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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:56 UTC
Update Date2023-02-21 17:19:41 UTC
HMDB IDHMDB0030773
Secondary Accession Numbers
  • HMDB30773
Metabolite Identification
Common NameJuglone
DescriptionJuglone 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 found, on average, in the highest concentration within a few different foods, such as black walnuts (Juglans nigra), common walnuts (Juglans regia), and liquor. Juglone has also been detected, but not quantified in, butternuts (Juglans cinerea) and nuts. This could make juglone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Juglone.
Structure
Data?1676999981
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point155 °CNot Available
Boiling Point385.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility5121 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.92Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker131.20130932474
[M-H]-Not Available131.201http://allccs.zhulab.cn/database/detail?ID=AllCCS00001920
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.04431661259
DarkChem[M-H]-134.96531661259
DeepCCS[M+H]+134.54330932474
DeepCCS[M-H]-131.87430932474
DeepCCS[M-2H]-168.11130932474
DeepCCS[M+Na]+143.48230932474
AllCCS[M+H]+136.032859911
AllCCS[M+H-H2O]+131.532859911
AllCCS[M+NH4]+140.232859911
AllCCS[M+Na]+141.532859911
AllCCS[M-H]-132.732859911
AllCCS[M+Na-2H]-133.032859911
AllCCS[M+HCOO]-133.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
JugloneOC1=CC=CC2=C1C(=O)C=CC2=O2730.0Standard polar33892256
JugloneOC1=CC=CC2=C1C(=O)C=CC2=O1563.3Standard non polar33892256
JugloneOC1=CC=CC2=C1C(=O)C=CC2=O1511.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Juglone,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC2=C1C(=O)C=CC2=O1776.3Semi standard non polar33892256
Juglone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C=CC2=O2092.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Juglone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-0900000000-fb8631f77002311df2c52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Juglone GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5790000000-dfbf4959b881b92855032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Juglone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Juglone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Juglone Linear Ion Trap , positive-QTOFsplash10-0006-0900000000-2fa9387180114c863fc42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Juglone Linear Ion Trap , positive-QTOFsplash10-014i-0900000000-fefe993c0e30ef03165c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Juglone Linear Ion Trap , positive-QTOFsplash10-001i-0900000000-38ba61c5d0f8f05daf1e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 10V, Positive-QTOFsplash10-004i-0900000000-11e27d12e57f1d4787612016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 20V, Positive-QTOFsplash10-00b9-1900000000-3ba233f55939e221f9b02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 40V, Positive-QTOFsplash10-00fr-9600000000-534e2b9919a0c9665a822016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 10V, Negative-QTOFsplash10-00di-0900000000-78b1f074f70ea780a1ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 20V, Negative-QTOFsplash10-00di-0900000000-78b1f074f70ea780a1ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 40V, Negative-QTOFsplash10-00dl-5900000000-22cd050139caaab812332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 10V, Negative-QTOFsplash10-00di-0900000000-8346d407ae6b94e1d8f02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 20V, Negative-QTOFsplash10-00di-0900000000-9104b1a3fa723ef497492021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 40V, Negative-QTOFsplash10-0005-7900000000-ccfb091c3dc53d1d3d952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 10V, Positive-QTOFsplash10-004i-0900000000-b62248e35e3d964671bf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 20V, Positive-QTOFsplash10-004i-0900000000-3647d6281d267b3db1322021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Juglone 40V, Positive-QTOFsplash10-0kmj-5900000000-6c53bc2741b205b21c182021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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 IDNot Available
Good Scents IDrw1210311
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.. .