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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:23:50 UTC

Update Date

2021-09-26 22:51:50 UTC

HMDB ID

HMDB0244221

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,4-Naphthoquinone

Description

1,4-Naphtoquinone, also known as alpha-naphthoquinone or 1,4-naphthalenedione, 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). 1,4-Naphtoquinone is found, on average, in the highest concentration within liquor. This could make 1,4-naphtoquinone a potential biomarker for the consumption of these foods. 1,4-Naphtoquinone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 1,4-Naphtoquinone. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,4-naphthoquinone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,4-Naphthoquinone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 24-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1,4-Naphtoquinone                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-SEP-17         0                                  
HETATM    1  O   UNK     0       4.414  -3.080   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.414   3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.747   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.747  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.124   1.593   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.124  -1.593   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.519  -0.802   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.519   0.802   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    5                                                            
CONECT    3    4    5    7                                                  
CONECT    4    3    6    8                                                  
CONECT    5    2    3    9                                                  
CONECT    6    1    4   10                                                  
CONECT    7    3   12                                                       
CONECT    8    4   11                                                       
CONECT    9    5   10                                                       
CONECT   10    6    9                                                       
CONECT   11    8   12                                                       
CONECT   12    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-Dihydro-1,4-diketonaphthalene	ChEBI
1,4-Naphthalenedione	ChEBI
1,4-NQ	ChEBI
[1,4]Naphthoquinon	ChEBI
alpha-Naphthoquinone	ChEBI
Naphthoquinone	ChEBI
p-Naphthoquinone	ChEBI
a-Naphthoquinone	Generator
Α-naphthoquinone	Generator
Succivil	MeSH

Chemical Formula

C₁₀H₆O₂

Average Molecular Weight

158.1534

Monoisotopic Molecular Weight

158.036779436

IUPAC Name

1,4-dihydronaphthalene-1,4-dione

Traditional Name

naphthoquinone

CAS Registry Number

Not Available

SMILES

O=C1C=CC(=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H

InChI Key

FRASJONUBLZVQX-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).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:27418 )
a small molecule (CPD0-954 )

Ontology

Not Available

Liquor (FooDB: FOOD00616)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.61	ALOGPS
logP	1.49	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.18 m³·mol⁻¹	ChemAxon
Polarizability	15.43 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	167.201	30932474
DeepCCS	[M+Na]+	142.739	30932474
AllCCS	[M+H]+	132.0	32859911
AllCCS	[M+H-H2O]+	127.3	32859911
AllCCS	[M+NH4]+	136.4	32859911
AllCCS	[M+Na]+	137.6	32859911
AllCCS	[M-H]-	129.7	32859911
AllCCS	[M+Na-2H]-	130.2	32859911
AllCCS	[M+HCOO]-	130.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,4-Naphthoquinone	O=C1C=CC(=O)C2=CC=CC=C12	2403.3	Standard polar	33892256
1,4-Naphthoquinone	O=C1C=CC(=O)C2=CC=CC=C12	1373.4	Standard non polar	33892256
1,4-Naphthoquinone	O=C1C=CC(=O)C2=CC=CC=C12	1405.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4-Naphthoquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-1900000000-c1d8a7cd50dab2243638	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4-Naphthoquinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0zi0-4900000000-aff14fc4ebdec6f27f11	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 10V, Positive-QTOF	splash10-0a4i-0900000000-c91d1d0c196a75db8099	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 20V, Positive-QTOF	splash10-0a4i-1900000000-7023e1d6ad6bb601f4af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 40V, Positive-QTOF	splash10-0a4i-9800000000-704e8571b85c1e233d67	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 10V, Negative-QTOF	splash10-0a4i-0900000000-8ab4a16729cf8089e223	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 20V, Negative-QTOF	splash10-0a4i-0900000000-8ab4a16729cf8089e223	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 40V, Negative-QTOF	splash10-0a4i-2900000000-6c220c84a505df1ccf10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 10V, Positive-QTOF	splash10-0a4i-0900000000-6d3211f5b01d2864ea9b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 20V, Positive-QTOF	splash10-0a4i-0900000000-2f0324ec6d5eecc4a333	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 40V, Positive-QTOF	splash10-056r-9800000000-2c096a2117fab889955c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 10V, Negative-QTOF	splash10-0a4i-0900000000-3f5765b536b8e874a7de	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 20V, Negative-QTOF	splash10-0a4i-0900000000-3f5765b536b8e874a7de	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 40V, Negative-QTOF	splash10-056r-6900000000-dee23989cd0e111e875b	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000340

KNApSAcK ID

Not Available

Chemspider ID

8215

KEGG Compound ID

C02617

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

27418

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1149171

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 1,4-Naphthoquinone (HMDB0244221)

MOL for HMDB0244221 (1,4-Naphthoquinone)

3D MOL for HMDB0244221 (1,4-Naphthoquinone)

3D SDF for HMDB0244221 (1,4-Naphthoquinone)

3D-SDF for HMDB0244221 (1,4-Naphthoquinone)

PDB for HMDB0244221 (1,4-Naphthoquinone)

3D PDB for HMDB0244221 (1,4-Naphthoquinone)

SMILES for HMDB0244221 (1,4-Naphthoquinone)

INCHI for HMDB0244221 (1,4-Naphthoquinone)

Structure for HMDB0244221 (1,4-Naphthoquinone)

3D Structure for HMDB0244221 (1,4-Naphthoquinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra