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Showing Compound Guavin A (FDB018811)

Record Information
Version1.0
Creation date2010-04-08 22:13:57 UTC
Update date2019-11-26 03:16:43 UTC
Primary IDFDB018811
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGuavin A
DescriptionGuavin 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. Guavin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Guavin A has been detected, but not quantified in, fruits and guava. This could make guavin a a potential biomarker for the consumption of these foods.
CAS Number105581-34-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility3.32 g/LALOGPS
logP2.98ALOGPS
logP3.34ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.4ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count27ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area551.4 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity281.88 m³·mol⁻¹ChemAxon
Polarizability110.07 ųChemAxon
Number of Rings12ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC56H40O32
IUPAC name(10R,11R)-10-[(4S,5S,14R,15S,19R)-19-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,3,4,8,9-pentahydroxy-2,12,17-trioxo-13,16,20-trioxapentacyclo[13.3.1.1^{4,7}.0^{5,18}.0^{6,11}]icosa-1(18),6,8,10-tetraen-14-yl]-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0^{2,7}]nonadeca-1(19),2,4,6,15,17-hexaen-11-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C56H40O32/c57-18-2-1-12(3-20(18)59)43-27(66)6-14-19(58)10-21(60)32(44(14)84-43)33-34-35-36-31-17(9-26(65)40(70)46(31)88-56(36,81)55(79,80)49(34)73)53(77)87-48(47(33)86-54(35)78)45-28(83-50(74)13-4-22(61)37(67)23(62)5-13)11-82-51(75)15-7-24(63)38(68)41(71)29(15)30-16(52(76)85-45)8-25(64)39(69)42(30)72/h1-5,7-10,27-28,33,36,43,45,47-48,57-72,79-81H,6,11H2/t27-,28+,33+,36-,43+,45+,47-,48-,56-/m0/s1
InChI KeyDOMGXWDOTMOBEH-IFNRHMFZSA-N
Isomeric SMILES[H][C@@]12C3=C4C=C(O)C(O)=C3O[C@]1(O)C(O)(O)C(=O)C1=C2C(=O)O[C@H]([C@@H](OC4=O)[C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(C=C(O)C(O)=C3O)C(=O)OC[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@]1([H])C1=C2O[C@@H]([C@@H](O)CC2=C(O)C=C1O)C1=CC(O)=C(O)C=C1
Average Molecular Weight1224.8976
Monoisotopic Molecular Weight1224.150269184
Classification
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
  • 8-prenylated flavan
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Pentacarboxylic acid or derivatives
  • Flavan
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Benzoate ester
  • Coumaran
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzenetriol
  • Catechol
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexenone
  • Phenol
  • Dihydropyranone
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Lactone
  • Ketone
  • Hemiacetal
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Carboxylic acid derivative
  • Carbonyl hydrate
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID73814546
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39269
CRC / DFC (Dictionary of Food Compounds) IDLMT11-P:LMT11-P
EAFUS IDNot Available
Dr. Duke IDGUAVIN-A
BIGG IDNot Available
KNApSAcK IDC00009364
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
GuavaExpected but not quantifiedNot AvailableDUKE, KNAPSACK
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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 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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.