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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2023-02-21 17:18:34 UTC

HMDB ID

HMDB0015687

Secondary Accession Numbers

HMDB15687

Metabolite Identification

Common Name

Salicylamide

Description

Salicylamide is the common name for the substance o-hydroxybenzamide, or amide of salicyl. Salicylamide is a non-prescription drug with analgesic and antipyretic properties. Its medicinal uses are similar to those of aspirin. Salicylamide is used in combination with both aspirin and caffeine in the over-the-counter pain remedies

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Carbamoylphenol	ChEBI
2-Carboxamidophenol	ChEBI
2-Hydroxybenzamide	ChEBI
O-Hydroxybenzamide	ChEBI
OHB	ChEBI
Salicilamida	ChEBI
Salicylamidum	ChEBI
Salicylic acid amide	ChEBI
Salicylate amide	Generator
Salicylamide sulfate	HMDB
Salicylamide, 3H-labeled	HMDB
Salicylamide, monosodium salt	HMDB
Salicylamide, calcium (2:1) salt	HMDB
Salicylamide sodium	HMDB

Chemical Formula

C₇H₇NO₂

Average Molecular Weight

137.136

Monoisotopic Molecular Weight

137.047678473

IUPAC Name

2-hydroxybenzamide

Traditional Name

salicylamide

CAS Registry Number

65-45-2

SMILES

NC(=O)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C7H7NO2/c8-7(10)5-3-1-2-4-6(5)9/h1-4,9H,(H2,8,10)

InChI Key

SKZKKFZAGNVIMN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:32114 )
salicylamides (CHEBI:32114 )
a small molecule (SALICYLAMIDE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Source

Exogenous

Exogenous (HMDB: HMDB0015687)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140 °C	Not Available
Boiling Point	181.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2060 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	1.280	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	121.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000807
[M+H]+	Not Available	124.7	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000807

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.82 g/L	ALOGPS
logP	0.74	ALOGPS
logP	1.17	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	8.21	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.12 m³·mol⁻¹	ChemAxon
Polarizability	13.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	128.056	31661259
DarkChem	[M-H]-	122.453	31661259
DeepCCS	[M+H]+	129.435	30932474
DeepCCS	[M-H]-	127.046	30932474
DeepCCS	[M-2H]-	162.997	30932474
DeepCCS	[M+Na]+	137.931	30932474
AllCCS	[M+H]+	129.0	32859911
AllCCS	[M+H-H2O]+	124.3	32859911
AllCCS	[M+NH4]+	133.4	32859911
AllCCS	[M+Na]+	134.6	32859911
AllCCS	[M-H]-	123.5	32859911
AllCCS	[M+Na-2H]-	125.1	32859911
AllCCS	[M+HCOO]-	126.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.27 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0089 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.78 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	78.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1160.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	345.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	105.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	215.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	88.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	292.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	337.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	318.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	733.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	270.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	901.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	495.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	288.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	189.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Salicylamide	NC(=O)C1=CC=CC=C1O	2336.9	Standard polar	33892256
Salicylamide	NC(=O)C1=CC=CC=C1O	1464.1	Standard non polar	33892256
Salicylamide	NC(=O)C1=CC=CC=C1O	1428.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Salicylamide,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC=C1C(N)=O	1551.9	Semi standard non polar	33892256
Salicylamide,1TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC=CC=C1O	1517.3	Semi standard non polar	33892256
Salicylamide,2TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=CC=C1O[Si](C)(C)C	1656.6	Semi standard non polar	33892256
Salicylamide,2TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=CC=C1O[Si](C)(C)C	1672.6	Standard non polar	33892256
Salicylamide,2TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=CC=C1O[Si](C)(C)C	1739.3	Standard polar	33892256
Salicylamide,2TMS,isomer #2	C[Si](C)(C)N(C(=O)C1=CC=CC=C1O)[Si](C)(C)C	1557.0	Semi standard non polar	33892256
Salicylamide,2TMS,isomer #2	C[Si](C)(C)N(C(=O)C1=CC=CC=C1O)[Si](C)(C)C	1666.0	Standard non polar	33892256
Salicylamide,2TMS,isomer #2	C[Si](C)(C)N(C(=O)C1=CC=CC=C1O)[Si](C)(C)C	1885.1	Standard polar	33892256
Salicylamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC=C1C(=O)N([Si](C)(C)C)[Si](C)(C)C	1680.6	Semi standard non polar	33892256
Salicylamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC=C1C(=O)N([Si](C)(C)C)[Si](C)(C)C	1706.8	Standard non polar	33892256
Salicylamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC=C1C(=O)N([Si](C)(C)C)[Si](C)(C)C	1730.0	Standard polar	33892256
Salicylamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(N)=O	1791.6	Semi standard non polar	33892256
Salicylamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=CC=C1O	1765.2	Semi standard non polar	33892256
Salicylamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	2104.4	Semi standard non polar	33892256
Salicylamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	2093.2	Standard non polar	33892256
Salicylamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	2052.7	Standard polar	33892256
Salicylamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=CC=C1O)[Si](C)(C)C(C)(C)C	2044.0	Semi standard non polar	33892256
Salicylamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=CC=C1O)[Si](C)(C)C(C)(C)C	2050.3	Standard non polar	33892256
Salicylamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=CC=C1O)[Si](C)(C)C(C)(C)C	2077.8	Standard polar	33892256
Salicylamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2341.8	Semi standard non polar	33892256
Salicylamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2328.1	Standard non polar	33892256
Salicylamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2120.3	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08797	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08797	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08797

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4963

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Salicylamide

METLIN ID

Not Available

PubChem Compound

5147

PDB ID

Not Available

ChEBI ID

32114

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1281501

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Showing metabocard for Salicylamide (HMDB0015687)

MOL for HMDB0015687 (Salicylamide)

3D MOL for HMDB0015687 (Salicylamide)

3D SDF for HMDB0015687 (Salicylamide)

3D-SDF for HMDB0015687 (Salicylamide)

PDB for HMDB0015687 (Salicylamide)

3D PDB for HMDB0015687 (Salicylamide)

SMILES for HMDB0015687 (Salicylamide)

INCHI for HMDB0015687 (Salicylamide)

Structure for HMDB0015687 (Salicylamide)

3D Structure for HMDB0015687 (Salicylamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized