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Showing Compound Procyanidin C1 (FDB017710)

Record Information
Version1.0
Creation date2010-04-08 22:13:15 UTC
Update date2019-11-26 03:15:06 UTC
Primary IDFDB017710
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProcyanidin C1
DescriptionProcyanidin C1, also known as procyanidin C1 or procyanidin C1, 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''. Procyanidin C1 exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Procyanidin C1 is found , on average, in the highest concentration in a few different foods, such as chocolates, cocoa powders, and apples and in a lower concentration in pears, custard apples, and peach (var.). Procyanidin C1 has also been detected, but not quantified in, several different foods, such as apple ciders, loquats, pepper (c. annuum), green zucchinis, and common wheats. This could make procyanidin C1 a potential biomarker for the consumption of these foods.
CAS Number37064-30-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
[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
[Epicatechin(4b->8)]2epicatechindb_source
EC-(4b,8)-EC-(4b,8)-ECdb_source
Procyanidin C1db_source
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP3.38ALOGPS
logP4.44ChemAxon
logS-3.5ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC45H38O18
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
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
Isomeric 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
Average Molecular Weight866.781
Monoisotopic Molecular Weight866.205814384
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
  • 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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.36%; H 4.42%; O 33.23%DFC
Melting Point140.0-142.0 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +102 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-016r-0340210090-7a35b5c8f1ccbf9ce4feJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0100005690-161c67165e6b61ef57bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0100095720-02cbe7a0c9e7f5b22731JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-005a-0000091310-a37ac8e1536b30e63a1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000290-d007b6b11a94570a4ea1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0940310530-208f53a241f13af95f6bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-0970202200-0b6a6c3437423c0f510fJSpectraViewer
ChemSpider ID148540
ChEMBL IDCHEMBL290632
KEGG Compound IDC17624
Pubchem Compound ID169853
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID157
DrugBank IDNot Available
HMDB IDHMDB38370
CRC / DFC (Dictionary of Food Compounds) IDKZF49-Q:KZF50-K
EAFUS IDNot Available
Dr. Duke IDPROANTHOCYANIDIN-C1|PROCYANIDIN-C-1
BIGG IDNot Available
KNApSAcK IDC00009098
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDProanthocyanidin_C1
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
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.CHEBI
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.CHEBI
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).CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— 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.