacology (Berl). 1981;75(4):350-3.
20. Malina HZ, Hess OM: Xanthurenic acid translocates proapoptotic Bcl-2 family proteins into mitochondria and impairs mitochondrial function. BMC Cell Biol. 2004 Apr 6;5:14.
21. Bapurao S, Raman L, Tulpule PG: Biochemical assessment of vitamin B6 nutritional status in pregnant women with orolingual manifestations. Am J Clin Nutr. 1982 Oct;36(4):581-6.
22. Malina HZ: Comment on 'The photosensitiser xanthurenic acid is not present in normal human lenses' by P.G. Hains et al. [Exp. Eye Res. 77 (2003) 547-553]. Exp Eye Res. 2004 Sep;79(3):443-5; author reply 447-8.
23. Forrest CM, Kennedy A, Stone TW, Stoy N, Darlington LG: Kynurenine and neopterin levels in patients with rheumatoid arthritis and osteoporosis during drug treatment. Adv Exp Med Biol. 2003;527:287-95.
24. Igari T, Tsuchizawa M, Shimamura T: Alteration of tryptophan metabolism in the synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Tohoku J Exp Med. 1987 Oct;153(2):79-86.