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Showing metabocard for 2-Aminonaphthalene (HMDB0041802)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:40:00 UTC
Update Date2019-07-23 06:35:04 UTC
HMDB IDHMDB0041802
Secondary Accession Numbers
  • HMDB41802
Metabolite Identification
Common Name2-Aminonaphthalene
Description2-Aminonaphthalene, also known as beta-naphthylamine or 2-naphthalenamine, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 2-Aminonaphthalene is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on 2-Aminonaphthalene.
Structure
Data?1563863704
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041802 (2-Aminonaphthalene)


  Mrv1652305261923532D          

 11 12  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  8  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11 10  1  0  0  0  0
M  END
Download

3D MOL for HMDB0041802 (2-Aminonaphthalene)

Download
3D SDF for HMDB0041802 (2-Aminonaphthalene)

  Mrv1652305261923532D          

 11 12  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  8  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041802

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC2=CC=CC=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2

> <INCHI_KEY>
JBIJLHTVPXGSAM-UHFFFAOYSA-N

> <FORMULA>
C10H9N

> <MOLECULAR_WEIGHT>
143.1852

> <EXACT_MASS>
143.073499293

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.06190516374202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
naphthalen-2-amine

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.1337966186666666

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.2545589383855145

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
47.208600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β naphthylamine

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for HMDB0041802 (2-Aminonaphthalene)
https://cactus.nci.nih.gov/chemical/structure/NC1=CC2=CC=CC=C2C=C1/file?forma...
 OpenBabel09142113273D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:19})
 20 21  0  0  0  0  0  0  0  0999 V2000
    3.3920    0.6660    0.0008 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770    0.1970    0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0329    1.0954    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    0.6199    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3806    1.5048   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487    1.0099   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8822   -0.3636    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493   -1.2505    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262   -0.7779    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634   -1.6666    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8330   -1.1820   -0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667    1.6201    0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1310    0.0377    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290    2.1575    0.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2145    2.5720   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860    1.6920   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980   -0.7305    0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -2.3125    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3915   -2.7328    0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655   -1.8700   -0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  2  0  0  0  0
  2 11  1  0  0  0  0
  3  4  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 15  1  0  0  0  0
  6  7  2  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  7 17  1  0  0  0  0
  8  9  2  0  0  0  0
  8 18  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 19  1  0  0  0  0
 11 20  1  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0041802 (2-Aminonaphthalene)
HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+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

Download
3D PDB for HMDB0041802 (2-Aminonaphthalene)
COMPND    https://cactus.nci.nih.gov/chemical/structure/NC1=CC2=CC=CC=C2C=C1/file?forma... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  N   UNL     1       3.392   0.666   0.001  1.00  0.00           N  
HETATM    2  C   UNL     1       2.077   0.197   0.001  1.00  0.00           C  
HETATM    3  C   UNL     1       1.033   1.095   0.000  1.00  0.00           C  
HETATM    4  C   UNL     1      -0.289   0.620   0.000  1.00  0.00           C  
HETATM    5  C   UNL     1      -1.381   1.505  -0.001  1.00  0.00           C  
HETATM    6  C   UNL     1      -2.649   1.010  -0.001  1.00  0.00           C  
HETATM    7  C   UNL     1      -2.882  -0.364   0.000  1.00  0.00           C  
HETATM    8  C   UNL     1      -1.849  -1.250   0.001  1.00  0.00           C  
HETATM    9  C   UNL     1      -0.526  -0.778   0.001  1.00  0.00           C  
HETATM   10  C   UNL     1       0.563  -1.667   0.001  1.00  0.00           C  
HETATM   11  C   UNL     1       1.833  -1.182  -0.004  1.00  0.00           C  
HETATM   12  H   UNL     1       3.567   1.620   0.001  1.00  0.00           H  
HETATM   13  H   UNL     1       4.131   0.038   0.005  1.00  0.00           H  
HETATM   14  H   UNL     1       1.229   2.158   0.000  1.00  0.00           H  
HETATM   15  H   UNL     1      -1.214   2.572  -0.001  1.00  0.00           H  
HETATM   16  H   UNL     1      -3.486   1.692  -0.002  1.00  0.00           H  
HETATM   17  H   UNL     1      -3.898  -0.731   0.001  1.00  0.00           H  
HETATM   18  H   UNL     1      -2.046  -2.312   0.002  1.00  0.00           H  
HETATM   19  H   UNL     1       0.392  -2.733   0.002  1.00  0.00           H  
HETATM   20  H   UNL     1       2.666  -1.870  -0.004  1.00  0.00           H  
CONECT    1    2   12   13                                            
CONECT    2    1    3    3   11                                       
CONECT    3    2    2    4   14                                       
CONECT    4    3    5    5    9                                       
CONECT    5    4    4    6   15                                       
CONECT    6    5    7    7   16                                       
CONECT    7    6    6    8   17                                       
CONECT    8    7    9    9   18                                       
CONECT    9    8    8    4   10                                       
CONECT   10    9   11   11   19                                       
CONECT   11   10   10    2   20                                       
CONECT   12    1                                                      
CONECT   13    1                                                      
CONECT   14    3                                                      
CONECT   15    5                                                      
CONECT   16    6                                                      
CONECT   17    7                                                      
CONECT   18    8                                                      
CONECT   19   10                                                      
CONECT   20   11                                                      
MASTER        0    0    0    0    0    0    0    0   20    0   20    0
END

