Procyanidin C1 (CHEM031715)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:51:59 UTC
Update Date2016-11-09 01:19:19 UTC
Accession NumberCHEM031715
Identification
Common NameProcyanidin C1
ClassSmall Molecule
DescriptionA proanthocyanidin consisting of three (-)-epicatechin units joined by two successive (4beta->8)-linkages.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
[Epicatechin(4b->8)]2-epicatechinChEBI
[Epicatechin-(4beta->8)]2-epicatechinChEBI
Cinnamtannin a1ChEBI
EC-(4b,8)-ec-(4b,8)-ecChEBI
Epicatechin-(4beta->8)-epicatechin-(4beta->8)-epicatechinChEBI
Proanthocyanidin C1ChEBI
Procyanidin trimer C1ChEBI
Procyanidol C1ChEBI
[Epicatechin-(4b->8)]2-epicatechinGenerator
[Epicatechin-(4β->8)]2-epicatechinGenerator
Epicatechin-(4b->8)-epicatechin-(4b->8)-epicatechinGenerator
Epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechinGenerator
Chemical FormulaC45H38O18
Average Molecular Mass866.781 g/mol
Monoisotopic Mass866.206 g/mol
CAS Registry Number37064-30-5
IUPAC Name(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Nameproanthocyanidin C1
SMILES[H][C@]1([C@@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C2O[C@@H]([C@H](O)[C@@]([H])(C3=C(O)C=C(O)C4=C3O[C@@H]([C@H](O)C4)C3=CC(O)=C(O)C=C3)C2=C(O)C=C1O)C1=CC(O)=C(O)C=C1
InChI IdentifierInChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1
InChI KeyMOJZMWJRUKIQGL-XILRTYJMSA-N
Chemical Taxonomy
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
  • C-type proanthocyanidin
  • B-type proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Catechin
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavan
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP3.38ALOGPS
logP4.44ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.64ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area331.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity219.02 m³·mol⁻¹ChemAxon
Polarizability86.22 ųChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-016r-0340210090-7a35b5c8f1ccbf9ce4feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0100005690-161c67165e6b61ef57bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0100095720-02cbe7a0c9e7f5b22731Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-005a-0000091310-a37ac8e1536b30e63a1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000290-d007b6b11a94570a4ea1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0940310530-208f53a241f13af95f6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-0970202200-0b6a6c3437423c0f510fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-1908e9268dd08c7b8ec0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap0-0000000590-e0e939b2b90e92e9b2eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n1-0250010790-9209726cb0057ab3be6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0000000690-607bdbb728e2f09d08f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0100020590-0d606c193a998f7c0b1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0109-0910000580-1c47f69a0c96e4c8ee37Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0038370
FooDB IDFDB017710
Phenol Explorer ID157
KNApSAcK IDC00009098
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkProcyanidin_C1
Chemspider ID148540
ChEBI ID75643
PubChem Compound ID169853
Kegg Compound IDC17624
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18594151
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22000800
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22071171
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22796647
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23057780
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23222867
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23261363
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23459328
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23770004
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23870988
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24141365
12. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.