cyclo-dopa 5-O-glucoside (CHEM042178)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:53:52 UTC
Update Date2016-11-09 01:22:37 UTC
Accession NumberCHEM042178
Identification
Common Namecyclo-dopa 5-O-glucoside
ClassSmall Molecule
DescriptionAn indolyl carbohydrate that is cyclodopa in which the phenolic hydrogen at position 5 has been replaced by a beta-D-glucosyl residue.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Cyclo-dopa 5-O-glucosideChEBI
Cyclodopa glucosideChEBI
Leucodopachrome 5-beta-D-glucosideChEBI
Leucodopachrome glucosideChEBI
Leucodopachrome 5-b-D-glucosideGenerator
Leucodopachrome 5-β-D-glucosideGenerator
Cyclodopa 5-b-D-glucosideGenerator
Cyclodopa 5-β-D-glucosideGenerator
Chemical FormulaC15H19NO9
Average Molecular Mass357.315 g/mol
Monoisotopic Mass357.106 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S)-6-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-indole-2-carboxylic acid
Traditional Name(2S)-6-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-indole-2-carboxylic acid
SMILES[H][C@]1(CC2=CC(O[C@]3([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]3([H])O)=C(O)C=C2N1)C(O)=O
InChI IdentifierInChI=1S/C15H19NO9/c17-4-10-11(19)12(20)13(21)15(25-10)24-9-2-5-1-7(14(22)23)16-6(5)3-8(9)18/h2-3,7,10-13,15-21H,1,4H2,(H,22,23)/t7-,10+,11+,12-,13+,15+/m0/s1
InChI KeyPXMFPPFHRQZIHO-OLCQZNMOSA-N
Chemical Taxonomy
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
  • Indolecarboxylic acid derivative
  • Indolecarboxylic acid
  • Hexose monosaccharide
  • O-glycosyl compound
  • Alpha-amino acid
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Indole or derivatives
  • Dihydroindole
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Amino acid
  • Secondary alcohol
  • Amino acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Organonitrogen 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 Solubility27.5 g/LALOGPS
logP-0.92ALOGPS
logP-2.9ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)4.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area168.94 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity81.5 m³·mol⁻¹ChemAxon
Polarizability33.85 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054n-0907000000-ff945066b5dac54a8851Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0092-0900000000-9f1c2cdc65b45467ccb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-0900000000-ca869b2f092a2bb9a36dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-0719000000-647a4cd4f5968af93fd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1912000000-641aa4739b3647c5c79eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-2900000000-81ef127f679a51a2e92cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-0904000000-6b9bd6edba3a4a0de741Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-c5b4821a801403a2095cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k95-3940000000-6e1aff2ef0b4bc6428a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0409000000-805787cb1e9657ecdc29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6w-0911000000-c480ac2d6e13f0464653Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-0900000000-fc7bd783bfc0525f45d6Spectrum
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 IDHMDB0304310
FooDB IDFDB030765
Phenol Explorer IDNot Available
KNApSAcK IDC00053126
BiGG IDNot Available
BioCyc IDCPD-8656
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30791580
ChEBI ID134458
PubChem Compound ID46173990
Kegg Compound IDC17751
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11421447