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Showing metabocard for 2-Naphthol (HMDB0012322)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-05-06 10:25:57 UTC
Update Date2023-02-21 17:17:48 UTC
HMDB IDHMDB0012322
Secondary Accession Numbers
  • HMDB12322
Metabolite Identification
Common Name2-Naphthol
Description2-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
Data?1676999868
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012322 (2-Naphthol)

  Mrv1652309042000362D          

 11 12  0  0  0  0            999 V2000
    9.2464   -4.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2464   -4.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9609   -3.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9609   -5.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3901   -3.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1040   -4.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3901   -5.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6754   -4.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6754   -4.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1040   -4.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8185   -5.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0012322 (2-Naphthol)

HMDB0012322
     RDKit          3D
2-Naphthol
 19 20  0  0  0  0  0  0  0  0999 V2000
   -3.5508   -0.5715   -0.5825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398   -0.1268   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679    1.1949   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917    1.6385    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528    0.7373    0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6655    1.1436    0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6838    0.2150    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4581   -1.1172    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1629   -1.5079   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272   -0.5801   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1764   -1.0029   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0528   -0.8776    0.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628    1.9142   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398    2.6593    0.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8316    2.1831    0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114    0.5071    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2858   -1.8403   -0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9429   -2.5345   -0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401   -2.0341   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  2  1  0
 10  5  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
Download

3D SDF for HMDB0012322 (2-Naphthol)

  Mrv1652309042000362D          

 11 12  0  0  0  0            999 V2000
    9.2464   -4.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2464   -4.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9609   -3.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9609   -5.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3901   -3.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1040   -4.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3901   -5.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6754   -4.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6754   -4.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1040   -4.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8185   -5.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012322

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C10H8O

> <MOLECULAR_WEIGHT>
144.1699

> <EXACT_MASS>
144.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.559345473005388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
naphthalen-2-ol

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.659157251

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.783223915102297

> <JCHEM_PKA_STRONGEST_BASIC>
-5.496884912813386

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
44.4891

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β naphthol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0012322 (2-Naphthol)

HMDB0012322
     RDKit          3D
2-Naphthol
 19 20  0  0  0  0  0  0  0  0999 V2000
   -3.5508   -0.5715   -0.5825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398   -0.1268   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679    1.1949   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917    1.6385    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528    0.7373    0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6655    1.1436    0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6838    0.2150    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4581   -1.1172    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1629   -1.5079   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272   -0.5801   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1764   -1.0029   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0528   -0.8776    0.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628    1.9142   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398    2.6593    0.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8316    2.1831    0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114    0.5071    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2858   -1.8403   -0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9429   -2.5345   -0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401   -2.0341   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  2  1  0
 10  5  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
Download

PDB for HMDB0012322 (2-Naphthol)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      17.260  -7.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.260  -9.311   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.594  -7.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.594 -10.081   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.262  -7.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.594  -7.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.262 -10.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.927  -7.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.927  -9.311   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.594  -9.311   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      23.928 -10.081   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    8                                                       
CONECT    4    2    9                                                       
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7    9   10                                                       
CONECT    8    3    5    9                                                  
CONECT    9    4    7    8                                                  
CONECT   10    6    7   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for HMDB0012322 (2-Naphthol)

COMPND    HMDB0012322
HETATM    1  O1  UNL     1      -3.551  -0.571  -0.582  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.240  -0.127  -0.341  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.968   1.195  -0.055  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.692   1.638   0.182  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.353   0.737   0.134  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.666   1.144   0.368  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.684   0.215   0.312  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.458  -1.117   0.029  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.163  -1.508  -0.200  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.127  -0.580  -0.146  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.176  -1.003  -0.382  1.00  0.00           C  
HETATM   12  H1  UNL     1      -4.053  -0.878   0.241  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.763   1.914  -0.011  1.00  0.00           H  
HETATM   14  H3  UNL     1      -0.440   2.659   0.408  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.832   2.183   0.588  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.711   0.507   0.490  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.286  -1.840  -0.011  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.943  -2.535  -0.424  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.340  -2.034  -0.600  1.00  0.00           H  
CONECT    1    2   12
CONECT    2    3    3   11
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6   10
CONECT    6    7    7   15
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   18
CONECT   10   11   11
CONECT   11   19
END
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SMILES for HMDB0012322 (2-Naphthol)

OC1=CC2=CC=CC=C2C=C1
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INCHI for HMDB0012322 (2-Naphthol)

InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H8O
Average Molecular Weight144.1699
Monoisotopic Molecular Weight144.057514878
IUPAC Namenaphthalen-2-ol
Traditional Nameβ naphthol
CAS Registry Number135-19-3
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 KeyJWAZRIHNYRIHIV-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
  • 2-naphthol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point123 °CNot Available
Boiling Point285.00 to 286.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility755 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP2.70HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
UrineDetected and Quantified0.00183 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.00183 umol/mmol creatinineAdult (>18 years old)MaleRoofers (post shift) details
UrineDetected and Quantified0.0028 (0.0025-0.0031) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.00315 (0.00278-0.00357) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
 details
UrineDetected and Quantified0.00259 (0.00234-0.00293) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0032 (0.0029-0.0038) umol/mmol creatinineAdult (>18 years old)MaleIdiopathic infertility details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000877
KNApSAcK IDC00052877
Chemspider ID8341
KEGG Compound IDC11713
BioCyc IDCPD-8131
BiGG IDNot Available
Wikipedia Link2-Naphthol
METLIN IDNot Available
PubChem Compound8663
PDB ID03V
ChEBI ID10432
Food Biomarker OntologyNot Available
VMH IDM00668
MarkerDB IDMDB00029788
Good Scents IDrw1057991
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. COLOMB D, TISSOT A: [2nd Case of dermatitis from betanaphthol with reticular reactions]. Lyon Med. 1956 Nov 4;88(45):423-4. [PubMed:13386410 ]
  2. PATTERSON SJ, LERRIGO AF: Betanaphthol in gelatin capsules; its use as a preservative, with a method for its determination. Q J Pharm Pharmacol. 1947 Apr-Jun;20(2):83-6. [PubMed:20260560 ]
  3. VORONEOV II: [Effect of temperature in the sulphonating of betanaphtol for production of 2,6,8-naphtaldisulphonic acid]. Zhurnal Prikl Him. 1947 May;20(5):464-6. [PubMed:18856458 ]