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Showing NP-Card for Aniline (NP0001237)

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Record Information
Version1.0
Created at2006-05-22 15:12:26 UTC
Updated at2021-10-07 20:40:55 UTC
NP-MRD IDNP0001237
Secondary Accession NumbersNone
Natural Product Identification
Common NameAniline
DescriptionAniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th century. Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. In 1834, Friedrich Runge isolated from coal tar a substance which produced a beautiful blue color on treatment with chloride of lime; this he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit, dark-blue.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001237 (Aniline)


  Mrv1652305271900032D          

  7  7  0  0  0  0            999 V2000
   23.2644  -14.6921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2644  -15.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9790  -15.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5500  -15.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9790  -16.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5500  -16.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2644  -17.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
Download

3D MOL for NP0001237 (Aniline)

HMDB0003012
     RDKit          3D
Aniline
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.3099    0.2266   -0.1579 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968    0.0713   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681    1.1697    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3028    1.0806    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9050   -0.1589    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780   -1.2731    0.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2959   -1.1733   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284    1.0238    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8826   -0.4742   -0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5365    2.1545   -0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9428    1.9513    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9812   -0.2985    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5517   -2.2574    0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9434   -2.0425   -0.0956 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  2  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
M  END
Download

3D SDF for NP0001237 (Aniline)


  Mrv1652305271900032D          

  7  7  0  0  0  0            999 V2000
   23.2644  -14.6921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2644  -15.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9790  -15.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5500  -15.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9790  -16.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5500  -16.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2644  -17.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2

> <INCHI_KEY>
PAYRUJLWNCNPSJ-UHFFFAOYSA-N

> <FORMULA>
C6H7N

> <MOLECULAR_WEIGHT>
93.1265

> <EXACT_MASS>
93.057849229

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.285464630322043

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
aniline

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.1443198620000001

> <ALOGPS_LOGS>
-0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.641818038580084

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
30.758399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aniline

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001237 (Aniline)

HMDB0003012
     RDKit          3D
Aniline
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.3099    0.2266   -0.1579 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968    0.0713   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681    1.1697    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3028    1.0806    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9050   -0.1589    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780   -1.2731    0.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2959   -1.1733   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284    1.0238    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8826   -0.4742   -0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5365    2.1545   -0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9428    1.9513    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9812   -0.2985    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5517   -2.2574    0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9434   -2.0425   -0.0956 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  2  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
M  END
Download

PDB for NP0001237 (Aniline)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0      43.427 -27.425   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      43.427 -28.965   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      44.761 -29.735   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      42.093 -29.735   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      44.761 -31.275   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      42.093 -31.275   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      43.427 -32.045   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    7                                                       
CONECT    7    5    6                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
Download

3D PDB for NP0001237 (Aniline)

COMPND    HMDB0003012
HETATM    1  N1  UNL     1       2.310   0.227  -0.158  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.897   0.071  -0.061  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.068   1.170   0.014  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.303   1.081   0.109  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.905  -0.159   0.133  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.078  -1.273   0.058  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.296  -1.173  -0.037  1.00  0.00           C  
HETATM    8  H1  UNL     1       2.828   1.024   0.274  1.00  0.00           H  
HETATM    9  H2  UNL     1       2.883  -0.474  -0.680  1.00  0.00           H  
HETATM   10  H3  UNL     1       0.536   2.155  -0.005  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.943   1.951   0.167  1.00  0.00           H  
HETATM   12  H5  UNL     1      -2.981  -0.299   0.206  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.552  -2.257   0.077  1.00  0.00           H  
HETATM   14  H7  UNL     1       0.943  -2.042  -0.096  1.00  0.00           H  
CONECT    1    2    8    9
CONECT    2    3    3    7
CONECT    3    4   10
CONECT    4    5    5   11
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7   14
END
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SMILES for NP0001237 (Aniline)

NC1=CC=CC=C1
Download

INCHI for NP0001237 (Aniline)

InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
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View in JSmol
Synonyms
ValueSource
AminobenzeneChEBI
AminophenChEBI
AnilinChEBI
BenzenamineChEBI
BenzeneamineChEBI
KyanolChEBI
PhenylamineChEBI
ArylamineKegg
AnilinaHMDB
Aniline hydrobromideHMDB
Aniline reagentHMDB
AnyvimHMDB
BenzidamHMDB
CyanolHMDB
D'AnilineHMDB
KrystallinHMDB
Aniline diphosphate (3:1)HMDB
Aniline hydrogen iodideHMDB
Aniline phosphate (1:2)HMDB
Aniline phosphate (2:1)HMDB
Aniline sulfateHMDB
Aniline, 3-(13)C-labeled CPDHMDB
Aniline aluminium saltHMDB
Aniline diphosphate (4:1)HMDB
Aniline hydrochloride-(15)N-labeled CPDHMDB
Aniline hydrofluorideHMDB
Aniline monosulfateHMDB
Aniline nitrateHMDB
Aniline sulfate (2:1)HMDB
Aniline, 2-(13)C-labeled CPDHMDB
Aniline, conjugate acidHMDB
Aniline, sodium saltHMDB
Aniline dihydrofluorideHMDB
Aniline diphosphate (1:1)HMDB
Aniline hydrochlorideHMDB
Aniline hydrochloride-(14)C-labeled CPDHMDB
Aniline perchlorateHMDB
Aniline phosphonate (1:1)HMDB
Aniline, (13)C-labeled CPDHMDB
Aniline, (14)C-labeled CPDHMDB
Aniline, 4-(13)C-labeled CPDHMDB
Aniline, ion(1+)HMDB
Aniline, monolithium saltHMDB
Aniline phosphate (1:1)HMDB
Aniline sulfate (2:1), (14)C-labeled CPDHMDB
Aniline, 15N-labeled CPDHMDB
Aniline, 3H-labeled CPDHMDB
Aniline, magnesium (1:1) saltHMDB
Chemical FormulaC6H7N
Average Mass93.1265 Da
Monoisotopic Mass93.05785 Da
IUPAC Nameaniline
Traditional Nameaniline
CAS Registry Number62-53-3
SMILES
NC1=CC=CC=C1
InChI Identifier
InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
InChI KeyPAYRUJLWNCNPSJ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium sativumFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apium graveolensFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea var. capitataFooDB
Bubalus bubalisFooDB
Camellia sinensisLOTUS Database
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Malus pumilaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tessmannia densifloraKNApSAcK Database
Trigonella foenum-graecumLOTUS Database
Zea mays L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative Parents
Substituents
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-6 °CNot Available
Boiling Point184.00 to 185.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility36 mg/mL at 25 °CNot Available
LogP0.90Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility18 g/LALOGPS
logP0.89ALOGPS
logP1.14ChemAxon
logS-0.71ALOGPS
pKa (Strongest Basic)4.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.76 m³·mol⁻¹ChemAxon
Polarizability10.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003012
DrugBank IDDB06728
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003571
KNApSAcK IDC00048294
Chemspider ID5889
KEGG Compound IDC00292
BioCyc IDANILINE
BiGG IDNot Available
Wikipedia LinkAniline
METLIN ID489
PubChem Compound6115
PDB IDNot Available
ChEBI ID17296
Good Scents IDrw1220191
References
General References
  1. Bomhard EM, Herbold BA: Genotoxic activities of aniline and its metabolites and their relationship to the carcinogenicity of aniline in the spleen of rats. Crit Rev Toxicol. 2005 Dec;35(10):783-835. [PubMed:16468500 ]
  2. Nohynek GJ, Duche D, Garrigues A, Meunier PA, Toutain H, Leclaire J: Under the skin: Biotransformation of para-aminophenol and para-phenylenediamine in reconstructed human epidermis and human hepatocytes. Toxicol Lett. 2005 Sep 15;158(3):196-212. [PubMed:15890478 ]
  3. Mathews JM, De Costa KS: Absorption, metabolism, and disposition of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v., and dermal administration. Drug Metab Dispos. 1999 Dec;27(12):1499-504. [PubMed:10570033 ]
  4. Weiss T, Angerer J: Simultaneous determination of various aromatic amines and metabolites of aromatic nitro compounds in urine for low level exposure using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Oct 5;778(1-2):179-92. [PubMed:12376125 ]
  5. Hein DW, Doll MA, Xiao GH, Feng Y: Prostate expression of N-acetyltransferase 1 (NAT1) and 2 (NAT2) in rapid and slow acetylator congenic Syrian hamster. Pharmacogenetics. 2003 Mar;13(3):159-67. [PubMed:12618593 ]
  6. Kuo HM, Ho HJ, Chao PD, Chung JG: Quercetin glucuronides inhibited 2-aminofluorene acetylation in human acute myeloid HL-60 leukemia cells. Phytomedicine. 2002 Oct;9(7):625-31. [PubMed:12487326 ]
  7. Faraglia B, Chen SY, Gammon MD, Zhang Y, Teitelbaum SL, Neugut AI, Ahsan H, Garbowski GC, Hibshoosh H, Lin D, Kadlubar FF, Santella RM: Evaluation of 4-aminobiphenyl-DNA adducts in human breast cancer: the influence of tobacco smoke. Carcinogenesis. 2003 Apr;24(4):719-25. [PubMed:12727801 ]
  8. Peluso M, Airoldi L, Magagnotti C, Fiorini L, Munnia A, Hautefeuille A, Malaveille C, Vineis P: White blood cell DNA adducts and fruit and vegetable consumption in bladder cancer. Carcinogenesis. 2000 Feb;21(2):183-7. [PubMed:10657956 ]
  9. el-Bayoumy K, Donahue JM, Hecht SS, Hoffmann D: Identification and quantitative determination of aniline and toluidines in human urine. Cancer Res. 1986 Dec;46(12 Pt 1):6064-7. [PubMed:3779628 ]
  10. Iwersen-Bergmann S, Schmoldt A: Acute intoxication with aniline: detection of acetaminophen as aniline metabolite. Int J Legal Med. 2000;113(3):171-4. [PubMed:10876991 ]
  11. Gan J, Skipper PL, Gago-Dominguez M, Arakawa K, Ross RK, Yu MC, Tannenbaum SR: Alkylaniline-hemoglobin adducts and risk of non-smoking-related bladder cancer. J Natl Cancer Inst. 2004 Oct 6;96(19):1425-31. [PubMed:15467031 ]
  12. Stanley LA, Coroneos E, Cuff R, Hickman D, Ward A, Sim E: Immunochemical detection of arylamine N-acetyltransferase in normal and neoplastic bladder. J Histochem Cytochem. 1996 Sep;44(9):1059-67. [PubMed:8773572 ]
  13. Vaziri SA, Hughes NC, Sampson H, Darlington G, Jewett MA, Grant DM: Variation in enzymes of arylamine procarcinogen biotransformation among bladder cancer patients and control subjects. Pharmacogenetics. 2001 Feb;11(1):7-20. [PubMed:11207033 ]