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Identification
YMDB IDYMDB01726
NameLeucocyanidin
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description(2R,3S,4S)-leucocyanidin, also known as 3,3',4,4',5,7-flavanhexol or 3,4-cyanidiol, 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. Thus, (2R,3S,4S)-leucocyanidin is considered to be a flavonoid lipid molecule (2R,3S,4S)-leucocyanidin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (2R,3S,4S)-leucocyanidin may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • (2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,4,5,7-tetrol
  • (2R,3S,4S)-2-(3,4-dihydroxyphenyl)chromane-3,4,5,7-tetrol
  • 2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
  • 2,3-trans-3,4-cis-Leucocyanidin
  • 3,3',4,4',5,7-Flavanhexol
  • 3,4-Cyanidiol
  • Leucoanthocyanidol
  • Leucocianidol
  • Leucocyanidin
  • Leucocyanidol
  • Leukocyanidine
  • Procyanidol
  • Resivit
  • Flavan
CAS number480-17-1
WeightAverage: 306.2675
Monoisotopic: 306.073952802
InChI KeySBZWTSHAFILOTE-SOUVJXGZSA-N
InChIInChI=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/t13-,14-,15+/m0/s1
IUPAC Name(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
Traditional IUPAC Nameprocyanidol
Chemical FormulaC15H14O7
SMILESO[C@H]1[C@@H](O)C2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1
Chemical Taxonomy
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
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Polarizability29.36 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15758
HMDB IDNot Available
Pubchem Compound ID440833
Kegg IDC05906
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available