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Showing metabocard for N-Acetylarylamine (HMDB0001250)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:33 UTC
HMDB IDHMDB0001250
Secondary Accession Numbers
  • HMDB01250
Metabolite Identification
Common NameN-Acetylarylamine
DescriptionN-Acetylarylamine is an odourless solid chemical of leaf or flake-like appearance. It is also known as acetanilide, N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin. N-Acetylarylamine has analgesic and fever-reducing properties; it is in the same class of drugs as acetaminophen (paracetamol). Under the name acetanilid it formerly figured in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately doing damage to the liver and kidneys. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a metabolite of acetanilide and whose use Axelrod and Brodie suggested in the same study.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001250 (N-Acetylarylamine)

  Mrv0541 02231219002D          

 10 10  0  0  0  0            999 V2000
   -0.2813    0.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866   -0.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352   -0.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    0.8253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866   -1.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352   -1.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165    1.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2813   -1.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1217    0.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165    2.0145    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
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
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3D MOL for HMDB0001250 (N-Acetylarylamine)

HMDB0001250
     RDKit          3D
N-Acetylarylamine
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.5146    0.2251   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512    0.1414    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506    0.1644    1.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    0.0390   -0.5423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3338   -0.0509   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3377   -0.1469   -1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673   -0.2377   -0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943   -0.2380    0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -0.1464    1.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -0.0539    1.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    0.8250   -1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1991    0.7361    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9200   -0.7839   -0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1812    0.0241   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245   -0.1486   -2.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335   -0.3114   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.3081    0.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4441   -0.1423    2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789    0.0175    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
M  END
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3D SDF for HMDB0001250 (N-Acetylarylamine)

  Mrv0541 02231219002D          

 10 10  0  0  0  0            999 V2000
   -0.2813    0.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866   -0.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352   -0.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    0.8253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866   -1.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352   -1.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165    1.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2813   -1.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1217    0.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165    2.0145    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
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001250

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)

> <INCHI_KEY>
FZERHIULMFGESH-UHFFFAOYSA-N

> <FORMULA>
C8H9NO

> <MOLECULAR_WEIGHT>
135.1632

> <EXACT_MASS>
135.068413915

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
14.522900464189632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-phenylacetamide

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
1.2109561833333333

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.376039687049719

> <JCHEM_PKA_STRONGEST_BASIC>
-4.385291195860851

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
40.921

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetanilide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0001250 (N-Acetylarylamine)

HMDB0001250
     RDKit          3D
N-Acetylarylamine
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.5146    0.2251   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512    0.1414    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506    0.1644    1.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    0.0390   -0.5423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3338   -0.0509   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3377   -0.1469   -1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673   -0.2377   -0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943   -0.2380    0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -0.1464    1.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -0.0539    1.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    0.8250   -1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1991    0.7361    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9200   -0.7839   -0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1812    0.0241   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245   -0.1486   -2.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335   -0.3114   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.3081    0.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4441   -0.1423    2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789    0.0175    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
M  END
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PDB for HMDB0001250 (N-Acetylarylamine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.525   0.014   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.842  -0.749   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.812  -0.749   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -0.532   1.541   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -1.842  -2.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.812  -2.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.777   2.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.525  -3.067   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.094   1.527   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.777   3.760   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    8                                                       
CONECT    7    4    9   10                                                  
CONECT    8    5    6                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0001250 (N-Acetylarylamine)

COMPND    HMDB0001250
HETATM    1  C1  UNL     1       3.515   0.225  -0.363  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.151   0.141   0.281  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.051   0.164   1.521  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.026   0.039  -0.542  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.334  -0.051  -0.156  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.338  -0.147  -1.129  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.667  -0.238  -0.869  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.094  -0.238   0.439  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.162  -0.146   1.445  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.795  -0.054   1.140  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.459   0.825  -1.298  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.199   0.736   0.345  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.920  -0.784  -0.523  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.181   0.024  -1.610  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.024  -0.149  -2.168  1.00  0.00           H  
HETATM   16  H6  UNL     1      -3.433  -0.311  -1.628  1.00  0.00           H  
HETATM   17  H7  UNL     1      -4.131  -0.308   0.669  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.444  -0.142   2.490  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.079   0.017   1.958  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5   14
CONECT    5    6    6   10
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   19
END
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SMILES for HMDB0001250 (N-Acetylarylamine)

CC(=O)NC1=CC=CC=C1
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INCHI for HMDB0001250 (N-Acetylarylamine)

InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
AcetamidobenzeneChEBI
AcetanilChEBI
AcetanilidChEBI
AcetanilideChEBI
Acetic acid anilideChEBI
N-AcetylaminobenzeneChEBI
N-PhenylacetamideKegg
Acetate anilideGenerator
AntifebrinHMDB
N-AcetylarylamineChEBI
Chemical FormulaC8H9NO
Average Molecular Weight135.1632
Monoisotopic Molecular Weight135.068413915
IUPAC NameN-phenylacetamide
Traditional Nameacetanilide
CAS Registry Number55576-55-1
SMILES
CC(=O)NC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
InChI KeyFZERHIULMFGESH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.39 mg/mL at 25 °CNot Available
LogP1.16HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg124.16730932474
[M-H]-Not Available124.167http://allccs.zhulab.cn/database/detail?ID=AllCCS00000296
[M+H]+Not Available124.994http://allccs.zhulab.cn/database/detail?ID=AllCCS00000296
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB022512
KNApSAcK IDNot Available
Chemspider ID880
KEGG Compound IDC07565
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Phenylacetamide
METLIN ID6107
PubChem Compound904
PDB IDNot Available
ChEBI ID28884
Food Biomarker OntologyNot Available
VMH IDM01251
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. Arylamine N-acetyltransferase 1
General function:
Involved in acetyltransferase activity
Specific function:
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:
NAT1
Uniprot ID:
P18440
Molecular weight:
33898.445
Enzyme Details
2. Arylamine N-acetyltransferase 2
General function:
Involved in acetyltransferase activity
Specific function:
Not Available
Gene Name:
NAT2
Uniprot ID:
A4Z6T7
Molecular weight:
33570.2