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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:26:14 UTC

Update Date

2021-09-26 22:59:33 UTC

HMDB ID

HMDB0248973

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzanilide

Description

BENZANILIDE belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene. BENZANILIDE is a moderately basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzanilide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzanilide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306031607182D          

 15 16  0  0  0  0            999 V2000
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  4  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248973

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO/c15-13(11-7-3-1-4-8-11)14-12-9-5-2-6-10-12/h1-10H,(H,14,15)

> <INCHI_KEY>
ZVSKZLHKADLHSD-UHFFFAOYSA-N

> <FORMULA>
C13H11NO

> <MOLECULAR_WEIGHT>
197.237

> <EXACT_MASS>
197.084063978

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.778322337998706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-phenylbenzenecarboximidic acid

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.7925872919999994

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.37309748140945

> <JCHEM_PKA_STRONGEST_BASIC>
1.3656619662801315

> <JCHEM_POLAR_SURFACE_AREA>
32.59

> <JCHEM_REFRACTIVITY>
62.34660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzanilide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12                                                       
CONECT   10    6   12                                                       
CONECT   11    7    8   13                                                  
CONECT   12    9   10   14                                                  
CONECT   13   11   14   15                                                  
CONECT   14   12   13                                                       
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0248973
HETATM    1  O1  UNL     1      -0.112  -1.752  -0.508  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.405  -0.482  -0.296  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.372   0.524  -0.119  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.773   0.462  -0.121  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.466   0.129  -1.257  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.843   0.066  -1.261  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.526   0.341  -0.111  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.846   0.680   1.053  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.473   0.736   1.030  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.843  -0.264  -0.268  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.699  -1.342  -0.457  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.055  -1.111  -0.427  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.560   0.153  -0.215  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.724   1.235  -0.026  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.362   0.991  -0.058  1.00  0.00           C  
HETATM   16  H1  UNL     1      -0.332  -2.405   0.216  1.00  0.00           H  
HETATM   17  H2  UNL     1      -1.940  -0.098  -2.199  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.397  -0.195  -2.151  1.00  0.00           H  
HETATM   19  H4  UNL     1      -5.610   0.297  -0.094  1.00  0.00           H  
HETATM   20  H5  UNL     1      -4.442   0.890   1.941  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.962   1.006   1.963  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.258  -2.307  -0.619  1.00  0.00           H  
HETATM   23  H8  UNL     1       4.708  -1.976  -0.579  1.00  0.00           H  
HETATM   24  H9  UNL     1       5.629   0.311  -0.196  1.00  0.00           H  
HETATM   25  H10 UNL     1       4.129   2.242   0.143  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.723   1.868   0.095  1.00  0.00           H  
CONECT    1    2   16
CONECT    2    3    3   10
CONECT    3    4
CONECT    4    5    5    9
CONECT    5    6   17
CONECT    6    7    7   18
CONECT    7    8   19
CONECT    8    9    9   20
CONECT    9   21
CONECT   10   11   11   15
CONECT   11   12   22
CONECT   12   13   13   23
CONECT   13   14   24
CONECT   14   15   15   25
CONECT   15   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Phenyl-benzamide	ChEMBL
Benzanilide	MeSH
N-Phenylbenzenecarboximidate	Generator

Chemical Formula

C₁₃H₁₁NO

Average Molecular Weight

197.237

Monoisotopic Molecular Weight

197.084063978

IUPAC Name

N-phenylbenzenecarboximidic acid

Traditional Name

benzanilide

CAS Registry Number

Not Available

SMILES

OC(=NC1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H11NO/c15-13(11-7-3-1-4-8-11)14-12-9-5-2-6-10-12/h1-10H,(H,14,15)

InChI Key

ZVSKZLHKADLHSD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Benzanilides

Alternative Parents

Substituents

Benzanilide
Benzoic acid or derivatives
Benzamide
Benzoyl
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.72	ALOGPS
logP	3.79	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	1.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.35 m³·mol⁻¹	ChemAxon
Polarizability	21.78 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	142.942	30932474
DeepCCS	[M-H]-	140.546	30932474
DeepCCS	[M-2H]-	174.421	30932474
DeepCCS	[M+Na]+	149.034	30932474
AllCCS	[M+H]+	147.1	32859911
AllCCS	[M+H-H2O]+	143.0	32859911
AllCCS	[M+NH4]+	150.9	32859911
AllCCS	[M+Na]+	152.0	32859911
AllCCS	[M-H]-	145.5	32859911
AllCCS	[M+Na-2H]-	145.6	32859911
AllCCS	[M+HCOO]-	145.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzanilide	OC(=NC1=CC=CC=C1)C1=CC=CC=C1	2629.7	Standard polar	33892256
Benzanilide	OC(=NC1=CC=CC=C1)C1=CC=CC=C1	1946.4	Standard non polar	33892256
Benzanilide	OC(=NC1=CC=CC=C1)C1=CC=CC=C1	1775.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzanilide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-7900000000-7c75c20ec61c08b88634	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzanilide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzanilide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzanilide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzanilide 35V, Positive-QTOF	splash10-0a4j-0900000000-843b259d306f9e1dcbe6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 10V, Positive-QTOF	splash10-0002-0900000000-4a632dafbe2b539eb46f	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 20V, Positive-QTOF	splash10-0a4j-0900000000-d9b31327bf31faff2c55	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 40V, Positive-QTOF	splash10-056r-9300000000-b67f65fa5c03187c6522	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 10V, Negative-QTOF	splash10-0002-0900000000-832068d113a4c8d549b0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 20V, Negative-QTOF	splash10-0002-2900000000-219fffbd0311ba55d741	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 40V, Negative-QTOF	splash10-004l-9200000000-3059234d94bcba337ebc	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 10V, Positive-QTOF	splash10-0002-0900000000-491ca48869fda5e065b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 20V, Positive-QTOF	splash10-0002-2900000000-46caace5d4cd9ea73aff	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 40V, Positive-QTOF	splash10-004i-9100000000-3238b5f763c7dab38110	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 10V, Negative-QTOF	splash10-0002-0900000000-22e51f36c9b0590eabb9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 20V, Negative-QTOF	splash10-00b9-6900000000-2a89537adef28d25144f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzanilide 40V, Negative-QTOF	splash10-00or-9600000000-13c5271ecfe0fe9e5548	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7168

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Benzanilide (HMDB0248973)

MOL for HMDB0248973 (Benzanilide)

3D MOL for HMDB0248973 (Benzanilide)

3D SDF for HMDB0248973 (Benzanilide)

3D-SDF for HMDB0248973 (Benzanilide)

PDB for HMDB0248973 (Benzanilide)

3D PDB for HMDB0248973 (Benzanilide)

SMILES for HMDB0248973 (Benzanilide)

INCHI for HMDB0248973 (Benzanilide)

Structure for HMDB0248973 (Benzanilide)

3D Structure for HMDB0248973 (Benzanilide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra