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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:26:59 UTC

Update Date

2021-09-26 23:13:51 UTC

HMDB ID

HMDB0257459

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Salicylanilide

Description

salicylanilide, also known as salinide, 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. Based on a literature review a significant number of articles have been published on salicylanilide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Salicylanilide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Salicylanilide 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


  Mrv0541 05041411132D          

 16 17  0  0  0  0            999 V2000
   -0.0000    3.3000    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
   -0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    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
   -0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   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
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  4  0  0  0
 14 13  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257459

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=NC1=CC=CC=C1)C1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO2/c15-12-9-5-4-8-11(12)13(16)14-10-6-2-1-3-7-10/h1-9,15H,(H,14,16)

> <INCHI_KEY>
WKEDVNSFRWHDNR-UHFFFAOYSA-N

> <FORMULA>
C13H11NO2

> <MOLECULAR_WEIGHT>
213.2319

> <EXACT_MASS>
213.078978601

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.532137785433363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-N-phenylbenzene-1-carboximidic acid

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
4.139021970333333

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.598260921112697

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.473925526115248

> <JCHEM_PKA_STRONGEST_BASIC>
0.8039119237557404

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
64.32750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-N-phenylbenzenecarboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   10                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12                                                       
CONECT   10    6    7   14                                                  
CONECT   11    8   12   13                                                  
CONECT   12    9   11   15                                                  
CONECT   13   11   14   16                                                  
CONECT   14   10   13                                                       
CONECT   15   12                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0257459
HETATM    1  O1  UNL     1      -0.432   1.236   1.295  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.277   0.486   0.352  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.255  -0.497  -0.258  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.582  -0.954  -0.078  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.886  -2.137   0.563  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.191  -2.557   0.723  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.258  -1.820   0.254  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.959  -0.637  -0.388  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.653  -0.219  -0.547  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.647   0.850   0.074  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.180   1.930   0.765  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.480   2.325   0.544  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.289   1.676  -0.357  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.783   0.612  -1.047  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.447   0.198  -0.827  1.00  0.00           C  
HETATM   16  O2  UNL     1       2.008  -0.869  -1.548  1.00  0.00           O  
HETATM   17  H1  UNL     1      -1.232   1.790   1.078  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.044  -2.711   0.929  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.402  -3.501   1.237  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.271  -2.174   0.394  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.809  -0.065  -0.753  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.462   0.722  -1.060  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.558   2.468   1.492  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.855   3.170   1.104  1.00  0.00           H  
HETATM   25  H9  UNL     1       5.312   1.988  -0.531  1.00  0.00           H  
HETATM   26  H10 UNL     1       4.392   0.077  -1.765  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.206  -1.387  -1.645  1.00  0.00           H  
CONECT    1    2   17
CONECT    2    3    3   10
CONECT    3    4
CONECT    4    5    5    9
CONECT    5    6   18
CONECT    6    7    7   19
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   22
CONECT   10   11   11   15
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   14   25
CONECT   14   15   15   26
CONECT   15   16
CONECT   16   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-N-phenylbenzamide	ChEBI
2-N-Phenylcarboxamidophenol	ChEBI
N-Phenylsalicylamide	ChEBI
O-Hydroxybenzanilide	ChEBI
Salicylic acid anilide	ChEBI
Salinide	ChEBI
Salicylate anilide	Generator
Salicylanilide, zinc salt	MeSH
Salicylanilide, sodium salt	MeSH

Chemical Formula

C₁₃H₁₁NO₂

Average Molecular Weight

213.2319

Monoisotopic Molecular Weight

213.078978601

IUPAC Name

2-hydroxy-N-phenylbenzene-1-carboximidic acid

Traditional Name

2-hydroxy-N-phenylbenzenecarboximidic acid

CAS Registry Number

Not Available

SMILES

OC(=NC1=CC=CC=C1)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C13H11NO2/c15-12-9-5-4-8-11(12)13(16)14-10-6-2-1-3-7-10/h1-9,15H,(H,14,16)

