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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:39:43 UTC
Update Date2022-03-07 02:55:44 UTC
HMDB IDHMDB0038360
Secondary Accession Numbers
  • HMDB38360
Metabolite Identification
Common NameTheasinensin A
DescriptionTheasinensin A belongs to the class of organic compounds known as complex tannins. These are tannins made of a catechin bound to a gallotannin or elagitannin. Theasinensin A is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea and black tea. This could make theasinensin a a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Theasinensin A.
Structure
Data?1563863184
SynonymsNot Available
Chemical FormulaC44H34O22
Average Molecular Weight914.734
Monoisotopic Molecular Weight914.154172735
IUPAC Name(2R,3R)-2-{6'-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-2-yl]-2',3',4,4',5,6-hexahydroxy-[1,1'-biphenyl]-2-yl}-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(2R,3R)-2-{6'-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-2-yl]-2',3',4,4',5,6-hexahydroxy-[1,1'-biphenyl]-2-yl}-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry Number89064-31-3
SMILES
OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2C2=C(C=C(O)C(O)=C2O)[C@H]2OC3=C(C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)=CC(O)=C3)C(O)=C1
InChI Identifier
InChI=1S/C44H34O22/c45-15-5-21(47)17-11-31(65-43(61)13-1-23(49)35(55)24(50)2-13)41(63-29(17)7-15)19-9-27(53)37(57)39(59)33(19)34-20(10-28(54)38(58)40(34)60)42-32(12-18-22(48)6-16(46)8-30(18)64-42)66-44(62)14-3-25(51)36(56)26(52)4-14/h1-10,31-32,41-42,45-60H,11-12H2/t31-,32-,41-,42-/m1/s1
InChI KeyYUULFXAQUWEYNP-GXAWFILRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as complex tannins. These are tannins made of a catechin bound to a gallotannin or elagitannin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassComplex tannins
Direct ParentComplex tannins
Alternative Parents
Substituents
  • Complex tannin
  • Catechin gallate
  • Epigallocatechin
  • Catechin
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Flavan
  • Biphenol
  • Galloyl ester
  • Gallic acid or derivatives
  • Biphenyl
  • P-hydroxybenzoic acid ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid alkyl ester
  • 1-benzopyran
  • Benzopyran
  • Benzoate ester
  • Chromane
  • Benzenetriol
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Ether
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP3.48ALOGPS
logP5.83ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.76ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area394.74 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity222.57 m³·mol⁻¹ChemAxon
Polarizability83.43 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]+279.83930932474
DeepCCS[M-H]-278.11530932474
DeepCCS[M-2H]-312.14830932474
DeepCCS[M+Na]+286.16830932474
AllCCS[M+H]+283.632859911
AllCCS[M+H-H2O]+283.732859911
AllCCS[M+NH4]+283.532859911
AllCCS[M+Na]+283.432859911
AllCCS[M-H]-287.732859911
AllCCS[M+Na-2H]-292.432859911
AllCCS[M+HCOO]-297.632859911

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, 2022.3.98 minutes32390414
Predicted by Siyang on May 30, 202215.1409 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.89 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid101.9 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1787.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid120.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid107.4 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid79.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid194.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid1088.9 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 Acid574.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)1182.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid896.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid449.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1924.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid308.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid438.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate576.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA582.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water784.5 seconds40023050

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Theasinensin A , positive-QTOFsplash10-000i-0930300000-09eb58349fe15793d0352017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 10V, Positive-QTOFsplash10-00kr-0900000203-58c8d064e6520a64fef92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 20V, Positive-QTOFsplash10-0fe0-0900000100-66f241797c061dfe43812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 40V, Positive-QTOFsplash10-0fe0-1900000010-6d44b0c7bb14b5794b9c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 10V, Negative-QTOFsplash10-03di-0300000119-35c4d97fd0c28d371d3b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 20V, Negative-QTOFsplash10-07fr-0901211522-74eba17741422040ad242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 40V, Negative-QTOFsplash10-00or-0900000000-1ea7e5ed24733bccf7192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 10V, Negative-QTOFsplash10-03di-0000000903-f57add13a8419943ef712021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 20V, Negative-QTOFsplash10-03g0-0900000253-9bb7bc010bc2b859b9552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 40V, Negative-QTOFsplash10-004i-0900000170-0819238d60a5ffea99e72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 10V, Positive-QTOFsplash10-00kb-0100000926-34ffa23f617263dbb9c92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 20V, Positive-QTOFsplash10-0gbj-0900000564-a0651e4364ae3c855c3a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theasinensin A 40V, Positive-QTOFsplash10-102a-1900020251-41265bea395eaa100ec52021-09-24Wishart 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 IDFDB018261
KNApSAcK IDC00001010
Chemspider ID390965
KEGG Compound IDC09972
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTheasinensin A
METLIN IDNot Available
PubChem Compound5152597
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.. .