Record Information
Version1.0
Creation date2010-04-08 22:13:15 UTC
Update date2019-11-26 03:15:04 UTC
Primary IDFDB017699
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLeucocyanidin
DescriptionLeucocyanidin, also known as 3,3',4,4',5,7-flavanhexol or resivit, is a member of the class of compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Thus, leucocyanidin is considered to be a flavonoid lipid molecule. Leucocyanidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Leucocyanidin can be found in a number of food items such as climbing bean, black mulberry, corn salad, and caraway, which makes leucocyanidin a potential biomarker for the consumption of these food products. Leucocyanidin is a colorless chemical compound that is a member of the class of natural products known as leucoanthocyanidins .
CAS Number480-17-1
Structure
Thumb
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrolChEBI
3,3',4,4',5,7-FlavanhexolChEBI
3,4-CyanidiolChEBI
LeucoanthocyanidolChEBI
LeucocianidolChEBI
LeucocyanidolChEBI
LeukocyanidineChEBI
ProcyanidolChEBI
ResivitChEBI
3,3',4,4',5,7-FlavanhexanolMeSH
3,3',4,4',5,7-HexahydroflavaneMeSH
5,7,3,4-Tetrahydroxyflavan-3',4'-diolMeSH
Venen tabsMeSH
FlavanhexanolMeSH
LeucodyanidolMeSH
2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-benzopyran-3,4,5,7-tetrol, 9CIdb_source
Leucanthocyanidoldb_source
Leucocianidol, INNdb_source
Leucocyanidindb_source
Pygnofortondb_source
Pyknogenoldb_source
Predicted Properties
PropertyValueSource
Water Solubility2.22 g/LALOGPS
logP0.44ALOGPS
logP0.88ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)8.95ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area130.61 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.21 m³·mol⁻¹ChemAxon
Polarizability28.84 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H14O7
IUPAC name2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
InChI IdentifierInChI=1S/C15H14O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,13-21H
InChI KeySBZWTSHAFILOTE-UHFFFAOYSA-N
Isomeric SMILESOC1C(O)C2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C=C1
Average Molecular Weight306.2675
Monoisotopic Molecular Weight306.073952802
Classification
Description Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • Leucoanthocyanidin-skeleton
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • 4-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.83%; H 4.61%; O 36.57%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 285 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004r-0950000000-538e24b231bc36c09f482017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0900000000-797dae0ccbdefbfd105b2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004r-0591000000-e96e5118c1fd0f849dad2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0ufr-0696101000-edfdbd9489a088bbb6002017-08-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0229000000-f16f1b0ba3ccec0c57f62015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0921000000-7b8492b35e171f503e182015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059i-2900000000-5d19792f638eed4895732015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0309000000-a9fdfdae71bf3feadbdd2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0933000000-7b7b8949cd99285d0f5f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3910000000-2217a1d0c4ee0b9286482015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0239000000-88a49cd6374b617d22aa2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-0911000000-06fdf563a5ddcdb02d8d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1910000000-e895c788a190d251d0662021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-408fca4c89a0c93ccd332021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-0941000000-4f41d8f8c299bca544b62021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zmi-0920000000-c9e0db584f9840cf1fbd2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDKZF25-G:KZF25-G
EAFUS IDNot Available
Dr. Duke IDLEUCOCYANIDIN
BIGG IDNot Available
KNApSAcK IDC00007235
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
capillariprotectiveDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— 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.