InChI Key

WKEDVNSFRWHDNR-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
Salicylic acid or derivatives
Salicylamide
Benzamide
Benzoic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

salicylanilides (CHEBI:239133 )
salicylamides (CHEBI:239133 )
benzanilide fungicide (CHEBI:239133 )

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	2.3	ALOGPS
logP	4.14	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.47	ChemAxon
pKa (Strongest Basic)	0.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.33 m³·mol⁻¹	ChemAxon
Polarizability	22.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	144.691	30932474
DeepCCS	[M-H]-	142.296	30932474
DeepCCS	[M-2H]-	176.481	30932474
DeepCCS	[M+Na]+	151.092	30932474
AllCCS	[M+H]+	147.9	32859911
AllCCS	[M+H-H2O]+	143.7	32859911
AllCCS	[M+NH4]+	151.8	32859911
AllCCS	[M+Na]+	152.9	32859911
AllCCS	[M-H]-	148.8	32859911
AllCCS	[M+Na-2H]-	148.6	32859911
AllCCS	[M+HCOO]-	148.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Salicylanilide	OC(=NC1=CC=CC=C1)C1=CC=CC=C1O	2870.8	Standard polar	33892256
Salicylanilide	OC(=NC1=CC=CC=C1)C1=CC=CC=C1O	2118.6	Standard non polar	33892256
Salicylanilide	OC(=NC1=CC=CC=C1)C1=CC=CC=C1O	1934.4	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 - Salicylanilide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9710000000-15e6a4470f2a4ab1de14	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicylanilide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicylanilide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicylanilide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicylanilide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicylanilide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicylanilide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicylanilide GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicylanilide 45V, Negative-QTOF	splash10-0006-9030000000-e48f6c30a6d293291772	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicylanilide 30V, Negative-QTOF	splash10-03di-2090000000-ec299da7ce3d24b2d812	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicylanilide 75V, Positive-QTOF	splash10-00dl-5900000000-b8aa3bf6d1afcb635542	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicylanilide 15V, Positive-QTOF	splash10-00dl-6900000000-b945dc044ce1f9fc2e60	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicylanilide 15V, Negative-QTOF	splash10-03di-0090000000-46d37a7c68caad25c8e3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicylanilide 60V, Negative-QTOF	splash10-0006-9000000000-d0c7077692156e0e386f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicylanilide 75V, Negative-QTOF	splash10-0006-9000000000-12cac967860306b55a9c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicylanilide 90V, Negative-QTOF	splash10-0006-9000000000-9cb450befba7cf016d2c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicylanilide 10V, Positive-QTOF	splash10-03di-3190000000-290ab36b4cb0b2b12988	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicylanilide 20V, Positive-QTOF	splash10-00di-5930000000-26634112b82a6cba391d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicylanilide 40V, Positive-QTOF	splash10-0006-9200000000-ee1ecd95d66c4b11a536	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicylanilide 10V, Negative-QTOF	splash10-03di-0190000000-4aa20f7b0785a65cbbbd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicylanilide 20V, Negative-QTOF	splash10-03dl-5890000000-095d39eee79cc87f6418	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicylanilide 40V, Negative-QTOF	splash10-0006-9200000000-a48e57a9819c03fe596c	2016-08-03	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

6610

KEGG Compound ID

C18915

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Salicylanilide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

239133

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 Salicylanilide (HMDB0257459)

MOL for HMDB0257459 (Salicylanilide)

3D MOL for HMDB0257459 (Salicylanilide)

3D SDF for HMDB0257459 (Salicylanilide)

3D-SDF for HMDB0257459 (Salicylanilide)

PDB for HMDB0257459 (Salicylanilide)

3D PDB for HMDB0257459 (Salicylanilide)

SMILES for HMDB0257459 (Salicylanilide)

INCHI for HMDB0257459 (Salicylanilide)

Structure for HMDB0257459 (Salicylanilide)

3D Structure for HMDB0257459 (Salicylanilide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra