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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:52:52 UTC
Update Date2019-07-23 07:13:33 UTC
HMDB IDHMDB0060077
Secondary Accession Numbers
  • HMDB60077
Metabolite Identification
Common Namecis-beta-D-Glucosyl-2-hydroxycinnamate
DescriptionThis compound belongs to the family of O-glycosyl Compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
Structure
Data?1563866013
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
Chemical FormulaC15H18O8
Average Molecular Weight326.2986
Monoisotopic Molecular Weight326.100167552
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
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=CC=CC=C2\C=C/C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=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
DescriptionThis compound 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
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Polarizability30.89 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-5943000000-c492ad4cea7748c10d1dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00di-1020229000-cd5e122c29a7c414bbb3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aos-0937000000-443e87b5dc30d11c2254JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-efd45bdfdb0cc42c2cb9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-2900000000-be6e64ff24e527eb6506JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-0829000000-6df80077de9156a07096JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1911000000-4ab9ec4cd0e2b2cb4febJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0295-2900000000-78489653a0fdafbd5401JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030731
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05839
BioCyc IDCPD-7417
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5316113
PDB IDNot Available
ChEBI ID62251
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:23455439 ]

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
cis-beta-D-Glucosyl-2-hydroxycinnamate + Water → 4-Hydroxycinnamic acid + D-Glucosedetails