(1R,2S)-Naphthalene 1,2-oxide (ECMDB20001) (M2MDB000850)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (892)
Record Information
Version2.0
Creation Date2012-05-31 14:22:13 -0600
Update Date2015-09-18 13:44:02 -0600
Secondary Accession Numbers
  • ECMDB20001
Identification
Name:(1R,2S)-Naphthalene 1,2-oxide
Description(1r,2s)-naphthalene 1,2-oxide belongs to the class of Naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (1R,2S)-Naphthalene epoxide
  • (1R,2S,4R)-(+)-borneol
  • 1a,7b-dihydro-(1AS,7BR)-naphth(1,2-b)oxirene
  • 1alpha,7beta-dihydro-(1aS,7bR)-Naphth(1,2-b)oxirene
  • 1α,7β-dihydro-(1AS,7BR)-naphth(1,2-b)oxirene
  • Borneocamphor
  • D-borneol
  • Endo-2-bornanol
  • Sumatra camphor
Chemical Formula:C10H8O
Weight:Average: 144.1699
Monoisotopic: 144.057514878
InChI Key:XQIJIALOJPIKGX-UHFFFAOYSA-N
InChI:InChI=1S/C10H8O/c1-2-4-8-7(3-1)5-6-9-10(8)11-9/h1-6,9-10H
CAS number:73136-20-6
IUPAC Name:(1aR,7aS)-1aH,7aH-naphtho[1,2-b]oxirene
Traditional IUPAC Name:(1aR,7aS)-1aH,7aH-naphtho[1,2-b]oxirene
SMILES:O1C2C=CC3=CC=CC=C3C12
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP1.89ALOGPS
logP2.16ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.87 m³·mol⁻¹ChemAxon
Polarizability15.26 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
(1R,2S)-Naphthalene 1,2-oxide + Glutathione <> (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene
Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene
Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene
Glutathione + Naphthalene epoxide + (1R,2S)-Naphthalene 1,2-oxide > (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene
SMPDB Pathways:
Glutathione metabolismPW000833 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-8e17fcee1e69025d7b19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-5b1ddedd928252655953View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-9700000000-1e74dedc14082f2542dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-82c24c2437621729b2dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-1f87d4685bd2dc480922View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxu-1900000000-1566ad7e8623ac3f4b54View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID33998
HMDB IDHMDB06215
Pubchem Compound ID155957
Kegg IDC14786
ChemSpider ID137368
Wikipedia IDNot Available
BioCyc IDCPD-1903
EcoCyc IDCPD-1903

Enzymes

Protein Details
1. Glutathione S-transferase
General function:
Involved in protein binding
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles
Gene Name:
gst
Uniprot ID:
P0A9D2
Molecular weight:
22868
Reactions
RX + glutathione = HX + R-S-glutathione.
Protein Details
2. GSH-dependent disulfide bond oxidoreductase
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfcG
Uniprot ID:
P77526
Molecular weight:
Not Available