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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:11:45 UTC
Update Date2022-03-07 02:57:02 UTC
HMDB IDHMDB0041507
Secondary Accession Numbers
  • HMDB41507
Metabolite Identification
Common Name3'-O-Methylcatechin
Description3'-O-Methylcatechin, also known as 3-MTHF or meciadanol, 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-Methylcatechin.
Structure
Data?1563863671
Synonyms
ValueSource
3-O-MethylcatechinHMDB
3-MTHFHMDB
3-O-Methylcatechin, (2R-trans)-isomerHMDB
3',4',5,7-Tetrahydroxy-3-methoxyflavanHMDB
2-Methoxy-5,7,3',4'-tetrahydroxyflavanHMDB
3-O-Methyl-(+)-catechinHMDB
3’-O-methylcatechinHMDB
MeciadanolHMDB
3'-O-MethylcatechinMeSH
Chemical FormulaC16H16O6
Average Molecular Weight304.298
Monoisotopic Molecular Weight304.094688235
IUPAC Name(2R,3S)-2-(3,4-dihydroxyphenyl)-3-methoxy-3,4-dihydro-2H-1-benzopyran-5,7-diol
Traditional Name(2R,3S)-2-(3,4-dihydroxyphenyl)-3-methoxy-3,4-dihydro-2H-1-benzopyran-5,7-diol
CAS Registry Number65350-86-9
SMILES
CO[C@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C=C(O)C=C2O
InChI Identifier
InChI=1S/C16H16O6/c1-21-15-7-10-12(19)5-9(17)6-14(10)22-16(15)8-2-3-11(18)13(20)4-8/h2-6,15-20H,7H2,1H3/t15-,16+/m0/s1
InChI KeyPDHSAQOQVUXZGQ-JKSUJKDBSA-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
  • 3-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility0.32 g/LALOGPS
logP1.68ALOGPS
logP2.44ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.75 m³·mol⁻¹ChemAxon
Polarizability30.93 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
DeepCCS[M+H]+168.23130932474
DeepCCS[M-H]-165.87430932474
DeepCCS[M-2H]-199.89430932474
DeepCCS[M+Na]+175.12130932474
AllCCS[M+H]+171.432859911
AllCCS[M+H-H2O]+168.232859911
AllCCS[M+NH4]+174.432859911
AllCCS[M+Na]+175.232859911
AllCCS[M-H]-170.032859911
AllCCS[M+Na-2H]-169.532859911
AllCCS[M+HCOO]-169.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3'-O-MethylcatechinCO[C@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C=C(O)C=C2O4359.0Standard polar33892256
3'-O-MethylcatechinCO[C@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C=C(O)C=C2O2940.5Standard non polar33892256
3'-O-MethylcatechinCO[C@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C=C(O)C=C2O3076.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3'-O-Methylcatechin,1TMS,isomer #1CO[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O[Si](C)(C)C)=C12954.8Semi standard non polar33892256
3'-O-Methylcatechin,1TMS,isomer #2CO[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O[Si](C)(C)C)C(O)=C12953.9Semi standard non polar33892256
3'-O-Methylcatechin,1TMS,isomer #3CO[C@H]1CC2=C(O)C=C(O[Si](C)(C)C)C=C2O[C@@H]1C1=CC=C(O)C(O)=C12924.5Semi standard non polar33892256
3'-O-Methylcatechin,1TMS,isomer #4CO[C@H]1CC2=C(C=C(O)C=C2O[Si](C)(C)C)O[C@@H]1C1=CC=C(O)C(O)=C12912.2Semi standard non polar33892256
3'-O-Methylcatechin,2TMS,isomer #1CO[C@H]1CC2=C(C=C(O)C=C2O[Si](C)(C)C)O[C@@H]1C1=CC=C(O)C(O[Si](C)(C)C)=C12828.4Semi standard non polar33892256
3'-O-Methylcatechin,2TMS,isomer #2CO[C@H]1CC2=C(O)C=C(O[Si](C)(C)C)C=C2O[C@@H]1C1=CC=C(O)C(O[Si](C)(C)C)=C12832.2Semi standard non polar33892256
3'-O-Methylcatechin,2TMS,isomer #3CO[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12856.2Semi standard non polar33892256
3'-O-Methylcatechin,2TMS,isomer #4CO[C@H]1CC2=C(C=C(O)C=C2O[Si](C)(C)C)O[C@@H]1C1=CC=C(O[Si](C)(C)C)C(O)=C12819.4Semi standard non polar33892256
3'-O-Methylcatechin,2TMS,isomer #5CO[C@H]1CC2=C(O)C=C(O[Si](C)(C)C)C=C2O[C@@H]1C1=CC=C(O[Si](C)(C)C)C(O)=C12819.7Semi standard non polar33892256
3'-O-Methylcatechin,2TMS,isomer #6CO[C@H]1CC2=C(C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)O[C@@H]1C1=CC=C(O)C(O)=C12780.3Semi standard non polar33892256
3'-O-Methylcatechin,3TMS,isomer #1CO[C@H]1CC2=C(C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)O[C@@H]1C1=CC=C(O)C(O[Si](C)(C)C)=C12828.6Semi standard non polar33892256
3'-O-Methylcatechin,3TMS,isomer #2CO[C@H]1CC2=C(C=C(O)C=C2O[Si](C)(C)C)O[C@@H]1C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12793.0Semi standard non polar33892256
3'-O-Methylcatechin,3TMS,isomer #3CO[C@H]1CC2=C(O)C=C(O[Si](C)(C)C)C=C2O[C@@H]1C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12791.0Semi standard non polar33892256
