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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:39:28 UTC
Update Date2022-03-07 02:56:08 UTC
HMDB IDHMDB0039264
Secondary Accession Numbers
  • HMDB39264
Metabolite Identification
Common NameHeterophylliin A
DescriptionHeterophylliin A belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Heterophylliin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, heterophylliin a has been detected, but not quantified in, nuts. This could make heterophylliin a a potential biomarker for the consumption of these foods.
Structure
Data?1563863343
Synonyms
ValueSource
1,3-Di-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-a-D-glucopyranoseHMDB
3,4,5,12,21,22,23-Heptahydroxy-8,18-dioxo-13-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoic acidGenerator
Chemical FormulaC34H26O22
Average Molecular Weight786.557
Monoisotopic Molecular Weight786.091572516
IUPAC Name3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-11-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2,4,6,20,22-hexaen-13-yl 3,4,5-trihydroxybenzoate
Traditional Name3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-11-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2,4,6,20,22-hexaen-13-yl 3,4,5-trihydroxybenzoate
CAS Registry Number87687-52-3
SMILES
OC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)OC2C1OC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(48)55-29-27(47)34(56-31(49)9-3-14(37)22(42)15(38)4-9)53-18-7-52-32(50)10-5-16(39)23(43)25(45)19(10)20-11(33(51)54-28(18)29)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-47H,7H2
InChI KeyNLDMNSXOCDLTTB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative ParentsNot Available
SubstituentsNot Available
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 Solubility1.87 g/LALOGPS
logP2.67ALOGPS
logP2.68ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.34ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area377.42 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity178.06 m³·mol⁻¹ChemAxon
Polarizability69.51 ųChemAxon
Number of Rings6ChemAxon
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]+259.80630932474
DeepCCS[M-H]-258.01630932474
DeepCCS[M-2H]-292.04930932474
DeepCCS[M+Na]+265.98530932474
AllCCS[M+H]+253.632859911
AllCCS[M+H-H2O]+253.432859911
AllCCS[M+NH4]+253.832859911
AllCCS[M+Na]+253.932859911
AllCCS[M-H]-253.932859911
AllCCS[M+Na-2H]-256.632859911
AllCCS[M+HCOO]-259.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Heterophylliin AOC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)OC2C1OC(=O)C1=CC(O)=C(O)C(O)=C18970.3Standard polar33892256
Heterophylliin AOC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)OC2C1OC(=O)C1=CC(O)=C(O)C(O)=C16020.0Standard non polar33892256
Heterophylliin AOC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)OC2C1OC(=O)C1=CC(O)=C(O)C(O)=C17326.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0903074000-4f711d18e968c3f1e6302017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 10V, Positive-QTOFsplash10-0g4i-0900001300-052fea7a18e0053f20182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 20V, Positive-QTOFsplash10-0udi-0900000100-d733329fa7c3c5f4a29a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 40V, Positive-QTOFsplash10-0ufr-0900100100-391c88a7f1cff5ff30e42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 10V, Negative-QTOFsplash10-014r-0900001400-c865c1f847b730d795282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 20V, Negative-QTOFsplash10-014i-0921001100-8bf8e9d4f7fd396de3ed2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 40V, Negative-QTOFsplash10-014i-0903000000-8c2b0515add3f7f0a8c12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 10V, Negative-QTOFsplash10-000i-0300001900-f192731bc54b72fc95782021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 20V, Negative-QTOFsplash10-0gdi-0900003700-f71706ba0cfc0ccf0c3e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 40V, Negative-QTOFsplash10-00or-3900001200-5157baa34313794cb3782021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 10V, Positive-QTOFsplash10-014r-0900007200-0ad5c93e540729ce10c72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 20V, Positive-QTOFsplash10-0udr-1900104300-03ba33a25b96eded9ad72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heterophylliin A 40V, Positive-QTOFsplash10-0ufr-4902001400-c593c0fe1cf784e61f742021-09-25Wishart 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 IDFDB018805
KNApSAcK IDNot Available
Chemspider ID413780
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound471120
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.. .