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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 21:23:50 UTC
Update Date2021-09-26 22:51:50 UTC
HMDB IDHMDB0244221
Secondary Accession NumbersNone
Metabolite Identification
Common Name1,4-Naphthoquinone
Description1,4-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
Thumb
Synonyms
ValueSource
1,4-Dihydro-1,4-diketonaphthaleneChEBI
1,4-NaphthalenedioneChEBI
1,4-NQChEBI
[1,4]NaphthoquinonChEBI
alpha-NaphthoquinoneChEBI
NaphthoquinoneChEBI
p-NaphthoquinoneChEBI
a-NaphthoquinoneGenerator
Α-naphthoquinoneGenerator
SuccivilMeSH
Chemical FormulaC10H6O2
Average Molecular Weight158.1534
Monoisotopic Molecular Weight158.036779436
IUPAC Name1,4-dihydronaphthalene-1,4-dione
Traditional Namenaphthoquinone
CAS Registry NumberNot 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 KeyFRASJONUBLZVQX-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
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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
logP1.61ALOGPS
logP1.49ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)12.37ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.18 m³·mol⁻¹ChemAxon
Polarizability15.43 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-2H]-167.20130932474
DeepCCS[M+Na]+142.73930932474
AllCCS[M+H]+132.032859911
AllCCS[M+H-H2O]+127.332859911
AllCCS[M+NH4]+136.432859911
AllCCS[M+Na]+137.632859911
AllCCS[M-H]-129.732859911
AllCCS[M+Na-2H]-130.232859911
AllCCS[M+HCOO]-130.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,4-NaphthoquinoneO=C1C=CC(=O)C2=CC=CC=C122403.3Standard polar33892256
1,4-NaphthoquinoneO=C1C=CC(=O)C2=CC=CC=C121373.4Standard non polar33892256
1,4-NaphthoquinoneO=C1C=CC(=O)C2=CC=CC=C121405.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,4-Naphthoquinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-1900000000-c1d8a7cd50dab22436382021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,4-Naphthoquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0zi0-4900000000-aff14fc4ebdec6f27f112014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 10V, Positive-QTOFsplash10-0a4i-0900000000-c91d1d0c196a75db80992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 20V, Positive-QTOFsplash10-0a4i-1900000000-7023e1d6ad6bb601f4af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 40V, Positive-QTOFsplash10-0a4i-9800000000-704e8571b85c1e233d672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 10V, Negative-QTOFsplash10-0a4i-0900000000-8ab4a16729cf8089e2232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 20V, Negative-QTOFsplash10-0a4i-0900000000-8ab4a16729cf8089e2232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 40V, Negative-QTOFsplash10-0a4i-2900000000-6c220c84a505df1ccf102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 10V, Positive-QTOFsplash10-0a4i-0900000000-6d3211f5b01d2864ea9b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 20V, Positive-QTOFsplash10-0a4i-0900000000-2f0324ec6d5eecc4a3332021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 40V, Positive-QTOFsplash10-056r-9800000000-2c096a2117fab889955c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 10V, Negative-QTOFsplash10-0a4i-0900000000-3f5765b536b8e874a7de2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 20V, Negative-QTOFsplash10-0a4i-0900000000-3f5765b536b8e874a7de2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,4-Naphthoquinone 40V, Negative-QTOFsplash10-056r-6900000000-dee23989cd0e111e875b2021-10-12Wishart 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 IDFDB000340
KNApSAcK IDNot Available
Chemspider ID8215
KEGG Compound IDC02617
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27418
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1149171
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 ]