Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:46:11 UTC
Update Date2022-03-07 02:53:09 UTC
HMDB IDHMDB0031888
Secondary Accession Numbers
  • HMDB31888
Metabolite Identification
Common NameTheacitrin A
DescriptionTheacitrin A belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. Based on a literature review very few articles have been published on Theacitrin A.
Structure
Data?1563862186
Synonyms
ValueSource
2-[5,7,8a-Trihydroxy-1,6,8-trioxo-3-(3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)-1H,3ah,3BH,6H,8H,8ah-cyclopenta[a]inden-3b-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidHMDB
Theacitrin aMeSH
Chemical FormulaC37H28O18
Average Molecular Weight760.6074
Monoisotopic Molecular Weight760.127564092
IUPAC Name2-[5,7,8a-trihydroxy-1,6,8-trioxo-3-(3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)-1H,3aH,3bH,6H,8H,8aH-cyclopenta[a]inden-3b-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name2-[5,7,8a-trihydroxy-1,6,8-trioxo-3-(3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)-3aH-cyclopenta[a]inden-3b-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry Number201998-49-4
SMILES
OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(=O)C2(O)C1C1(C=C(O)C(=O)C(O)=C1C2=O)C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C37H28O18/c38-12-3-17(40)14-7-21(44)31(53-23(14)5-12)16-9-26(46)37(52)32(16)36(10-22(45)29(48)30(49)27(36)33(37)50)34-25(8-15-18(41)4-13(39)6-24(15)54-34)55-35(51)11-1-19(42)28(47)20(43)2-11/h1-6,9-10,21,25,31-32,34,38-45,47,49,52H,7-8H2
InChI KeyWCQMIZTZMRUYPY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentGalloyl esters
Alternative Parents
Substituents
  • Galloyl ester
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • 1-benzopyran
  • Benzoate ester
  • Chromane
  • Benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoyl
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Cyclic alcohol
  • Tertiary alcohol
  • Vinylogous acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Cyclic ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Enol
  • Ether
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • 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 Solubility0.0038 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP2.32ALOGPS
logP1.72ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)5.94ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area318.5 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity184.12 m³·mol⁻¹ChemAxon
Polarizability70.23 ųChemAxon
Number of Rings8ChemAxon
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+H]+256.34530932474
DeepCCS[M-H]-254.62530932474
DeepCCS[M-2H]-288.6630932474
DeepCCS[M+Na]+262.50230932474
AllCCS[M+H]+258.332859911
AllCCS[M+H-H2O]+257.832859911
AllCCS[M+NH4]+258.832859911
AllCCS[M+Na]+258.932859911
AllCCS[M-H]-261.932859911
AllCCS[M+Na-2H]-265.432859911
AllCCS[M+HCOO]-269.432859911

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, 2022.4.65 minutes32390414
Predicted by Siyang on May 30, 202212.6162 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.69 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid108.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2352.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid157.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid106.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid124.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid101.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid730.3 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 Acid463.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)793.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid789.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid451.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1879.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid311.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid370.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate423.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA264.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water523.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Theacitrin AOC1CC2=C(O)C=C(O)C=C2OC1C1=CC(=O)C2(O)C1C1(C=C(O)C(=O)C(O)=C1C2=O)C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C19343.3Standard polar33892256
Theacitrin AOC1CC2=C(O)C=C(O)C=C2OC1C1=CC(=O)C2(O)C1C1(C=C(O)C(=O)C(O)=C1C2=O)C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C15597.5Standard non polar33892256
Theacitrin AOC1CC2=C(O)C=C(O)C=C2OC1C1=CC(=O)C2(O)C1C1(C=C(O)C(=O)C(O)=C1C2=O)C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C17213.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TBDMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TBDMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TBDMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TBDMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TBDMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Theacitrin A GC-MS (TBDMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 10V, Positive-QTOFsplash10-01ox-0700131900-3619c63195fb731320902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 20V, Positive-QTOFsplash10-0f79-0900110100-743b08e2e8d053c699a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 40V, Positive-QTOFsplash10-0fk9-1900210100-f175e7f7d8058b7cf2e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 10V, Negative-QTOFsplash10-0a4i-0400001900-24e9d3f71c2d280e73802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 20V, Negative-QTOFsplash10-06g0-0900215400-dc8c8d56f686287432cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 40V, Negative-QTOFsplash10-00or-0900000000-f23d540c1edf612f99e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 10V, Positive-QTOFsplash10-03dl-0000010900-2e1458040256cbf2422e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 20V, Positive-QTOFsplash10-03du-0200021900-a778bf269162f11b5f362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 40V, Positive-QTOFsplash10-000l-1800419500-e38ba7924cd08e6357162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 10V, Negative-QTOFsplash10-0a4i-0100000900-64722b5f10488ade89522021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 20V, Negative-QTOFsplash10-0a4u-0600131900-2df8b88ab36c10b97faa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theacitrin A 40V, Negative-QTOFsplash10-007c-2900107400-47897143e918ef07c29e2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB008573
KNApSAcK IDC00058003
Chemspider ID35013396
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751199
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1828411
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.. .