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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:10 UTC
Update Date2020-09-27 21:03:51 UTC
HMDB IDHMDB0030808
Secondary Accession Numbers
  • HMDB30808
Metabolite Identification
Common NamePinocembrin
Description(S)-Pinocembrin, also known as dihydrochrysin, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, (S)-pinocembrin is considered to be a flavonoid lipid molecule (S)-Pinocembrin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (S)-Pinocembrin is found, on average, in the highest concentration within mexican oregano (S)-Pinocembrin has also been detected, but not quantified in, pine nuts and prunus (cherry, plum). This could make (S)-pinocembrin a potential biomarker for the consumption of these foods. A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7.
Structure
Data?1601240631
Synonyms
ValueSource
(2S)-PinocembrinChEBI
(S)-2,3-Dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-oneChEBI
(S)-5,7-DihydroxyflavanoneChEBI
5,7-DihydroxyflavanoneChEBI
DihydrochrysinChEBI
Galangin flavanoneChEBI
PinocembrineMeSH, HMDB
(S)-PinocembrinChEBI
(+)-PinocoembrinMeSH
(+)-PinocembrinPhytoBank
Chemical FormulaC15H12O4
Average Molecular Weight256.2534
Monoisotopic Molecular Weight256.073558872
IUPAC Name(2S)-5,7-dihydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namepinocembrin
CAS Registry Number480-39-7
SMILES
OC1=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2/t13-/m0/s1
InChI KeyURFCJEUYXNAHFI-ZDUSSCGKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanones
Alternative Parents
Substituents
  • Flavanone
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point192 - 193 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.85ALOGPS
logP3.14ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.87ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.31 m³·mol⁻¹ChemAxon
Polarizability26.27 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-024i-7359000000-bbe602140f5eb8e64c35Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0553-2490000000-ab0d5fb04a17ac900f46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-da83748cebaf2aff41e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbi-0970000000-4da94433e475e4b0655cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4900000000-2027700d1a9013d79861Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-3e50055087cb60de2aa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0290000000-047a6df1cc7ac9b1ae05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-5910000000-bfc1ff4fa9dc8cd944c8Spectrum
Biological Properties
Cellular Locations
  • Membrane
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
FooDB IDFDB002759
KNApSAcK IDC00000992
Chemspider IDNot Available
KEGG Compound IDC09827
BioCyc IDCPD-6991
BiGG IDNot Available
Wikipedia LinkPinocembrin
METLIN IDNot Available
PubChem Compound68071
PDB IDNot Available
ChEBI ID28157
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Pinocembrin → 3,4,5-trihydroxy-6-[(7-hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-5-yl)oxy]oxane-2-carboxylic aciddetails
Pinocembrin → 3,4,5-trihydroxy-6-[(5-hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]oxane-2-carboxylic aciddetails