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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-08 14:58:49 UTC
Update Date2021-09-14 14:57:23 UTC
HMDB IDHMDB0029175
Secondary Accession Numbers
  • HMDB29175
Metabolite Identification
Common Name3'-O-methyl-(-)-epicatechin
Description3'-O-methyl-(-)-epicatechin belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Based on a literature review very few articles have been published on 3'-O-methyl-(-)-epicatechin.
Structure
Data?1582753384
Synonyms
ValueSource
3'-O-MethylepicatechinMeSH, HMDB
Chemical FormulaC16H16O6
Average Molecular Weight304.2946
Monoisotopic Molecular Weight304.094688244
IUPAC Name(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Namesymplocosidin
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC=C1O)[C@H]1OC2=C(C[C@H]1O)C(O)=CC(O)=C2
InChI Identifier
InChI=1S/C16H16O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-6,13,16-20H,7H2,1H3/t13-,16-/m1/s1
InChI KeyNJHJXXLBWQXMRO-CZUORRHYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • 3p-methoxyflavonoid-skeleton
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
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 Solubility0.32 g/LALOGPS
logP1.3ALOGPS
logP1.94ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.48 m³·mol⁻¹ChemAxon
Polarizability30.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.72131661259
DarkChem[M-H]-176.28431661259
DeepCCS[M+H]+168.88430932474
DeepCCS[M-H]-166.52630932474
DeepCCS[M-2H]-200.78530932474
DeepCCS[M+Na]+176.88930932474
AllCCS[M+H]+172.032859911
AllCCS[M+H-H2O]+168.532859911
AllCCS[M+NH4]+175.432859911
AllCCS[M+Na]+176.332859911
AllCCS[M-H]-172.132859911
AllCCS[M+Na-2H]-171.732859911
AllCCS[M+HCOO]-171.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3'-O-methyl-(-)-epicatechinCOC1=CC(=CC=C1O)[C@H]1OC2=C(C[C@H]1O)C(O)=CC(O)=C24512.9Standard polar33892256
3'-O-methyl-(-)-epicatechinCOC1=CC(=CC=C1O)[C@H]1OC2=C(C[C@H]1O)C(O)=CC(O)=C22941.9Standard non polar33892256
3'-O-methyl-(-)-epicatechinCOC1=CC(=CC=C1O)[C@H]1OC2=C(C[C@H]1O)C(O)=CC(O)=C23077.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3'-O-methyl-(-)-epicatechin,1TMS,isomer #1COC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C1O[Si](C)(C)C2995.2Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,1TMS,isomer #2COC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O2994.8Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,1TMS,isomer #3COC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O)=CC=C1O2977.2Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,1TMS,isomer #4COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2O)=CC=C1O2999.7Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TMS,isomer #1COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2O)=CC=C1O[Si](C)(C)C2869.6Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TMS,isomer #2COC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O)=CC=C1O[Si](C)(C)C2854.3Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TMS,isomer #3COC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2897.0Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TMS,isomer #4COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O2824.0Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TMS,isomer #5COC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O2861.9Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TMS,isomer #6COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2O)=CC=C1O2878.7Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,3TMS,isomer #1COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2O)=CC=C1O[Si](C)(C)C2843.5Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,3TMS,isomer #2COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2754.2Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,3TMS,isomer #3COC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2773.2Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,3TMS,isomer #4COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O2795.1Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,4TMS,isomer #1COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2813.8Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,1TBDMS,isomer #1COC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C1O[Si](C)(C)C(C)(C)C3299.6Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,1TBDMS,isomer #2COC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O3306.1Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,1TBDMS,isomer #3COC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)=CC=C1O3247.3Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,1TBDMS,isomer #4COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C[C@H]2O)=CC=C1O3267.1Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TBDMS,isomer #1COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C[C@H]2O)=CC=C1O[Si](C)(C)C(C)(C)C3417.9Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TBDMS,isomer #2COC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)=CC=C1O[Si](C)(C)C(C)(C)C3395.3Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TBDMS,isomer #3COC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3442.0Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TBDMS,isomer #4COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O3362.1Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TBDMS,isomer #5COC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O3381.5Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,2TBDMS,isomer #6COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)=CC=C1O3399.2Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,3TBDMS,isomer #1COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)=CC=C1O[Si](C)(C)C(C)(C)C3558.9Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,3TBDMS,isomer #2COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3495.0Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,3TBDMS,isomer #3COC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3501.2Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,3TBDMS,isomer #4COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O3518.3Semi standard non polar33892256
3'-O-methyl-(-)-epicatechin,4TBDMS,isomer #1COC1=CC([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3690.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3'-O-methyl-(-)-epicatechin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-0970000000-6c633098c981f562bb092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-O-methyl-(-)-epicatechin GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1300090000-ee3f296bbddc7aa5e4912017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-O-methyl-(-)-epicatechin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 10V, Positive-QTOFsplash10-0a4r-0829000000-dce6600a87f5ea22cbf22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 20V, Positive-QTOFsplash10-000i-0910000000-48d37a8df6a8d67da2692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 40V, Positive-QTOFsplash10-00di-3900000000-b47131fd396ce6d24b132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 10V, Negative-QTOFsplash10-0udi-0109000000-d9f763fdb3d9d514c6822017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 20V, Negative-QTOFsplash10-0fri-0932000000-dcde0bacf216f37628082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 40V, Negative-QTOFsplash10-056r-1910000000-c4889d44d469442d15ef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 10V, Negative-QTOFsplash10-0udi-0009000000-04ccc09c7865adc860512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 20V, Negative-QTOFsplash10-0f79-0922000000-0105510e99e39b156b492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 40V, Negative-QTOFsplash10-0udr-1943000000-579c1bc20b033ef9a1ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 10V, Positive-QTOFsplash10-0a4i-0029000000-e08a393000273d238ca12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 20V, Positive-QTOFsplash10-052r-0923000000-e5ed677becc83090ef7c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-methyl-(-)-epicatechin 40V, Positive-QTOFsplash10-000i-2970000000-2c6005d292bc28820bdf2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 766 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029817
KNApSAcK IDNot Available
Chemspider ID9595142
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11420256
PDB IDNot Available
ChEBI ID70254
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 ReferencesNot Available