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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 cinnamtannin A1 or procyanidol 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 is found, on average, in the highest concentration within a few different foods, such as chocolate, cocoa powder, and apples (Malus pumila) and in a lower concentration in broad beans (Vicia faba), chestnuts (Castanea), and pears (Pyrus communis). Procyanidin C1 has also been detected, but not quantified in, several different foods, such as yellow zucchinis (Cucurbita pepo var. cylindrica), lettuces (Lactuca sativa), pineapples (Ananas comosus), garden tomato (var.), and fruit juice. This could make procyanidin C1 a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Procyanidin C1.
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-3.6ALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-016r-0340210090-7a35b5c8f1ccbf9ce4fe2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0100005690-161c67165e6b61ef57bb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0100095720-02cbe7a0c9e7f5b227312016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-005a-0000091310-a37ac8e1536b30e63a1e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000290-d007b6b11a94570a4ea12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0940310530-208f53a241f13af95f6b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-0970202200-0b6a6c3437423c0f510f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-1908e9268dd08c7b8ec02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap0-0000000590-e0e939b2b90e92e9b2ee2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n1-0250010790-9209726cb0057ab3be6f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0000000690-607bdbb728e2f09d08f32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0100020590-0d606c193a998f7c0b1c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0109-0910000580-1c47f69a0c96e4c8ee372021-09-23View Spectrum
NMRNot Available
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
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.CHEBI
Lipoxygenase inhibitor35856 An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.CHEBI
Xanthine oxidase inhibitor35634 An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.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.