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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:10 UTC
Update Date2019-07-23 06:10:49 UTC
HMDB IDHMDB0032322
Secondary Accession Numbers
  • HMDB32322
Metabolite Identification
Common NameLeucopelargonidin
DescriptionLeucopelargonidin (CAS: 520-17-2) is a colourless chemical compound belonging to the family of leucoanthocyanidins. Leucoanthocyanidins are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions. Leucopelargonidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Leucopelargonidin can be found in a number of food items such as narrowleaf cattail, pepper (C. pubescens), macadamia nut (M. tetraphylla), and abiyuch, which makes leucopelargonidin a potential biomarker for the consumption of these food products (FooDB). Leucopelargonidin can also be found in Albizia lebbeck (East Indian walnut), in the fruit of Anacardium occidentale (cashew), in the fruit of Areca catechu (Areca nut), in the fruit of Hydnocarpus wightiana (Hindi Chaulmoogra), in the rhizome of Rumex hymenosepalus (Arizona dock), in Zea Mays (corn), and in Ziziphus jujuba (Chinese date) (Wikipedia).
Structure
Data?1563862249
Synonyms
ValueSource
(+)-LeucopelargonidinChEBI
3,4-cis-LeucopelargonidineHMDB
(2R,3S,4S)-LeucopelargonidinHMDB
3,4,4',5,7-FlavanpentolHMDB
GoratensidinCAS
LeucopelargonidinHMDB
LeucopelargonidineCAS
LeucopelargonidolCAS
Chemical FormulaC15H14O6
Average Molecular Weight290.2681
Monoisotopic Molecular Weight290.07903818
IUPAC Name(2R,3S,4S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
Traditional Namecis-3,4-leucopelargonidin
CAS Registry Number98919-66-5
SMILES
O[C@H]1[C@@H](O)C2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C15H14O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,13-20H/t13-,14-,15+/m0/s1
InChI KeyFSVMLWOLZHGCQX-SOUVJXGZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentLeucoanthocyanidins
Alternative Parents
Substituents
  • Leucoanthocyanidin-skeleton
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Resorcinol
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.84 g/LALOGPS
logP0.62ALOGPS
logP1.18ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.08ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.23 m³·mol⁻¹ChemAxon
Polarizability28.69 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0970000000-3e60660dfaca3137796cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-000i-2100069000-3ce0116528533bd0d171JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-8b627d02db62b9f1f86cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abc-0950000000-2b74806e03f640f7e796JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g0-4900000000-59f4d5454c4db4612e0cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-6d8231aab24727e61b96JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-1970000000-922a65848e2bfc3f1481JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-5910000000-09cf6f8f89aea7db38a8JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB009572
KNApSAcK IDNot Available
Chemspider ID389080
KEGG Compound IDC03648
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440073
PDB IDNot Available
ChEBI ID17343
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available