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Showing Compound Valoneic acid dilactone (FDB000230)

Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2019-11-26 02:54:34 UTC
Primary IDFDB000230
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameValoneic acid dilactone
DescriptionValoneic acid dilactone 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. Valoneic acid dilactone is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Valoneic acid dilactone can be found in cloves, common walnut, and japanese walnut, which makes valoneic acid dilactone a potential biomarker for the consumption of these food products. Valoneic acid dilactone is a hydrolysable tannin that can be isolated from the heartwood of Shorea laeviforia and in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur) .
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Valoneate dilactoneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.61ALOGPS
logP2.87ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area220.51 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity108.07 m³·mol⁻¹ChemAxon
Polarizability40.96 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H10O13
IUPAC name3,4,5-trihydroxy-2-({7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)benzoic acid
InChI IdentifierInChI=1S/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29)
InChI KeyBPAOAXAAABIQKR-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=C(OC2=C(O)C3=C4C(=C2)C(=O)OC2=C(O)C(O)=CC(C(=O)O3)=C42)C(O)=C(O)C(O)=C1
Average Molecular Weight470.298
Monoisotopic Molecular Weight470.012140382
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
  • Ellagic_acid
  • 7,8-dihydroxycoumarin
  • Gallic acid or derivatives
  • Gallic acid
  • Isocoumarin
  • Diaryl ether
  • Coumarin
  • Hydroxybenzoic acid
  • Benzopyran
  • 1-benzopyran
  • 2-benzopyran
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoic acid
  • Pyrogallol derivative
  • Phenol ether
  • Phenoxy compound
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Ether
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
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, Positivesplash10-00di-0000900000-2dc2a7bfa3ecc84f37e92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi0-0111900000-a6b9306781b8438fbc922016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0892100000-23a1f27c06a9e83c49372016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-0002900000-661e28445bb11125a1492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0215900000-82724a0258a9f186ac072016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-1891000000-e1722561d147420a1ecb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-0244494bf7a8d7e10c922021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0004900000-e8a787c0beca88e64c0e2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-0049400000-9e41873b0293ab8360f92021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-b2e7d8f9b0444bf16d262021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gbc-0104900000-8f0cd8a81d282388855b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-022d-2109300000-2e3bc0c8416a9e5a48db2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID440
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDVALONEIC ACID BISLACTONE
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Godevac D, Tesevic V, Vajs V, Milosavljevic S, Stankovic M: Antioxidant properties of raspberry seed extracts on micronucleus distribution in peripheral blood lymphocytes. Food Chem Toxicol. 2009 Nov;47(11):2853-9. Epub 2009 Sep 11. Pubmed [Structure]
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).