Showing Compound Juglone (FDB002708)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:29 UTC

Update date

2020-02-24 19:10:36 UTC

Primary ID

FDB002708

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Juglone

Description

Juglone 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 Number

481-39-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
5-Hydroxy-1,4-naphthalenedione	ChEBI
5-Hydroxy-1,4-naphthoquinone	ChEBI
8-Hydroxy-1,4-naphthoquinone	ChEBI
-Hydroxy-1,4-naphthalenedione	HMDB
5-Hydroxy-1,4-naphthalenedione, 9ci	HMDB
8-Hydroxy-1,4-naphthalenedione	HMDB
Antibiotic PD7	HMDB
C.I. natural brown 7	HMDB
CI 75500	HMDB
Lawsone	HMDB
Nucin	HMDB
PD7	HMDB
Regianin	HMDB
5-Hydroxy-1,4-naphthalenedione, 9CI	db_source
C.I. Natural Brown 7	db_source
Juglone	db_source

Predicted Properties

Property	Value	Source
Water Solubility	2.09 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.84	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	8.29	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	48.16 m³·mol⁻¹	ChemAxon
Polarizability	16.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H6O3

IUPAC name

5-hydroxy-1,4-dihydronaphthalene-1,4-dione

InChI Identifier

InChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H

InChI Key

KQPYUDDGWXQXHS-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=CC2=C1C(=O)C=CC2=O

Average Molecular Weight

174.1528

Monoisotopic Molecular Weight

174.031694058

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).

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:15794 )
alpha-Naphthoquinones (C03840 )
a quinone (HYDROXYNAPHTHOQUINONE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 68.97%; H 3.47%; O 27.56%	DFC
Melting Point	Mp 155°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	1.92	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	422 (e 3630) (MeOH)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Juglone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dj-0900000000-fb8631f77002311df2c5	Spectrum
Predicted GC-MS	Juglone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-5790000000-dfbf4959b881b9285503	Spectrum
Predicted GC-MS	Juglone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Juglone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0006-0900000000-2fa9387180114c863fc4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-014i-0900000000-fefe993c0e30ef03165c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0900000000-38ba61c5d0f8f05daf1e	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-11e27d12e57f1d478761	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00b9-1900000000-3ba233f55939e221f9b0	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fr-9600000000-534e2b9919a0c9665a82	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-78b1f074f70ea780a1ef	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-78b1f074f70ea780a1ef	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-5900000000-22cd050139caaab81233	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-8346d407ae6b94e1d8f0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-9104b1a3fa723ef49749	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-7900000000-ccfb091c3dc53d1d3d95	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-b62248e35e3d964671bf	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-3647d6281d267b3db132	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kmj-5900000000-6c53bc2741b205b21c18	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

652

DrugBank ID

Not Available

HMDB ID

HMDB30773

CRC / DFC (Dictionary of Food Compounds) ID

CND93-Z:CND93-Z

EAFUS ID

Not Available

Dr. Duke ID

JUGLONE

BIGG ID

Not Available

KNApSAcK ID

C00000144

HET ID

JUG

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allelochemic			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti dermatophytic			DUKE
anti feedant			DUKE
anti parasitic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
dye	37958		DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
keratolytic			DUKE
pesticide	25944	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 inducer			DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
sternutatory			DUKE