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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:27:12 UTC
Update Date2022-03-07 02:54:31 UTC
HMDB IDHMDB0035461
Secondary Accession Numbers
  • HMDB35461
Metabolite Identification
Common NameYGM 3
DescriptionYGM 3 belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. YGM 3 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, YGM 3 has been detected, but not quantified in, cereals and cereal products and root vegetables. This could make YGM 3 a potential biomarker for the consumption of these foods.
Structure
Data?1563862723
SynonymsNot Available
Chemical FormulaC52H55O27
Average Molecular Weight1111.9769
Monoisotopic Molecular Weight1111.293071554
IUPAC Name2-(3,4-dihydroxyphenyl)-3-{[6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
Traditional Name2-(3,4-dihydroxyphenyl)-3-{[6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(\C=C\C(=O)OCC2OC(OC3C(OC4=C([O+]=C5C=C(O)C=C(OC6OC(CO)C(O)C(O)C6O)C5=C4)C4=CC(O)=C(O)C=C4)OC(COC(=O)\C=C\C4=CC(O)=C(O)C=C4)C(O)C3O)C(O)C(O)C2O)=C1
InChI Identifier
InChI=1S/C52H54O27/c1-70-33-13-22(3-8-28(33)57)5-11-39(61)71-19-36-41(63)44(66)47(69)51(77-36)79-49-45(67)42(64)37(20-72-38(60)10-4-21-2-7-26(55)29(58)12-21)78-52(49)75-34-17-25-31(73-48(34)23-6-9-27(56)30(59)14-23)15-24(54)16-32(25)74-50-46(68)43(65)40(62)35(18-53)76-50/h2-17,35-37,40-47,49-53,62-69H,18-20H2,1H3,(H5-,54,55,56,57,58,59,60,61)/p+1
InChI KeyCSWCMIODPBATKN-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 3-O-p-coumaroyl glycosides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.38ALOGPS
logP1.9ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area433.8 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity272.36 m³·mol⁻¹ChemAxon
Polarizability107.74 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+331.52730932474
DeepCCS[M-H]-329.80330932474
DeepCCS[M-2H]-363.83630932474
DeepCCS[M+Na]+337.85630932474
AllCCS[M+H]+301.732859911
AllCCS[M+H-H2O]+302.632859911
AllCCS[M+NH4]+300.832859911
AllCCS[M+Na]+300.532859911
AllCCS[M-H]-278.832859911
AllCCS[M+Na-2H]-284.232859911
AllCCS[M+HCOO]-290.132859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - YGM 3 10V, Positive-QTOFsplash10-03di-0900000000-99ff803b1da8d154683b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - YGM 3 20V, Positive-QTOFsplash10-03fr-1900000000-a242992982340cc06d9f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - YGM 3 40V, Positive-QTOFsplash10-03di-4900000000-47e302f24da9577a29242016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - YGM 3 10V, Negative-QTOFsplash10-03di-1900000000-fa583dd1ad047d1c7fa92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - YGM 3 20V, Negative-QTOFsplash10-03fr-2900000000-793596618d087b614cef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - YGM 3 40V, Negative-QTOFsplash10-052f-9200000000-572b0530d2040524aa422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - YGM 3 10V, Positive-QTOFsplash10-03dl-7900000003-bb3db9917e071ad95f522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - YGM 3 20V, Positive-QTOFsplash10-0ir1-5400002609-3520db5ae83c7acf3a272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - YGM 3 40V, Positive-QTOFsplash10-000j-0900000202-7a52a7605fd3d35a20292021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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
FooDB IDFDB014146
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751770
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
YGM 3 → 3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-({[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-yliumdetails