cis-coumarinic acid-β-D-glucoside (CHEM042152)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:52:44 UTC
Update Date2016-11-09 01:22:37 UTC
Accession NumberCHEM042152
Identification
Common Namecis-coumarinic acid-β-D-glucoside
ClassSmall Molecule
DescriptionA beta-D-glucoside consisting of cis-2-coumaric acid having a beta-D-glucosyl residue attached to the phenolic hydroxy group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylic acidChEBI
beta-D-Glucosyl-2-coumarinateChEBI
beta-D-Glucosyl-2-coumarinic acidChEBI
cis-beta-D-Glucosyl-2-hydroxycinnamic acidChEBI
cis-Coumarinic acid-beta-D-glucosideChEBI
cis-MelilotosideChEBI
(2Z)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylateGenerator
(2Z)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylic acidGenerator
(2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylateGenerator
(2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]acrylateGenerator
(2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]acrylic acidGenerator
cis-Coumarinate-β-D-glucosideGenerator
b-D-Glucosyl-2-coumarinateGenerator
b-D-Glucosyl-2-coumarinic acidGenerator
β-D-Glucosyl-2-coumarinateGenerator
β-D-Glucosyl-2-coumarinic acidGenerator
cis-b-D-Glucosyl-2-hydroxycinnamateGenerator
cis-b-D-Glucosyl-2-hydroxycinnamic acidGenerator
cis-beta-D-Glucosyl-2-hydroxycinnamateGenerator
cis-β-D-Glucosyl-2-hydroxycinnamateGenerator
cis-β-D-Glucosyl-2-hydroxycinnamic acidGenerator
cis-Coumarinate-b-D-glucosideGenerator
cis-Coumarinate-beta-D-glucosideGenerator
cis-Coumarinic acid-b-D-glucosideGenerator
cis-Coumarinic acid-β-D-glucosideGenerator
(2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acidHMDB
(2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acidHMDB
2'-(beta-D-Glucopyranosyloxy)cinnamic acidHMDB
2'-(β-D-Glucopyranosyloxy)cinnamic acidHMDB
2’-(β-D-Glucopyranosyloxy)cinnamic acidHMDB
3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acidHMDB
3-[2-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acidHMDB
Coumarin glucosideHMDB
Coumarinate glucosideHMDB
Coumarinic acid glucosideHMDB
beta-D-Glucosyl-2-coumarateHMDB
beta-D-Glucosyl-2-coumaric acidHMDB
cis-o-Hydroxycinnamic acid glucosideHMDB
o-(Glucosyloxy)cinnamic acidHMDB
o-Coumaroyl beta-D-glucopyranosideHMDB
o-Coumaroyl β-D-glucopyranosideHMDB
β-D-Glucosyl-2-coumarateHMDB
β-D-Glucosyl-2-coumaric acidHMDB
Chemical FormulaC15H18O8
Average Molecular Mass326.299 g/mol
Monoisotopic Mass326.100 g/mol
CAS Registry NumberNot Available
IUPAC Name(2Z)-3-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
Traditional Namecis-melilotoside
SMILESOC[C@H]1O[C@@H](OC2=CC=CC=C2\C=C/C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5-/t10-,12-,13+,14-,15-/m1/s1
InChI KeyGVRIYIMNJGULCZ-QLFWQTQQSA-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
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Styrene
  • Phenol ether
  • Phenoxy compound
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility6.6 g/LALOGPS
logP-0.7ALOGPS
logP-0.44ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.19 m³·mol⁻¹ChemAxon
Polarizability31.48 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-5943000000-c492ad4cea7748c10d1dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00di-1020229000-cd5e122c29a7c414bbb3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aos-0937000000-443e87b5dc30d11c2254Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-efd45bdfdb0cc42c2cb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-2900000000-be6e64ff24e527eb6506Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-0829000000-6df80077de9156a07096Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1911000000-4ab9ec4cd0e2b2cb4febSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0295-2900000000-78489653a0fdafbd5401Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00mk-0904000000-3dd34e382ba43fc1764fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0arr-0596000000-829180a1d0df8715f61cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2900000000-e9a87fed398fa7e220c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07f0-0598000000-7c06dab5e1ee09a3e269Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0j4i-1931000000-be23d1fceb38e06a6c84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-c4aef0c58740bba64b21Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDHMDB0060077
FooDB IDFDB030731
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-7417
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID22912899
ChEBI ID62251
PubChem Compound ID5316113
Kegg Compound IDC05839
YMDB IDNot Available
ECMDB IDM2MDB004461
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17421059
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17497625
3. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.