3'-O-Methylcatechin,3TMS,isomer #4CO[C@H]1CC2=C(C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)O[C@@H]1C1=CC=C(O[Si](C)(C)C)C(O)=C12813.5Semi standard non polar33892256
3'-O-Methylcatechin,4TMS,isomer #1CO[C@H]1CC2=C(C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)O[C@@H]1C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12857.7Semi standard non polar33892256
3'-O-Methylcatechin,1TBDMS,isomer #1CO[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13246.5Semi standard non polar33892256
3'-O-Methylcatechin,1TBDMS,isomer #2CO[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C13250.8Semi standard non polar33892256
3'-O-Methylcatechin,1TBDMS,isomer #3CO[C@H]1CC2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[C@@H]1C1=CC=C(O)C(O)=C13211.1Semi standard non polar33892256
3'-O-Methylcatechin,1TBDMS,isomer #4CO[C@H]1CC2=C(C=C(O)C=C2O[Si](C)(C)C(C)(C)C)O[C@@H]1C1=CC=C(O)C(O)=C13212.0Semi standard non polar33892256
3'-O-Methylcatechin,2TBDMS,isomer #1CO[C@H]1CC2=C(C=C(O)C=C2O[Si](C)(C)C(C)(C)C)O[C@@H]1C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13351.7Semi standard non polar33892256
3'-O-Methylcatechin,2TBDMS,isomer #2CO[C@H]1CC2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[C@@H]1C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13363.0Semi standard non polar33892256
3'-O-Methylcatechin,2TBDMS,isomer #3CO[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13382.7Semi standard non polar33892256
3'-O-Methylcatechin,2TBDMS,isomer #4CO[C@H]1CC2=C(C=C(O)C=C2O[Si](C)(C)C(C)(C)C)O[C@@H]1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C13352.9Semi standard non polar33892256
3'-O-Methylcatechin,2TBDMS,isomer #5CO[C@H]1CC2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[C@@H]1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C13360.3Semi standard non polar33892256
3'-O-Methylcatechin,2TBDMS,isomer #6CO[C@H]1CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)O[C@@H]1C1=CC=C(O)C(O)=C13312.4Semi standard non polar33892256
3'-O-Methylcatechin,3TBDMS,isomer #1CO[C@H]1CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)O[C@@H]1C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13492.9Semi standard non polar33892256
3'-O-Methylcatechin,3TBDMS,isomer #2CO[C@H]1CC2=C(C=C(O)C=C2O[Si](C)(C)C(C)(C)C)O[C@@H]1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13490.7Semi standard non polar33892256
3'-O-Methylcatechin,3TBDMS,isomer #3CO[C@H]1CC2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[C@@H]1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13479.6Semi standard non polar33892256
3'-O-Methylcatechin,3TBDMS,isomer #4CO[C@H]1CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)O[C@@H]1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C13499.4Semi standard non polar33892256
3'-O-Methylcatechin,4TBDMS,isomer #1CO[C@H]1CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)O[C@@H]1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13648.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3'-O-Methylcatechin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-O-Methylcatechin 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-Methylcatechin 10V, Positive-QTOFsplash10-0a4i-0209000000-d580f9b50e87df7ab0592021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-Methylcatechin 20V, Positive-QTOFsplash10-0a4i-0749000000-8243e1ef05b05306d4812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-Methylcatechin 40V, Positive-QTOFsplash10-022j-0790000000-b88499d61fc5d24a6e1c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-Methylcatechin 10V, Negative-QTOFsplash10-0udi-0009000000-04ccc09c7865adc860512021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-Methylcatechin 20V, Negative-QTOFsplash10-0fmr-0692000000-5433f783a89fb1b5effa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-O-Methylcatechin 40V, Negative-QTOFsplash10-00g0-2930000000-98942567bbe26ccc87402021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 770 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021479
KNApSAcK IDC00055676
Chemspider ID8555738
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10380295
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.. .
  2. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]