Showing Compound Card for Leucopelargonidin (CDB005190)

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Record Information
Version1.0
Created at2020-04-17 19:18:22 UTC
Updated at2020-11-18 16:39:29 UTC
CannabisDB IDCDB005190
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameLeucopelargonidin
DescriptionLeucopelargonidin, also known as goratensidin, 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. Leucopelargonidin (CAS: 520-17-2) is a colourless chemical compound belonging to the family of leucoanthocyanidins. Leucopelargonidin is an extremely weak basic (essentially neutral) 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 ). Leucopelargonidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 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 expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-LeucopelargonidinChEBI
(2R,3S,4S)-3,4-LeucopelargonidinChEBI
3,4-cis-LeucopelargonidineHMDB
(2R,3S,4S)-LeucopelargonidinHMDB
3,4,4',5,7-FlavanpentolHMDB
GoratensidinHMDB
LeucopelargonidineHMDB
LeucopelargonidolHMDB
LeucopelargonidinHMDB
Chemical FormulaC15H14O6
Average Molecular Weight290.27
Monoisotopic Molecular Weight290.079
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
Description 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
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 4-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • 1,2-diol
  • Secondary alcohol
  • Organoheterocyclic compound
  • Ether
  • Polyol
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen 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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLeucopelargonidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-0970000000-3e60660dfaca3137796cSpectrum
Predicted GC-MSLeucopelargonidin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-2100069000-3ce0116528533bd0d171Spectrum
Predicted GC-MSLeucopelargonidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-8b627d02db62b9f1f86c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abc-0950000000-2b74806e03f640f7e7962016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g0-4900000000-59f4d5454c4db4612e0c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-6d8231aab24727e61b962016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-1970000000-922a65848e2bfc3f14812016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-5910000000-09cf6f8f89aea7db38a82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-2d980c515d025d58a6fa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0920000000-c778de7956c2638ac4b92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvu-3910000000-a7264b9a10375865f13c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-4a887fee01b47595208a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0910000000-788fd5f61f426f40a4622021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-181b5d47afc5e25b536c2021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0032322
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB009572
KNApSAcK IDC00020638
Chemspider ID389080
KEGG Compound IDC03648
BioCyc IDLEUCOPELARGONIDIN-CMPD
BiGG IDNot Available
Wikipedia LinkLeucopelargonidin
METLIN IDNot Available
PubChem Compound440073
PDB IDNot Available
ChEBI ID17343
References
General ReferencesNot Available