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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 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.
CAS Number481-39-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
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
Predicted GC-MSJuglone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSJuglone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0900000000-2fa9387180114c863fc42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0900000000-fefe993c0e30ef03165c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-38ba61c5d0f8f05daf1e2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-11e27d12e57f1d4787612016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00b9-1900000000-3ba233f55939e221f9b02016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9600000000-534e2b9919a0c9665a822016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-78b1f074f70ea780a1ef2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-78b1f074f70ea780a1ef2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-5900000000-22cd050139caaab812332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-8346d407ae6b94e1d8f02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-9104b1a3fa723ef497492021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-7900000000-ccfb091c3dc53d1d3d952021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-b62248e35e3d964671bf2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-3647d6281d267b3db1322021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmj-5900000000-6c53bc2741b205b21c182021-09-25View Spectrum
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
AllelochemicA chemical released by plants that interacts with other organisms, influencing their behavior or growth. Its biological role involves plant defense and communication. Therapeutically, allelochemics have anti-inflammatory, antimicrobial, and antioxidant properties, with applications in managing anxiety, pain, and infections, as well as potential anticancer uses.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti dermatophyticAn agent that inhibits the growth of dermatophytes, a type of fungus that causes skin, hair, and nail infections, commonly used to treat conditions such as ringworm, athlete's foot, and onychomycosis.DUKE
Anti feedantA substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.DUKE
Anti-parasitic33281 An agent that kills or inhibits the growth of parasites, used to treat infections caused by protozoa, helminths, and ectoparasites, with therapeutic applications in managing diseases such as malaria, toxoplasmosis, and hookworm infections.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Dye37958 A coloring agent with various biological roles, therapeutic applications, and medical uses, including diagnostic imaging, photodynamic therapy, and wound healing, while also serving as a contrast agent to enhance visualization in medical imaging procedures.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
KeratolyticAn agent that breaks down excess skin cells, removing warts and other lesions. It plays a biological role in regulating epidermal growth. Therapeutically, it's used to treat hyperkeratotic conditions. Key medical uses include managing warts, calluses, and ichthyosis, promoting skin smoothing and renewal.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Quinone-reductase inducerAn agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
SternutatoryAn agent that induces sneezing, playing a biological role in expelling irritants from the nasal cavity. Therapeutically, it has applications in relieving nasal congestion and testing olfactory function. Key medical uses include diagnosing and treating nasal and respiratory conditions, such as rhinitis and sinusitis.DUKE
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.