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Showing Compound Proanthocyanidin A2 (FDB016778)

Record Information
Version1.0
Creation date2010-04-08 22:12:38 UTC
Update date2019-11-26 03:13:46 UTC
Primary IDFDB016778
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProanthocyanidin A2
DescriptionProanthocyanidin A2 belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Proanthocyanidin A2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Proanthocyanidin A2 has been detected, but not quantified in, several different foods, such as herbs and spices, avocado, lingonberries, ceylon cinnamons, and apples. This could make proanthocyanidin A2 a potential biomarker for the consumption of these foods.
CAS Number41743-41-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.52ALOGPS
logP4.1ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.73ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area209.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity149.24 m³·mol⁻¹ChemAxon
Polarizability58.11 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC31H26O12
IUPAC name(1R,5R,6R,13S,21R)-13-(3,4-dihydroxy-5-methylphenyl)-5-(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol
InChI IdentifierInChI=1S/C31H26O12/c1-11-4-13(6-20(37)27(11)39)31-30(40)26(24-19(36)7-14(32)8-22(24)42-31)25-23(43-31)10-17(34)15-9-21(38)28(41-29(15)25)12-2-3-16(33)18(35)5-12/h2-8,10,21,26,28,30,32-40H,9H2,1H3/t21-,26-,28-,30-,31+/m1/s1
InChI KeyDWMJRBXZWVVPDB-UYVQOXPASA-N
Isomeric SMILESCC1=C(O)C(O)=CC(=C1)[C@@]12OC3=CC(O)=CC(O)=C3[C@@H]([C@H]1O)C1=C3O[C@@H]([C@H](O)CC3=C(O)C=C1O2)C1=CC=C(O)C(O)=C1
Average Molecular Weight590.5309
Monoisotopic Molecular Weight590.142426296
Classification
Description Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative Parents
Substituents
  • A-type proanthocyanidin
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Catechin
  • Pyranoflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • M-cresol
  • O-cresol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Ketal
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Toluene
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Acetal
  • Polyol
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0900580000-b35a41d6dd7d0f94b9c62016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0900830000-605c12946bf657edebea2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2900010000-662eef0e7f9ffc57f4bd2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0110290000-6e36ea0cc5dfe4653f5e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fe0-0900450000-e3f4fbc0903e73bb4d142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-0910000000-b64582e6c380a5e9a1172016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10237
Pubchem Compound ID124025
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID176
DrugBank IDNot Available
HMDB IDHMDB37655
CRC / DFC (Dictionary of Food Compounds) IDKTF42-T:KTF43-U
EAFUS IDNot Available
Dr. Duke IDPROANTHOCYANIDIN-A-2|PROCYANIDIN-A-2
BIGG IDNot Available
KNApSAcK IDC00002934
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).