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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:06:37 UTC

Update Date

2022-09-22 18:34:45 UTC

HMDB ID

HMDB0341275

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4'-Hydroxysalicylanilide

Description

osalmid, also known as oxaphenamide or driol, 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. osalmid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004221604152D          

 17 18  0  0  0  0            999 V2000
   -2.1434    2.0625    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
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    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
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  3  2  0  0  0  0
 12  4  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341275

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(NC(=O)C2=CC=CC=C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO3/c15-10-7-5-9(6-8-10)14-13(17)11-3-1-2-4-12(11)16/h1-8,15-16H,(H,14,17)

> <INCHI_KEY>
LGCMKPRGGJRYGM-UHFFFAOYSA-N

> <FORMULA>
C13H11NO3

> <MOLECULAR_WEIGHT>
229.235

> <EXACT_MASS>
229.073893218

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.492391917838077

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-N-(4-hydroxyphenyl)benzamide

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
2.457999978333333

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.45348690412438

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.91675775191049

> <JCHEM_PKA_STRONGEST_BASIC>
-4.207339130622262

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
65.55330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bilene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -6.668   8.470   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0     -12.003  11.550   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -8.002   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   11                                                       
CONECT    4    2   12                                                       
CONECT    5    7    9                                                       
CONECT    6    8    9                                                       
CONECT    7    5   10                                                       
CONECT    8    6   10                                                       
CONECT    9    5    6   14                                                  
CONECT   10    7    8   15                                                  
CONECT   11    3   12   13                                                  
CONECT   12    4   11   16                                                  
CONECT   13   11   14   17                                                  
CONECT   14    9   13                                                       
CONECT   15   10                                                            
CONECT   16   12                                                            
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Oxaphenamide	MeSH
Driol	MeSH
Fumispore	MeSH
4'-Hydroxysalicylanilide	MeSH
Osalmide	MeSH

Chemical Formula

C₁₃H₁₁NO₃

Average Molecular Weight

229.235

Monoisotopic Molecular Weight

229.073893218

IUPAC Name

2-hydroxy-N-(4-hydroxyphenyl)benzamide

Traditional Name

bilene

CAS Registry Number

Not Available

SMILES

OC1=CC=C(NC(=O)C2=CC=CC=C2O)C=C1

InChI Identifier

InChI=1S/C13H11NO3/c15-10-7-5-9(6-8-10)14-13(17)11-3-1-2-4-12(11)16/h1-8,15-16H,(H,14,17)

InChI Key

LGCMKPRGGJRYGM-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

Not Available

Ontology

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	2.15	ALOGPS
logP	2.46	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.92	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.55 m³·mol⁻¹	ChemAxon
Polarizability	23.49 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 Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxysalicylanilide 10V, Positive-QTOF	splash10-001i-0390000000-f23d62d170ebae025e99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxysalicylanilide 20V, Positive-QTOF	splash10-00di-1930000000-4826261a42fe08e3f768	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxysalicylanilide 40V, Positive-QTOF	splash10-0fkc-9400000000-99eff8adb4b24fd663c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxysalicylanilide 10V, Negative-QTOF	splash10-004i-0190000000-f03622a91fcb9c6cb5be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxysalicylanilide 20V, Negative-QTOF	splash10-004i-0790000000-222399134a27347637df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxysalicylanilide 40V, Negative-QTOF	splash10-0a4l-6900000000-20d30528b9dbb4507cfa	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

4602

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

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for 4'-Hydroxysalicylanilide (HMDB0341275)

MOL for HMDB0341275 (4'-Hydroxysalicylanilide)

3D MOL for HMDB0341275 (4'-Hydroxysalicylanilide)

3D SDF for HMDB0341275 (4'-Hydroxysalicylanilide)

3D-SDF for HMDB0341275 (4'-Hydroxysalicylanilide)

PDB for HMDB0341275 (4'-Hydroxysalicylanilide)

3D PDB for HMDB0341275 (4'-Hydroxysalicylanilide)

SMILES for HMDB0341275 (4'-Hydroxysalicylanilide)

INCHI for HMDB0341275 (4'-Hydroxysalicylanilide)

Structure for HMDB0341275 (4'-Hydroxysalicylanilide)

3D Structure for HMDB0341275 (4'-Hydroxysalicylanilide)

Predicted Kovats Retention Indices

MS/MS Spectra