Record Information
Version1.0
Creation date2011-09-21 01:53:25 UTC
Update date2015-07-21 06:59:41 UTC
Primary IDFDB029293
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthurenate-8-O-beta-D-glucoside
DescriptionXanthurenic acid 8-O-beta-D-glucoside, a fluorescent metabolite, has been isolated from heads of eye-color mutants of Drosophila melanogaster. Only a few mutations cause it to accumulate, viz. cardinal (cd), dark red brown (drb), Henna-recessive (Hnr), purple (pr), Punch2 (Pu2), Punch-Grape (PuGr), and scarlet (st). After purification by ion-exchange chromatography, the spectroscopic, chemical, and enzymatic analyses revealed that it is a novel quinoline derivative. Feeding experiments suggest that this glucoside is synthesized from 3-hydroxykynurenine and that free xanthurenic acid is not a precursor. The results from the analysis for its occurrence in double mutants, together with the fact that xanthurenic acid 8-glucoside share the same precursor as xanthurenic acid and xanthommatin, suggest that xanthurenic acid 8-glucoside formation is closely related to the regulation of the last step in the biosynthesis of xanthommatin.[PMID: 3922986] Xanthurenic acid 8-glucoside is a side metabolite of the tryptophan-xanthommatin pathway in Drosophila. From 3-hydroxykynurenine, two biosynthetic pathways can be envisaged, one via xanthurenic acid, and another via 3-O-glucoside of 3-hydroxykynurenine. Evidence is presented to show that the synthesis takes place via xanthurenic acid. (a) the Drosophila melanogaster vermilion purple mutant (unable to synthesize 3-hydroxykynurenine) synthesizes xanthurenic acid 8-glucoside when fed with xanthurenic acid; and (b) the activities required for its synthesis via xanthurenic acid have been found (3-hydroxykynurenine transaminase and xanthurenic acid:UDP-glucosyltransferase). This is the first time that a UDP-glucosyltransferase activity that utilizes xanthurenic acid has been demonstrated. The enzyme in crude extracts from Drosophila sordidula shows the following characteristics. (a) It has optimal activity at 35 degrees C at pH 7.1 (in buffer Tris-HCl), and in the presence of a divalent cation (Mg2+ or Mn2+); (b) the activity is inhibited by xanthurenic acid (above 1.5 mM), UDP, D-gluconic acid 1,5-lactone, and Triton X-100; (c) it is localized in both the microsomal and the soluble fractions; (d) the specific activity is two times higher in heads than in bodies; and (e) the activity is enhanced in flies fed with phenobarbital. [HMDB]
CAS Number97451-32-6
Structure
Thumb
Synonyms
SynonymSource
Xanthurenate-8-O-b-D-glucosideGenerator
Xanthurenate-8-O-β-D-glucosideGenerator
Xanthurenic acid-8-O-b-D-glucosideGenerator
Xanthurenic acid-8-O-beta-D-glucosideGenerator
Xanthurenic acid-8-O-β-D-glucosideGenerator
4,8-Dihydroxy-8-O-beta-D-glucoside-quinaldic acid anionHMDB
4,8-Dihydroxy-8-O-beta-D-glucoside-quinoline-2-carboxylic acid anionHMDB
4,8-Dihydroxy-8-O-beta-delta-glucoside-quinaldic acid anionHMDB
4,8-Dihydroxy-8-O-beta-delta-glucoside-quinoline-2-carboxylic acid anionHMDB
4,8-Dihydroxyquinaldic acid 8-O-beta-D-glucosideHMDB
4,8-Dihydroxyquinaldic acid 8-O-beta-delta-glucosideHMDB
4,8-Dihydroxyquinoline-2-carboxylic acid 8-O-beta-D-glucosideHMDB
4,8-Dihydroxyquinoline-2-carboxylic acid 8-O-beta-delta-glucosideHMDB
Xan8GLCHMDB
Xanthurenic acid 8-O-beta-D-glucosideHMDB
Xanthurenic acid 8-O-beta-delta-glucosideHMDB
Xanthurenic acid 8-O-glucosideMeSH, HMDB
Cardinalic acidMeSH, HMDB
4-Hydroxy-8-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}quinoline-2-carboxylateGenerator
4,8-dihydroxy-8-O-beta-D-glucoside-quinaldic acid anionhmdb
4,8-dihydroxy-8-O-beta-D-glucoside-quinoline-2-carboxylic acid anionhmdb
4,8-dihydroxy-8-O-beta-delta-glucoside-quinaldic acid anionhmdb
4,8-dihydroxy-8-O-beta-delta-glucoside-quinoline-2-carboxylic acid anionhmdb
4,8-dihydroxyquinaldic acid 8-O-beta-D-glucosidehmdb
4,8-dihydroxyquinaldic acid 8-O-beta-delta-glucosidehmdb
4,8-dihydroxyquinoline-2-carboxylic acid 8-O-beta-D-glucosidehmdb
4,8-dihydroxyquinoline-2-carboxylic acid 8-O-beta-delta-glucosidehmdb
Xan8Glchmdb
xanthurenic acid 8-O-beta-D-glucosidehmdb
xanthurenic acid 8-O-beta-delta-glucosidehmdb
Predicted Properties
PropertyValueSource
Water Solubility5.1 g/LALOGPS
logP-0.41ALOGPS
logP-0.7ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.87ChemAxon
pKa (Strongest Basic)4.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area169.8 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.97 m³·mol⁻¹ChemAxon
Polarizability34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H17NO9
IUPAC name4-hydroxy-8-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}quinoline-2-carboxylic acid
InChI IdentifierInChI=1S/C16H17NO9/c18-5-10-12(20)13(21)14(22)16(26-10)25-9-3-1-2-6-8(19)4-7(15(23)24)17-11(6)9/h1-4,10,12-14,16,18,20-22H,5H2,(H,17,19)(H,23,24)/t10-,12+,13+,14+,16-/m1/s1
InChI KeyMYFHOUJDPFBJLH-XGJKELJWSA-N
Isomeric SMILESOC[C@H]1O[C@@H](OC2=C3N=C(C=C(O)C3=CC=C2)C(O)=O)[C@@H](O)[C@@H](O)[C@H]1O
Average Molecular Weight367.3075
Monoisotopic Molecular Weight367.090331147
Classification
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Quinoline-2-carboxylic acid
  • Hexose monosaccharide
  • Dihydroquinolone
  • O-glycosyl compound
  • Dihydroquinoline
  • Quinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Polyol
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSXanthurenate-8-O-beta-D-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uds-5926000000-404b2e8d5851ea309efdSpectrum
Predicted GC-MSXanthurenate-8-O-beta-D-glucoside, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-7332039000-350d78b17196c6d21ed5Spectrum
Predicted GC-MSXanthurenate-8-O-beta-D-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthurenate-8-O-beta-D-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0249000000-3063a43361b169d1e41aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1896000000-d0d6f5f037cf706f3de1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-114l-3940000000-01e636ec4d1c9981a108Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pvi-0259000000-8da58724f8100d50efd5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-0971000000-bd91a20ae5011a44f09bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06tr-2930000000-d907e683d10b2b2f124fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0219000000-18106fd97aab020dc8c2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-1339000000-5d4431e369fbcf176722Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r2-8950000000-8dbbaa9cf45b63a28a26Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0v4i-0109000000-919c5c092ea5bb4ed547Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0r00-2945000000-04f0431dc9dbf1f6e460Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-3920000000-43ce5a860e4fac9ebe25Spectrum
NMRNot Available
ChemSpider ID30776690
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481609
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13118
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference