Record Information
Version1.0
Creation date2010-04-08 22:07:30 UTC
Update date2019-11-26 03:01:34 UTC
Primary IDFDB007228
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRugosin A
DescriptionRugosin a 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. Rugosin a is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Rugosin a can be found in cloves, which makes rugosin a a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP3.76ALOGPS
logP4.82ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area531.17 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity251.28 m³·mol⁻¹ChemAxon
Polarizability96.88 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC48H34O31
IUPAC name3,4,5-trihydroxy-2-{[3,4,5,22,23-pentahydroxy-8,18-dioxo-11,12,13-tris(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2(7),3,5,20,22-hexaen-21-yl]oxy}benzoic acid
InChI IdentifierInChI=1S/C48H34O31/c49-17-1-11(2-18(50)29(17)57)43(68)77-40-39-26(75-48(79-45(70)13-5-21(53)31(59)22(54)6-13)41(40)78-44(69)12-3-19(51)30(58)20(52)4-12)10-73-46(71)15-9-25(74-38-16(42(66)67)8-24(56)33(61)37(38)65)34(62)36(64)28(15)27-14(47(72)76-39)7-23(55)32(60)35(27)63/h1-9,26,39-41,48-65H,10H2,(H,66,67)
InChI KeyOMQLRKHSGHBOQC-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=C(OC2=CC3=C(C(O)=C2O)C2=C(C=C(O)C(O)=C2O)C(=O)OC2C(COC3=O)OC(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C2OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)=C(O)C(O)=C1
Average Molecular Weight1106.765
Monoisotopic Molecular Weight1106.10840437
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
  • Galloyl ester
  • Gallic acid
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • Diaryl ether
  • Hydroxybenzoic acid
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzenetriol
  • Pyrogallol derivative
  • Benzoic acid
  • Benzoyl
  • Phenoxy compound
  • Phenol ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Carboxylic acid ester
  • Lactone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Ether
  • Carboxylic acid
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen 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, Positivesplash10-0kg9-3900201118-ffb68ffbd416d3900a86Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uki-3900220115-206feae9405373f90291Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-0900600001-1145a6bf5b9d2ed7140dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ly9-5900000017-a84d2c8bcb241626fe93Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2902010223-1699b1796c0be8b96b1bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-0900000000-e09f037fe79fd1c03e83Spectrum
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 IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFL69-V:BFL69-V
EAFUS IDNot Available
Dr. Duke IDRUGOSIN-A
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
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).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).