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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:17:29 UTC

Update Date

2021-09-26 22:51:36 UTC

HMDB ID

HMDB0244101

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,2-Naphthoquinone

Description

1,2-Naphthoquinone, also known as 1,2-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). 1,2-Naphthoquinone 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 a significant number of articles have been published on 1,2-Naphthoquinone. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,2-naphthoquinone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,2-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                                 07-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-14         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    7                                                       
CONECT    6    5    9                                                       
CONECT    7    3    5    8                                                  
CONECT    8    4    7   10                                                  
CONECT    9    6   10   11                                                  
CONECT   10    8    9   12                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dihydro-1,2-diketo-naphthalene	ChEBI
1,2-Dihydronaphthalene-1,2-dione	ChEBI
1,2-Naphthalenedione	ChEBI
beta-Naphthoquinone	ChEBI
O-Naphthoquinone	ChEBI
Ortho-naphthoquinone	ChEBI
b-Naphthoquinone	Generator
Β-naphthoquinone	Generator

Chemical Formula

C₁₀H₆O₂

Average Molecular Weight

158.1534

Monoisotopic Molecular Weight

158.036779436

IUPAC Name

1,2-dihydronaphthalene-1,2-dione

Traditional Name

1,2-naphthoquinone

CAS Registry Number

Not Available

SMILES

O=C1C=CC2=CC=CC=C2C1=O

InChI Identifier

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

InChI Key

KETQAJRQOHHATG-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
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:34055 )
a small molecule (CPD-4895 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Microsome (HMDB: HMDB0244101)
Membrane (HMDB: HMDB0244101)
Membrane (HMDB: HMDB0244101)
Nuclear membrane (HMDB: HMDB0244101)
Extracellular (HMDB: HMDB0244101)
Cytosol (HMDB: HMDB0244101)
Mitochondrial membrane (HMDB: HMDB0244101)

Organelle

Mitochondrion (HMDB: HMDB0244101)
Endoplasmic reticulum (HMDB: HMDB0244101)

Biofluid or Excreta

Biofluid and excreta (HMDB: HMDB0244101)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (HMDB: HMDB0244101)

Biochemical process

Cell cycle (HMDB: HMDB0244101)

Biochemical pathway

Disease pathway

Antifungal Agents (HMDB: HMDB0244101)

Metabolic pathway

Naphthalene Degradation (HMDB: HMDB0244101)

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	1.6	ALOGPS
logP	2.21	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	-8.6	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	46.16 m³·mol⁻¹	ChemAxon
Polarizability	15.48 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+H]+	129.987	30932474
DeepCCS	[M-H]-	126.264	30932474
DeepCCS	[M-2H]-	163.703	30932474
DeepCCS	[M+Na]+	139.174	30932474
AllCCS	[M+H]+	132.5	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	138.1	32859911
AllCCS	[M-H]-	131.0	32859911
AllCCS	[M+Na-2H]-	131.5	32859911
AllCCS	[M+HCOO]-	132.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	5.96 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3073 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.06 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1828.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	444.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	275.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	163.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	450.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	563.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1086.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	379.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1123.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	317.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	450.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	378.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	69.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Naphthoquinone	O=C1C=CC2=CC=CC=C2C1=O	2478.7	Standard polar	33892256
1,2-Naphthoquinone	O=C1C=CC2=CC=CC=C2C1=O	1407.1	Standard non polar	33892256
1,2-Naphthoquinone	O=C1C=CC2=CC=CC=C2C1=O	1520.9	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 - 1,2-Naphthoquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-1900000000-42c8f89b2ecaa0f83a95	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Naphthoquinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0ue9-5900000000-69fae954804ba19712ef	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 - 1,2-Naphthoquinone 10V, Positive-QTOF	splash10-0a4i-0900000000-fdec458a61dbf43aca2e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 20V, Positive-QTOF	splash10-0a4i-0900000000-a25a988c2ca6f8139e4b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 40V, Positive-QTOF	splash10-0zfr-4900000000-f08cdd3ed77583e2d511	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 10V, Negative-QTOF	splash10-0a4i-0900000000-15de94554910b64fef7a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 20V, Negative-QTOF	splash10-0a4i-0900000000-3ad946808075a5b4a874	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 40V, Negative-QTOF	splash10-0pb9-0900000000-97d16db55cbe2217eec6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 10V, Positive-QTOF	splash10-0a4i-0900000000-6d3211f5b01d2864ea9b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 20V, Positive-QTOF	splash10-0a59-0900000000-63a86989a211a2574094	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 40V, Positive-QTOF	splash10-0fb9-9400000000-2b2b703729f00c21ecf9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 10V, Negative-QTOF	splash10-0a4i-0900000000-3f5765b536b8e874a7de	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 20V, Negative-QTOF	splash10-0a4i-0900000000-833b0d0cdbc4ad8a6c16	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 40V, Negative-QTOF	splash10-0a6r-2900000000-69674abdba6e23e4f592	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

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

1,2-Naphthoquinone

METLIN ID

Not Available

PubChem Compound

10667

PDB ID

Not Available

ChEBI ID

34055

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 ]

Enzymes

Enzyme Details

1. Quinone oxidoreductase

General function:: Involved in zinc ion binding
Specific function:: Does not have alcohol dehydrogenase activity. Binds NADP and acts through a one-electron transfer process. Orthoquinones, such as 1,2-naphthoquinone or 9,10-phenanthrenequinone, are the best substrates (in vitro). May act in the detoxification of xenobiotics. Interacts with (AU)-rich elements (ARE) in the 3'-UTR of target mRNA species. Enhances the stability of mRNA coding for BCL2. NADPH binding interferes with mRNA binding.
Gene Name:: CRYZ
Uniprot ID:: Q08257
Molecular weight:: 35206.36

Enzyme Details

2. Aflatoxin B1 aldehyde reductase member 2

General function:: Energy production and conversion
Specific function:: Catalyzes the NADPH-dependent reduction of succinic semialdehyde to gamma-hydroxybutyrate. May have an important role in producing the neuromodulator gamma-hydroxybutyrate (GHB). Has broad substrate specificity. Has NADPH-dependent aldehyde reductase activity towards 2-carboxybenzaldehyde, 2-nitrobenzaldehyde and pyridine-2-aldehyde (in vitro). Can reduce 1,2-naphthoquinone and 9,10-phenanthrenequinone (in vitro). Can reduce the dialdehyde protein-binding form of aflatoxin B1 (AFB1) to the non-binding AFB1 dialcohol. May be involved in protection of liver against the toxic and carcinogenic effects of AFB1, a potent hepatocarcinogen.
Gene Name:: AKR7A2
Uniprot ID:: O43488
Molecular weight:: 39588.65

Showing metabocard for 1,2-Naphthoquinone (HMDB0244101)

MOL for HMDB0244101 (1,2-Naphthoquinone)

3D MOL for HMDB0244101 (1,2-Naphthoquinone)

3D SDF for HMDB0244101 (1,2-Naphthoquinone)

3D-SDF for HMDB0244101 (1,2-Naphthoquinone)

PDB for HMDB0244101 (1,2-Naphthoquinone)

3D PDB for HMDB0244101 (1,2-Naphthoquinone)

SMILES for HMDB0244101 (1,2-Naphthoquinone)

INCHI for HMDB0244101 (1,2-Naphthoquinone)

Structure for HMDB0244101 (1,2-Naphthoquinone)

3D Structure for HMDB0244101 (1,2-Naphthoquinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes