Livestock Metabolome Database: Showing metabocard for Salicyluric acid (LMDB00258)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:51 UTC

Update Date

2016-09-23 18:45:02 UTC

Lmdb

LMDB00258

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Salicyluric acid

Description

Salicyluric acid is an aryl glycine conjugate formed by the body to eliminate excess salicylates, including aspirin. Aspirin is rapidly hydrolysed to salicylic acid which is further metabolized to various compounds, including salicyluric acid (SU) as well as various acyl and phenolic glucuronides, and hydroxylated metabolites. SU is the major metabolite of SA excreted in urine and it is present in the urine of people who have not taken salicylate drugs, although it has no anti-inflammatory effects in animals or in animals. More salicyluric acid (SU) is excreted in the urine of vegetarians than in non-vegetarians, primarily because fruits and vegetables are important sources of dietary salicylates. However, significantly less (10-15X) SU is excreted by vegetarians than individuals taking low-dose aspirin (PMID: 12944546 ). The induction of the salicyluric acid formation is one of the saturable pathways of salicylate elimination. The formation of the methyl ester of salicyluric acid is observed during the quantitation of salicyluric acid and other salicylate metabolites in urine by high-pressure liquid chromatography. This methyl ester formation causes artificially low values for salicyluric acid and high values for salicylic acid. (PMID: 6101164 , 6857178 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(2-Hydroxybenzoyl)-glycine	ChEBI
N-Salicyloylglycine	ChEBI
O-Hydroxyhippuric acid	ChEBI
Salicyloylglycine	ChEBI
Salicylurate	ChEBI
O-Hydroxyhippate	Generator
O-Hydroxyhippic acid	Generator
Salicylate	Generator
Salicylic acid	Generator
((2-Hydroxybenzoyl)amino)acetic acid	HMDB
(2-Hydroxybenzoyl)glycine	HMDB
2-Hydroxybenzoylaminoacetate	HMDB
2-Hydroxybenzoylaminoacetic acid	HMDB
2-Hydroxybenzoylglycine	HMDB
2-Hydroxyhippurate	HMDB
2-Hydroxyhippuric acid	HMDB
N-O-Hydroxybenzoylglycine	HMDB
O-Hydroxy-hippurate	HMDB
O-Hydroxy-hippuric acid	HMDB
O-Hydroxyhippurate	HMDB
Ortho-hydroxyhippurate	HMDB
Ortho-hydroxyhippuric acid	HMDB
Salicylglycine	HMDB
[(2-Hydroxybenzoyl)amino]acetate	HMDB
[(2-Hydroxybenzoyl)amino]acetic acid	HMDB
Salicylurate, monosodium salt	HMDB
N-(O-Hydroxybenzoyl)glycine	HMDB
2-[(2-Hydroxybenzoyl)amino]acetic acid	HMDB
2'-Hydroxyhippuric acid	HMDB

Chemical Formula

C₉H₉NO₄

Average Molecular Weight

195.1721

Monoisotopic Molecular Weight

195.053157781

IUPAC Name

2-[(2-hydroxyphenyl)formamido]acetic acid

Traditional Name

salicyluric acid

CAS Registry Number

487-54-7

SMILES

OC(=O)CNC(=O)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C9H9NO4/c11-7-4-2-1-3-6(7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)

InChI Key

ONJSZLXSECQROL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hippuric acids

Alternative Parents

Substituents

Hippuric acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Salicylic acid or derivatives
Salicylamide
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acyl-amino acid (CHEBI:9008 )
N-acylglycine (CHEBI:9008 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	0.51	ALOGPS
logP	0.87	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.27	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.1 m³·mol⁻¹	ChemAxon
Polarizability	18.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0006-1921000000-494271209c45ba6e054e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4l-3942000000-04aa13977839f7430e87	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-1921000000-494271209c45ba6e054e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4l-3942000000-04aa13977839f7430e87	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0921000000-3ee04ebbc6ba044f6e25	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4l-1942000000-14e4da43f05418868f3d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2900000000-558ece7e40b6a2505e9b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-7972000000-6d3342d12b15e7739ff0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-5fc858fcdd858768270f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-3900000000-05f9fa1a8cebedcf52c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01bc-9200000000-169ad1809ba2a4accf08	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-d6d7f1809f1779d278b3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-2900000000-d099d157b6253af681d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9100000000-96900edd4f6aa1f2c3b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-511684503214f5c46668	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-8daa85624d5a46018858	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-d6d7f1809f1779d278b3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-2900000000-d099d157b6253af681d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9100000000-96900edd4f6aa1f2c3b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-511684503214f5c46668	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-8daa85624d5a46018858	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-0900000000-7f8ca4379a27c9d6fad9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1900000000-9b88237d9c8a1f5864a8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-5f0973db56ba7f4637a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9100000000-8d96e93a2efb83a5b59b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-9000000000-b7f5fb721797c7880142	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e41d3042048b1bf5a637	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-2900000000-329e9ccbe80298c87ec2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-5900000000-be142fe17e5fc055f83c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fu-9200000000-1490fe4359681e391fd3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-47cf95d67574e923d000	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6x-3900000000-65d91bbe9e076cff4177	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9100000000-e75a3b91d96f8d45614e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000840

FooDB ID

FDB010505

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

617

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lawrence JR, Peter R, Baxter GJ, Robson J, Graham AB, Paterson JR: Urinary excretion of salicyluric and salicylic acids by non-vegetarians, vegetarians, and patients taking low dose aspirin. J Clin Pathol. 2003 Sep;56(9):651-3. [12944546 ]
Day RO, Dromgoole SH, Furst DE, Hignite C, Paulus HE: Formation of methyl ester of salicyluric acid during quantitation of salicyluric acid in urine by high-pressure liquid chromatography. J Pharm Sci. 1981 Sep;70(9):1090-2. [6101164 ]
Olsson B: Decreasing serum salicylate concentrations during long-term administration of acetylsalicylic acid in healthy volunteers. Discussion of possible clinical implications. Scand J Rheumatol. 1983;12(2):81-4. [6857178 ]

Showing metabocard for Salicyluric acid (LMDB00258)

Structure for LMDB00258 (Salicyluric acid)