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Showing Compound Juglone (FDB002708)

Record Information
Version1.0
Creation date2010-04-08 22:05:29 UTC
Update date2020-02-24 19:10:36 UTC
Primary IDFDB002708
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). 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.
CAS Number481-39-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
5-Hydroxy-1,4-naphthalenedione, 9CIdb_source
C.I. Natural Brown 7db_source
Juglonedb_source
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
Chemical FormulaC10H6O3
IUPAC name5-hydroxy-1,4-dihydronaphthalene-1,4-dione
InChI IdentifierInChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
InChI KeyKQPYUDDGWXQXHS-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=CC2=C1C(=O)C=CC2=O
Average Molecular Weight174.1528
Monoisotopic Molecular Weight174.031694058
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.97%; H 3.47%; O 27.56%DFC
Melting PointMp 155°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP1.92HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data422 (e 3630) (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSJuglone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dj-0900000000-fb8631f77002311df2c5Spectrum
Predicted GC-MSJuglone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-5790000000-dfbf4959b881b9285503Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0900000000-2fa9387180114c863fc4Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0900000000-fefe993c0e30ef03165cSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-38ba61c5d0f8f05daf1eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-11e27d12e57f1d478761Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00b9-1900000000-3ba233f55939e221f9b0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9600000000-534e2b9919a0c9665a82Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-78b1f074f70ea780a1efSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-78b1f074f70ea780a1efSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-5900000000-22cd050139caaab81233Spectrum
NMRNot Available
ChemSpider ID3674
ChEMBL IDCHEMBL43612
KEGG Compound IDC03840
Pubchem Compound ID3806
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID652
DrugBank IDNot Available
HMDB IDHMDB30773
CRC / DFC (Dictionary of Food Compounds) IDCND93-Z:CND93-Z
EAFUS IDNot Available
Dr. Duke IDJUGLONE
BIGG IDNot Available
KNApSAcK IDC00000144
HET IDJUG
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allelochemicDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti dermatophyticDUKE
anti feedantDUKE
anti parasitic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
dye37958 DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
keratolyticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
quinone-reductase inducerDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
sternutatoryDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.