Record Information
Version1.0
Creation date2010-04-08 22:12:38 UTC
Update date2018-05-29 01:28:03 UTC
Primary IDFDB016778
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProanthocyanidin A2
DescriptionIsolated from cassia bark (Cinnamomum aromaticum). Proanthocyanidin A2 is found in many foods, some of which are herbs and spices, cinnamon, avocado, and lingonberry.
CAS Number41743-41-3
Structure
Thumb
Synonyms
SynonymSource
(+)-Proanthocyanidin a2HMDB
EC-(4b,8)(2b,7)-ecHMDB
Epicatechin-(2b->7,4b->8)-epicatechinHMDB
Epicatechin-(2beta->7,4beta->8)-epicatechinHMDB
Proanthocyanidin a-2HMDB
Procyanidin a2HMDB
Procyanidin dimer a2HMDB
ProcyanidoepicatechinHMDB
Procyanidol a2HMDB
(+)-Proanthocyanidin A2biospider
EC-(4b,8)(2b,7)-ECdb_source
Proanthocyanidin A-2biospider
Proanthocyanidin A2db_source
Procyanidin A2db_source
Procyanidin dimer A2db_source
Procyanidol A2biospider
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
DescriptionThis compound belongs to the class of organic compounds known as proanthocyanidins. These are molecules containing an oligomeric moiety of C4-C8 and/or C4-C6 and/or C2-C7 oligo/polymers of flavan-3-ols.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassProanthocyanidins
Direct ParentProanthocyanidins
Alternative Parents
Substituents
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Catechin
  • Pyranoflavonoid
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Resorcinol
  • O-cresol
  • M-cresol
  • 1,2-diphenol
  • Toluene
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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 62.50%; H 4.20%; O 33.30%DFC
Melting PointMp 300°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +64 (Me2CO)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0900580000-b35a41d6dd7d0f94b9c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0900830000-605c12946bf657edebeaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2900010000-662eef0e7f9ffc57f4bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0110290000-6e36ea0cc5dfe4653f5eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fe0-0900450000-e3f4fbc0903e73bb4d14JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-0910000000-b64582e6c380a5e9a117JSpectraViewer
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti capillary-fragilityDUKE
anti elastase23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
anti enzymaticDUKE
anti erythemic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti glucuronidase23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti peroxidantDUKE
anti proteolyticDUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
venotonicDUKE
vulnerary73336 A drug used in treating and healing of wounds.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— 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).