Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 21:17:29 UTC
Update Date2021-09-26 22:51:36 UTC
HMDB IDHMDB0244101
Secondary Accession NumbersNone
Metabolite Identification
Common Name1,2-Naphthoquinone
Description1,2-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
Thumb
Synonyms
ValueSource
1,2-Dihydro-1,2-diketo-naphthaleneChEBI
1,2-Dihydronaphthalene-1,2-dioneChEBI
1,2-NaphthalenedioneChEBI
beta-NaphthoquinoneChEBI
O-NaphthoquinoneChEBI
Ortho-naphthoquinoneChEBI
b-NaphthoquinoneGenerator
Β-naphthoquinoneGenerator
Chemical FormulaC10H6O2
Average Molecular Weight158.1534
Monoisotopic Molecular Weight158.036779436
IUPAC Name1,2-dihydronaphthalene-1,2-dione
Traditional Name1,2-naphthoquinone
CAS Registry NumberNot 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 KeyKETQAJRQOHHATG-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
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.6ALOGPS
logP2.21ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)-8.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.16 m³·mol⁻¹ChemAxon
Polarizability15.48 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+129.98730932474
DeepCCS[M-H]-126.26430932474
DeepCCS[M-2H]-163.70330932474
DeepCCS[M+Na]+139.17430932474
AllCCS[M+H]+132.532859911
AllCCS[M+H-H2O]+127.832859911
AllCCS[M+NH4]+136.832859911
AllCCS[M+Na]+138.132859911
AllCCS[M-H]-131.032859911
AllCCS[M+Na-2H]-131.532859911
AllCCS[M+HCOO]-132.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,2-NaphthoquinoneO=C1C=CC2=CC=CC=C2C1=O2478.7Standard polar33892256
1,2-NaphthoquinoneO=C1C=CC2=CC=CC=C2C1=O1407.1Standard non polar33892256
1,2-NaphthoquinoneO=C1C=CC2=CC=CC=C2C1=O1520.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Naphthoquinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-1900000000-42c8f89b2ecaa0f83a952021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Naphthoquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ue9-5900000000-69fae954804ba19712ef2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 10V, Positive-QTOFsplash10-0a4i-0900000000-fdec458a61dbf43aca2e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 20V, Positive-QTOFsplash10-0a4i-0900000000-a25a988c2ca6f8139e4b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 40V, Positive-QTOFsplash10-0zfr-4900000000-f08cdd3ed77583e2d5112016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 10V, Negative-QTOFsplash10-0a4i-0900000000-15de94554910b64fef7a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 20V, Negative-QTOFsplash10-0a4i-0900000000-3ad946808075a5b4a8742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 40V, Negative-QTOFsplash10-0pb9-0900000000-97d16db55cbe2217eec62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 10V, Positive-QTOFsplash10-0a4i-0900000000-6d3211f5b01d2864ea9b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 20V, Positive-QTOFsplash10-0a59-0900000000-63a86989a211a25740942021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 40V, Positive-QTOFsplash10-0fb9-9400000000-2b2b703729f00c21ecf92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 10V, Negative-QTOFsplash10-0a4i-0900000000-3f5765b536b8e874a7de2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 20V, Negative-QTOFsplash10-0a4i-0900000000-833b0d0cdbc4ad8a6c162021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Naphthoquinone 40V, Negative-QTOFsplash10-0a6r-2900000000-69674abdba6e23e4f5922021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00020117
Chemspider ID10217
KEGG Compound IDC14783
BioCyc IDCPD-4895
BiGG IDNot Available
Wikipedia Link1,2-Naphthoquinone
METLIN IDNot Available
PubChem Compound10667
PDB IDNot Available
ChEBI ID34055
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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

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
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