Record Information
Version1.0
Creation date2010-04-08 22:14:02 UTC
Update date2019-11-26 03:16:54 UTC
Primary IDFDB018932
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVescalagincarboxylic acid
DescriptionVescalagincarboxylic acid is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins 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) 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. Vescalagincarboxylic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Vescalagincarboxylic acid can be found in guava, which makes vescalagincarboxylic acid a potential biomarker for the consumption of this food product.
CAS Number118964-19-5
Structure
Thumb
Synonyms
SynonymSource
VescalagincarboxylateGenerator
Vescalagin carboxylic acidbiospider
Vescalagincarboxylic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility7.01 g/LALOGPS
logP3.07ALOGPS
logP2.32ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.92ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area472.25 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity217.56 m³·mol⁻¹ChemAxon
Polarizability84.13 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC42H26O27
IUPAC name7,8,9,12,13,14,25,26,27,30,31,32,35,36,37-pentadecahydroxy-4,17,22,40,44-pentaoxo-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-46-carboxylic acid
InChI IdentifierInChI=1S/C42H26O27/c43-8-1-5-12(25(49)22(8)46)13-6(2-9(44)23(47)26(13)50)40(62)67-34-11(4-65-38(5)60)66-39(61)7-3-10(45)24(48)27(51)14(7)15-19-16(29(53)32(56)28(15)52)17-20-18(31(55)33(57)30(17)54)21(37(58)59)35(68-41(20)63)36(34)69-42(19)64/h1-3,11,21,34-36,43-57H,4H2,(H,58,59)
InChI KeyZTOKIAYQNMCRRX-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1C2OC(=O)C3=C(C(O)=C(O)C(O)=C13)C1=C3C(=C(O)C(O)=C1O)C1=C(C=C(O)C(O)=C1O)C(=O)OC1COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)OC1C2OC3=O
Average Molecular Weight962.6396
Monoisotopic Molecular Weight962.066145626
Classification
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 Parents
Substituents
  • Hydrolyzable tannin
  • Hexacarboxylic acid or derivatives
  • Gallic acid or derivatives
  • Benzopyran
  • Isochromane
  • 2-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.40%; H 2.72%; O 44.87%DFC
Melting PointMp 180° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D -59.3 (c, 0.60 in MeOH aq.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0005002009-fa42b7650ab862013b37Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0022000009-beee61db7085d9a15825Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-0094512400-132c7a64c5177c7ef4caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0000000019-f7b6ca7331441d7456ddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-0000000159-7a2bb36c466334a7abf9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdp-1880021039-d9c7e0495ca6fe6dd0baSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID16131089
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDLNJ53-M:LNH47-D
EAFUS IDNot Available
Dr. Duke IDVESCALAGIN-CARBOXYLIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).