Download
SMILES for HMDB0041802 (2-Aminonaphthalene)
NC1=CC2=CC=CC=C2C=C1
Download
INCHI for HMDB0041802 (2-Aminonaphthalene)
InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
2-NaftilaminaChEBI
2-NaphthalenamineChEBI
2-NaphthylaminChEBI
6-NaphthylamineChEBI
beta-NaftilaminaChEBI
beta-NaphthylaminChEBI
beta-NaphthylamineChEBI
BNAChEBI
b-NaftilaminaGenerator
Β-naftilaminaGenerator
b-NaphthylaminGenerator
Β-naphthylaminGenerator
b-NaphthylamineGenerator
Β-naphthylamineGenerator
2-AminonaftalenHMDB
2-NaftylaminHMDB
2-NaftylamineHMDB
2-NaphthalamineHMDB
2-NaphthylamineHMDB
beta-NaftalaminHMDB
beta-NaftylaminHMDB
beta-NaftyloaminaHMDB
Fast scarlet base bHMDB
Naphthalen-2-amineHMDB
RCRA waste number u168HMDB
USAF CB-22HMDB
2 NaphthylamineHMDB
2 AminonaphthaleneHMDB
beta NaphthylamineHMDB
2-AminonaphthaleneChEBI
Chemical FormulaC10H9N
Average Molecular Weight143.1852
Monoisotopic Molecular Weight143.073499293
IUPAC Namenaphthalen-2-amine
Traditional Nameβ naphthylamine
CAS Registry Number91-59-8
SMILES
NC1=CC2=CC=CC=C2C=C1
InChI Identifier
InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2
InChI KeyJBIJLHTVPXGSAM-UHFFFAOYSA-N
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
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect:
Disposition
Source:
Biological location:
Role
Indirect biological role:
Biological role:
Environmental role:
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point113 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.19 mg/mL at 25 °CNot Available
LogP2.28Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.78 g/LALOGPS
logP2.3ALOGPS
logP2.13ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)4.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.21 m³·mol⁻¹ChemAxon
Polarizability16.06 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties
Collision Cross Sections
NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available128.98631661259  
DarkChem[M-H]-PredictedNot Available127.48831661259  
Retention Indices
Underivatized
Not Available
Derivatized
Not Available
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-0900000000-ecc6ebe23a5149ac29ab2017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-2900000000-ba05510fe794c267d8ff2014-09-20View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum -  75V, Positivesplash10-0006-0900000000-3bf8f62c0092962b97552021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  90V, Positivesplash10-00mo-0900000000-6b5ffaafdf95402a62162021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  30V, Positivesplash10-0006-0900000000-f2a5e8fa4fb64851b8cb2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  15V, Positivesplash10-0006-0900000000-25323b2ac58bb87e247a2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  45V, Positivesplash10-0006-0900000000-5915a9d18f20364e42632021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  60V, Positivesplash10-0006-0900000000-f27ef67ece738ba351542021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-0006-0900000000-a3754f2dae00f59bff442016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-0006-0900000000-a3754f2dae00f59bff442016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0006-1900000000-7f97cf17cf9c604035f92016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-0006-0900000000-3139ad0a41b8c84bdbc82021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0006-0900000000-5f22983ec8ec75c4235d2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-0006-0900000000-3139ad0a41b8c84bdbc82021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0006-0900000000-a6e33405c02f2304cfbe2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0006-0900000000-bd6d778c87db23cece652016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-014i-4900000000-116c74f287b9a1de7adf2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0006-0900000000-e5d0ebf20455b6c0a9532021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-014i-5900000000-93808191814dc1b4eacc2021-09-08View Spectrum
NMR
Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)2014-09-23View 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6790  
KEGG Compound IDC02227  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Naphthylamine  
METLIN IDNot Available
PubChem Compound7057  
PDB IDNot Available
ChEBI ID27878  
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Armeli G: [Kidney neoplasm in a subject exposed to betanaphthylamine]. Med Lav. 1968 Jun-Jul;59(6):450-4. [PubMed:5738992  ] 
  2. Martynenko AG, Romanenko AM, Kartasheva LA: [Effect of liver functional disorders on the development of betanaphthylamine-induced tumors of the bladder in dogs]. Patol Fiziol Eksp Ter. 1973 May-Jun;17(3):55-6. [PubMed:4750976  ] 
  3. Mancuso TF, el-Attar AA: Cohort study of workers exposed to betanaphthylamine and benzidine. J Occup Med. 1967 Jun;9(6):277-85. [PubMed:6026374  ] 
  4. Ma XH, Sun GQ, Zhao YH, Jia XM: [Study on the properties of a novel glycine amino peptidase from Actinomucor elegans]. Sheng Wu Gong Cheng Xue Bao. 2004 Jul;20(4):578-83. [PubMed:15968992  ] 
  5. Bul'bulian MA: [An epidemiological study of the cancer morbidity in persons having industrial contact with carcinogenic amino compounds]. Vopr Onkol. 1991;37(3):275-9. [PubMed:2031321  ]