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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:25:04 UTC
Update Date2019-07-23 07:14:28 UTC
HMDB IDHMDB0060497
Secondary Accession Numbers
  • HMDB60497
Metabolite Identification
Common NameNaphthalene-1,2-diol
DescriptionNaphthalene-1,2-diol, also known as 1,2-naphthalenediol or 1,2-naphthohydroquinone, belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. Naphthalene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). Naphthalene-1,2-diol exists in all living organisms, ranging from bacteria to humans. These are hydroxylated naphthalenes.
Structure
Data?1563866068
Synonyms
ValueSource
1,2-DihydroxynaphthaleneChEBI
1,2-NaphthalenediolChEBI
1,2-NaphthohydroquinoneChEBI
beta-NaphthohydroquinoneChEBI
b-NaphthohydroquinoneGenerator
Β-naphthohydroquinoneGenerator
1,2-Dihydroxynaphthalene monohydrateHMDB
Chemical FormulaC10H8O2
Average Molecular Weight160.1693
Monoisotopic Molecular Weight160.0524295
IUPAC Namenaphthalene-1,2-diol
Traditional Name1,2-dihydroxynaphthalene
CAS Registry NumberNot Available
SMILES
OC1=CC=C2C=CC=CC2=C1O
InChI Identifier
InChI=1S/C10H8O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,11-12H
InChI KeyNXPPAOGUKPJVDI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthols and derivatives
Direct ParentNaphthols and derivatives
Alternative Parents
Substituents
  • 1-naphthol
  • 2-naphthol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

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
Water Solubility0.71 g/LALOGPS
logP2.06ALOGPS
logP2.36ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.04ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.47 m³·mol⁻¹ChemAxon
Polarizability16.4 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.32131661259
DarkChem[M-H]-130.89131661259
DeepCCS[M+H]+130.69730932474
DeepCCS[M-H]-128.14430932474
DeepCCS[M-2H]-164.28130932474
DeepCCS[M+Na]+139.3430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Naphthalene-1,2-diolOC1=CC=C2C=CC=CC2=C1O3045.4Standard polar33892256
Naphthalene-1,2-diolOC1=CC=C2C=CC=CC2=C1O1593.7Standard non polar33892256
Naphthalene-1,2-diolOC1=CC=C2C=CC=CC2=C1O1734.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Naphthalene-1,2-diol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C=CC=CC2=C1O1745.9Semi standard non polar33892256
Naphthalene-1,2-diol,1TMS,isomer #2C[Si](C)(C)OC1=C(O)C=CC2=CC=CC=C121729.6Semi standard non polar33892256
Naphthalene-1,2-diol,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2C=CC=CC2=C1O[Si](C)(C)C1773.1Semi standard non polar33892256
Naphthalene-1,2-diol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC=CC2=C1O1995.1Semi standard non polar33892256
Naphthalene-1,2-diol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O)C=CC2=CC=CC=C121986.5Semi standard non polar33892256
Naphthalene-1,2-diol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC=CC2=C1O[Si](C)(C)C(C)(C)C2288.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Naphthalene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q9-0900000000-0f956a12d0643c144a3c2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naphthalene-1,2-diol GC-MS (2 TMS) - 70eV, Positivesplash10-0fl9-4290000000-a8b5d5f699983fa20c232017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naphthalene-1,2-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 10V, Positive-QTOFsplash10-03di-0900000000-43ad7fe3948f81593f242017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 20V, Positive-QTOFsplash10-03di-0900000000-3f891b94d5d45e2c9ae12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 40V, Positive-QTOFsplash10-0udl-3900000000-4f2b9a1e61aa434bea1b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 10V, Negative-QTOFsplash10-0a4i-0900000000-4f24626a6d139a7f3bac2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 20V, Negative-QTOFsplash10-0a4i-0900000000-738df9d80c446d325a102017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 40V, Negative-QTOFsplash10-0pb9-1900000000-a2f5a34fc929cd1847902017-07-26Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07610
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03012
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11318
PDB IDNot Available
ChEBI ID17435
Food Biomarker OntologyNot Available
VMH ID12NPTHLDL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
DHDH
Uniprot ID:
Q9UQ10
Molecular weight:
36381.705
Reactions
1,2-Dihydronaphthalene-1,2-diol + NADP → Naphthalene-1,2-diol + NADPH + Hydrogen Iondetails