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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:56 UTC
Update Date2019-07-23 06:07:15 UTC
HMDB IDHMDB0030773
Secondary Accession Numbers
  • HMDB30773
Metabolite Identification
Common NameJuglone
DescriptionJuglone, also known as antibiotic PD7 or ci 75500, belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Juglone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Juglone is found, on average, in the highest concentration within a few different foods, such as black walnuts, common walnuts, and liquors. Juglone has also been detected, but not quantified in, butternuts and nuts. This could make juglone a potential biomarker for the consumption of these foods. A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group.
Structure
Data?1563862035
Synonyms
ValueSource
5-Hydroxy-1,4-naphthalenedioneChEBI
5-Hydroxy-1,4-naphthoquinoneChEBI
8-Hydroxy-1,4-naphthoquinoneChEBI
-Hydroxy-1,4-naphthalenedioneHMDB
5-Hydroxy-1,4-naphthalenedione, 9ciHMDB
8-Hydroxy-1,4-naphthalenedioneHMDB
Antibiotic PD7HMDB
C.I. natural brown 7HMDB
CI 75500HMDB
LawsoneHMDB
NucinHMDB
PD7HMDB
RegianinHMDB
Chemical FormulaC10H6O3
Average Molecular Weight174.1528
Monoisotopic Molecular Weight174.031694058
IUPAC Name5-hydroxy-1,4-dihydronaphthalene-1,4-dione
Traditional Namewalnut extract
CAS Registry Number481-39-0
SMILES
OC1=CC=CC2=C1C(=O)C=CC2=O
InChI Identifier
InChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
InChI KeyKQPYUDDGWXQXHS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aryl ketone
  • Quinone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point155 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.92Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.09 g/LALOGPS
logP1.93ALOGPS
logP1.84ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)8.29ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.16 m³·mol⁻¹ChemAxon
Polarizability16.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-0900000000-fb8631f77002311df2c5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5790000000-dfbf4959b881b9285503Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0900000000-2fa9387180114c863fc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0900000000-fefe993c0e30ef03165cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-38ba61c5d0f8f05daf1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-11e27d12e57f1d478761Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00b9-1900000000-3ba233f55939e221f9b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9600000000-534e2b9919a0c9665a82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-78b1f074f70ea780a1efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-78b1f074f70ea780a1efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-5900000000-22cd050139caaab81233Spectrum
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 ID652
FooDB IDFDB002708
KNApSAcK IDC00000144
Chemspider ID3674
KEGG Compound IDC03840
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkJuglone
METLIN IDNot Available
PubChem Compound3806
PDB IDJUG
ChEBI ID15794
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.. .