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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:41:03 UTC
Update Date2022-03-07 02:55:44 UTC
HMDB IDHMDB0038375
Secondary Accession Numbers
  • HMDB38375
Metabolite Identification
Common NameCatechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin
DescriptionCatechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin has been detected, but not quantified in, a few different foods, such as barleys (Hordeum vulgare), breakfast cereal, and cereals and cereal products. This could make catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin.
Structure
Data?1563863187
Synonyms
ValueSource
Catechin-(4a->8)-gallocatechin-(4a->8)-catechinGenerator
Catechin-(4α->8)-gallocatechin-(4α->8)-catechinGenerator
Catechin(4a->8)gallocatechin(4a->8)catechinHMDB
Chemical FormulaC45H38O19
Average Molecular Weight882.7718
Monoisotopic Molecular Weight882.200729034
IUPAC Name8-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name8-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
CAS Registry Number87421-89-4
SMILES
OC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C(C1C(O)C(OC3=C(C4C(O)C(OC5=CC(O)=CC(O)=C45)C4=CC(O)=C(O)C=C4)C(O)=CC(O)=C13)C1=CC(O)=C(O)C(O)=C1)=C(O)C=C2O
InChI Identifier
InChI=1S/C45H38O19/c46-17-9-24(52)32-31(10-17)62-42(15-2-4-20(48)23(51)6-15)39(60)36(32)34-26(54)13-27(55)35-37(40(61)43(64-45(34)35)16-7-28(56)38(59)29(57)8-16)33-25(53)12-21(49)18-11-30(58)41(63-44(18)33)14-1-3-19(47)22(50)5-14/h1-10,12-13,30,36-37,39-43,46-61H,11H2
InChI KeyIHBGHNWUFNXKJX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative Parents
Substituents
  • C-type proanthocyanidin
  • B-type proanthocyanidin
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Epigallocatechin
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Benzenetriol
  • Pyrogallol derivative
  • Catechol
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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 Solubility0.33 g/LALOGPS
logP3.22ALOGPS
logP4.13ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.53ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area351.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity221 m³·mol⁻¹ChemAxon
Polarizability84.42 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-314.56630932474
DeepCCS[M+Na]+288.73630932474
AllCCS[M+H]+285.232859911
AllCCS[M+H-H2O]+285.132859911
AllCCS[M+NH4]+285.232859911
AllCCS[M+Na]+285.232859911
AllCCS[M-H]-281.732859911
AllCCS[M+Na-2H]-286.532859911
AllCCS[M+HCOO]-291.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.65 minutes32390414
Predicted by Siyang on May 30, 202212.2184 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.16 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid241.9 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid960.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid114.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid109.4 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid109.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid106.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid622.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid409.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)1215.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid678.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid301.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1187.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid206.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid299.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate526.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA778.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water716.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechinOC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C(C1C(O)C(OC3=C(C4C(O)C(OC5=CC(O)=CC(O)=C45)C4=CC(O)=C(O)C=C4)C(O)=CC(O)=C13)C1=CC(O)=C(O)C(O)=C1)=C(O)C=C2O10303.6Standard polar33892256
Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechinOC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C(C1C(O)C(OC3=C(C4C(O)C(OC5=CC(O)=CC(O)=C45)C4=CC(O)=C(O)C=C4)C(O)=CC(O)=C13)C1=CC(O)=C(O)C(O)=C1)=C(O)C=C2O5886.7Standard non polar33892256
Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechinOC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C(C1C(O)C(OC3=C(C4C(O)C(OC5=CC(O)=CC(O)=C45)C4=CC(O)=C(O)C=C4)C(O)=CC(O)=C13)C1=CC(O)=C(O)C(O)=C1)=C(O)C=C2O9208.6Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 10V, Positive-QTOFsplash10-00lr-0100011890-b58f7271cbbefdb8247c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 20V, Positive-QTOFsplash10-052f-0200093720-1354d6aa604cac3aed102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 40V, Positive-QTOFsplash10-00pm-0100090310-fb7b2d2b09ba190d666b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 10V, Negative-QTOFsplash10-001i-0100010290-e8fc3c2ba0700742afb82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 20V, Negative-QTOFsplash10-0udr-0920120220-cce8a8f62a6698d6087f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 40V, Negative-QTOFsplash10-002r-0961200200-d88b7ca23bb62b5aba912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 10V, Negative-QTOFsplash10-001i-0000000090-62c2a3f34e0b5eb1e2862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 20V, Negative-QTOFsplash10-0c30-0000000490-500849c7e31c68e37c6e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 40V, Negative-QTOFsplash10-00bi-0790010470-b8469f2e3900a63128d32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 10V, Positive-QTOFsplash10-001i-0000000490-9886571bfa3e9d927d662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 20V, Positive-QTOFsplash10-06ur-0110020980-86d4b9820d74a91415332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Catechin-(4alpha->8)-gallocatechin-(4alpha->8)-catechin 40V, Positive-QTOFsplash10-00ai-0302110790-01246d69138ce23047022021-09-22Wishart 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 IDFDB017718
KNApSAcK IDC00009099
Chemspider ID35014559
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752348
PDB IDNot Available
ChEBI ID168710
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.. .