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Human Metabolome Database Version 3.5

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Showing metabocard for Naphthalene epoxide (HMDB06215)

Record Information
Version 3.5
Creation Date 2007-05-22 11:47:57 -0600
Update Date 2013-02-08 17:14:34 -0700
HMDB ID HMDB06215
Secondary Accession Numbers None
Metabolite Identification
Common Name Naphthalene epoxide
Description Naphthalene epoxide is an epoxide derivative of naphthalene. The toxicity of naphthalene has to do with the Phase I metabolism of this compound by cytochrome P450 monooxygenases. Deactivation of naphthalene involves epoxidation followed by glutathione conjugation and mercapturic acid formation. Naphthalene is stereoselectively metabolized to form (1R,2S)-Naphthalene epoxide and (1S,2R)-Naphthalene epoxide in the presence of CYP1A1 and CYP1A2, CYP2E1,CYP3A4 and CYP2A6. (PMID: 16959878 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (1R,2S)-Naphthalene 1,2-oxide
  2. (1R,2S)-Naphthalene epoxide
  3. (1S,2R)-Naphthalene epoxide
Chemical Formula C10H8O
Average Molecular Weight 144.1699
Monoisotopic Molecular Weight 144.057514878
IUPAC Name 1aH,7aH-naphtho[1,2-b]oxirene
Traditional IUPAC Name 1aH,7aH-naphtho[1,2-b]oxirene
CAS Registry Number 17180-88-0
SMILES O1C2C=CC3=CC=CC=C3C12
InChI Identifier InChI=1S/C10H8O/c1-2-4-8-7(3-1)5-6-9-10(8)11-9/h1-6,9-10H
InChI Key XQIJIALOJPIKGX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Acenes
Sub Class Naphthalenes
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Organic Compounds
  • arene epoxide(ChEBI)
Substituents
  • Dialkyl Ether
  • Oxirane
Direct Parent Naphthalenes
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 42 - 46 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 1.89 ALOGPS
LogP 2.16 ChemAxon
LogS -2.71 ALOGPS
pKa (strongest basic) -4.3 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 9.23 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 43.87 ChemAxon
Polarizability 15.26 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023839
KNApSAcK ID Not Available
Chemspider ID 97165 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID 2299951 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06215 Link_out
Metagene Link HMDB06215 Link_out
METLIN ID Not Available
PubChem Compound 108063 Link_out
PDB ID Not Available
ChEBI ID 52431 Link_out
References
Synthesis Reference Vogel, E.; Klaerner, F. G. 1,2-Naphthalene oxide. Angewandte Chemie, International Edition in English (1968), 7(5), 374-5.
Material Safety Data Sheet (MSDS) Not Available
General References Not Available