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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:56:32 UTC
Update Date2022-03-07 02:54:00 UTC
HMDB IDHMDB0034147
Secondary Accession Numbers
  • HMDB34147
Metabolite Identification
Common NameMonardaein
DescriptionMonardaein 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. Monardaein has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make monardaein a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Monardaein.
Structure
Data?1563862518
Synonyms
ValueSource
MonardeinHMDB
Chemical FormulaC42H41O23
Average Molecular Weight913.7611
Monoisotopic Molecular Weight913.203862618
IUPAC Name5-({5-[(2-carboxyacetyl)oxy]-6-{[(2-carboxyacetyl)oxy]methyl}-3,4-dihydroxyoxan-2-yl}oxy)-7-hydroxy-2-(4-hydroxyphenyl)-3-{[3,4,5-trihydroxy-6-({[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
Traditional Name5-({5-[(2-carboxyacetyl)oxy]-6-{[(2-carboxyacetyl)oxy]methyl}-3,4-dihydroxyoxan-2-yl}oxy)-7-hydroxy-2-(4-hydroxyphenyl)-3-{[3,4,5-trihydroxy-6-({[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
CAS Registry Number73545-87-6
SMILES
OC1C(COC(=O)\C=C/C2=CC=C(O)C=C2)OC(OC2=CC3=C(OC4OC(COC(=O)CC(O)=O)C(OC(=O)CC(O)=O)C(O)C4O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)C(O)C1O
InChI Identifier
InChI=1S/C42H40O23/c43-20-6-1-18(2-7-20)3-10-31(50)58-16-27-34(53)35(54)37(56)41(63-27)62-26-13-23-24(60-39(26)19-4-8-21(44)9-5-19)11-22(45)12-25(23)61-42-38(57)36(55)40(65-33(52)15-30(48)49)28(64-42)17-59-32(51)14-29(46)47/h1-13,27-28,34-38,40-42,53-57H,14-17H2,(H4-,43,44,45,46,47,48,49,50)/p+1
InChI KeyHOQNHEQPPFYHLF-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 Parents
Substituents
  • Flavonoid 3-o-6-p-coumaroyl-glycoside
  • Anthocyanidin-3-o-glycoside
  • Anthocyanidin-5-o-glycoside
  • Anthocyanin
  • Flavonoid-3-o-glycoside
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Pentacarboxylic acid or derivatives
  • Anthocyanidin
  • Phenolic glycoside
  • Coumaric acid ester
  • Cinnamic acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty acid ester
  • Fatty acyl
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Monocyclic benzene moiety
  • Oxane
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic cation
  • Aromatic heteropolycyclic compound
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 Solubility0.14 g/LALOGPS
logP2.52ALOGPS
logP2ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.94ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area365.4 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity218.96 m³·mol⁻¹ChemAxon
Polarizability86.07 ųChemAxon
Number of Rings6ChemAxon
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]+280.42430932474
DeepCCS[M-H]-278.24330932474
DeepCCS[M-2H]-312.20230932474
DeepCCS[M+Na]+286.64430932474
AllCCS[M+H]+275.032859911
AllCCS[M+H-H2O]+275.432859911
AllCCS[M+NH4]+274.632859911
AllCCS[M+Na]+274.532859911
AllCCS[M-H]-270.832859911
AllCCS[M+Na-2H]-275.632859911
AllCCS[M+HCOO]-281.032859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monardaein 10V, Positive-QTOFsplash10-01t9-0000000009-c365a0b6bcdfb90a3f442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monardaein 20V, Positive-QTOFsplash10-01t9-0000000039-a38f952ac9d27c252c822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monardaein 40V, Positive-QTOFsplash10-08i0-9800512135-2fc0f01fc2b0224ec6562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monardaein 10V, Negative-QTOFsplash10-03di-1000000009-77b94174baa8d852957c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monardaein 20V, Negative-QTOFsplash10-0r29-9400000027-7aba4ac475f07dff5bc62016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monardaein 40V, Negative-QTOFsplash10-0zfr-9600001000-cfb70b859ba27b45ca4c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monardaein 10V, Positive-QTOFsplash10-06r2-0431074294-b6b4f97b5e9bc07257cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monardaein 20V, Positive-QTOFsplash10-05ir-0320170391-232ab8a141d7106e07512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monardaein 40V, Positive-QTOFsplash10-066s-1950120140-a71f29c5ae14bc00fa212021-09-22Wishart 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 IDFDB012423
KNApSAcK IDC00057524
Chemspider ID3679934
KEGG Compound IDC08723
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4482008
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
Monardaein → {[6-({5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-7-hydroxy-2-(4-oxocyclohexa-2,5-dien-1-ylidene)-2H-chromen-3-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl}[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]oxidaniumdetails