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Human Metabolome Database Version 3.5

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Showing metabocard for 2-Naphthol (HMDB12322)

Record Information
Version 3.5
Creation Date 2009-05-06 04:25:57 -0600
Update Date 2013-02-08 17:28:48 -0700
HMDB ID HMDB12322
Secondary Accession Numbers None
Metabolite Identification
Common Name 2-Naphthol
Description 2-Naphthol is a colorless crystalline solid and an isomer of 1-naphthol, differing by the location of the hydroxyl group on naphthalene. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. 2-Naphthol has several different uses including dyes, pigments, fats, oils, insecticides, pharmaceuticals, perfumes, antiseptics, synthesis of fungicides, and antioxidants for rubber. Detection of 2-Naphthol in urine usually results from long-term persistent exposure to pesticides such as chlorpyrifos, but also due to exposure to naphthalene in older types of mothballs, fires that produce polyaromatic hydrocarbons (PAHs), and tobacco smoke.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Hydroxynaphthalene
  2. 2-Naftol
  3. 2-Naftolo
  4. 2-Naphthalenol
  5. 2-Naphtol
  6. Antioxygene BN
  7. Azogen developer a
  8. beta-Hydroxynaphthalene
  9. beta-Monoxynaphthalene
  10. beta-Naftol
  11. beta-Naftolo
  12. beta-Naphthol
  13. beta-Naphthyl alcohol
  14. beta-Naphthyl hydroxide
  15. beta-Naphtol
  16. beta-Napthol
  17. beta.-Hydroxynaphthalene
  18. Betanaphthol
  19. Developer BN
  20. Hydronaphthol
  21. Isonaphthol
  22. Naphthol b
  23. Trimetin
Chemical Formula C10H8O
Average Molecular Weight 144.1699
Monoisotopic Molecular Weight 144.057514878
IUPAC Name naphthalen-2-ol
Traditional IUPAC Name developer A
CAS Registry Number 135-19-3
SMILES OC1=CC2=CC=CC=C2C=C1
InChI Identifier InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H
InChI Key JWAZRIHNYRIHIV-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Acenes
Sub Class Naphthalenes
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • a small molecule(Cyc)
  • naphthol(ChEBI)
Substituents
  • Phenol
  • Phenol Derivative
Direct Parent Naphthalenes
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 123 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 2.70 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.72 g/L ALOGPS
LogP 2.93 ALOGPS
LogP 2.66 ChemAxon
LogS -2.30 ALOGPS
pKa (strongest acidic) 9.78 ChemAxon
pKa (strongest basic) -5.5 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 44.49 ChemAxon
Polarizability 15.56 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.00183 umol/mmol creatinine Adult (>18 years old) Male Normal Roofers after the work shift.
Urine Detected and Quantified
Article_icon
0.0028 (0.0025-0.0031) umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.0032 (0.0029-0.0038) umol/mmol creatinine Adult (>18 years old) Male Idiopathic infertility 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 FDB000877
KNApSAcK ID Not Available
Chemspider ID 8341 Link_out
KEGG Compound ID C11713 Link_out
BioCyc ID CPD-8131 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12322 Link_out
Metagene Link HMDB12322 Link_out
METLIN ID Not Available
PubChem Compound 8663 Link_out
PDB ID 03V Link_out
ChEBI ID 10432 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available