MiMeDB: Showing metabocard for Salicylurate (MMDBc0033546)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:53:03 UTC

Update Date

2024-04-30 20:12:26 UTC

Metabolite ID

MMDBc0033546

Metabolite Identification

Common Name

Salicylurate

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 humans 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 ). Salicyluric acid has been found to be a microbial metabolite.

Structure

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


  Mrv1652305271900282D          

 14 14  0  0  0  0            999 V2000
 9998.7414 9999.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4557 9999.0793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.1715 9999.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8853 9999.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6011 9999.4919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.8853 9998.2550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.741410000.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.311910000.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0263 9999.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3119 9999.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5975 9999.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5974 9998.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3118 9997.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0263 9998.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  1  9  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033546

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CNC(=O)C1=C(O)C=CC=C1

> <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

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.1721

> <EXACT_MASS>
195.053157781

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.402480744498597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2-hydroxyphenyl)formamido]acetic acid

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.8719801626666666

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.195038343572135

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2728802708317217

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8536860417511458

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
48.098600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salicyluric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8664.3178665.718   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8665.6518664.948   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8666.9878665.718   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8668.3198664.948   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8669.6558665.718   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8668.3198663.409   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8664.3178667.258   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8661.6498667.258   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8662.9828664.948   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.6498665.718   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.3158664.948   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8660.3158663.408   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.6498662.638   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.9828663.408   0.000  0.00  0.00           C+0
CONECT    1    2    7    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1                                                            
CONECT    8   10                                                            
CONECT    9   10   14    1                                                  
CONECT   10    9   11    8                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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

Molecular Formula

C₉H₉NO₄

Average Mass

195.1721

Monoisotopic Mass

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=C(O)C=CC=C1

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.04 g/L	ALOGPS
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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0194143	Glycine N-acyltransferase	Enzyme	Q6IB77	Homo sapiens
MMDBp0194144	Glycine N-acyltransferase-like protein 1	Enzyme	Q969I3	Homo sapiens
MMDBp0194145	Glycine N-acyltransferase-like protein 2	Enzyme	Q8WU03	Homo sapiens
MMDBp0194146	Glycine N-acyltransferase-like protein 3	Enzyme	Q5SZD4	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	2219967
Human Urine	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 928	HMDB	12771321
Human Urine	Detected and Quantified	11		0.3	28	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12944546
Human Urine	Detected and Quantified	0.23		0.01	0.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12944546
Human Urine	Detected and Quantified	0.7		0.3	1.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12944546
Human Blood	Detected and Quantified	1	0.015			uM	Adult (>18 years old)	Both	Normal	HMDB	15315774
Human Urine	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 928	HMDB	17015248
Human Urine	Detected and Quantified	0.5				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22624806
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal cancer	HMDB	25037050
Human Urine	Detected and Quantified			0.59	0.87	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.61	0.87	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Bladder cancer	HMDB	28157703
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected and Quantified	0.5				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Urine	Detected and Quantified	0.23		0.01	0.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12944546
Human Urine	Detected and Quantified			0.59	0.87	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.61	0.87	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified	0.7		0.3	1.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12944546
Human Blood	Detected and Quantified	1.000	0.015			uM	Adult (>18 years old)	Both	Normal	HMDB	15315774
Human Urine	Detected and Quantified	11.0		0.3	28	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12944546
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	2219967
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22624806
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000840

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010505

KNApSAcK ID

Not Available

Chemspider ID

9835

KEGG Compound ID

C07588

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Salicyluric_acid

METLIN ID

617

PubChem Compound

10253

PDB ID

Not Available

ChEBI ID

9008

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Farid NA, Born GS, Kessler WV, Shaw SM, Lange WE: Improved colorimetric determination of salicylic acid and its metabolites in urine. Clin Chem. 1975 Jul;21(8):1167-8. [PubMed:1137922 ]
Kershaw RA, Mays DC, Bianchine JR, Gerber N: Disposition of aspirin and its metabolites in the semen of man. J Clin Pharmacol. 1987 Apr;27(4):304-9. doi: 10.1002/j.1552-4604.1987.tb03019.x. [PubMed:3680588 ]
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. doi: 10.1002/jps.2600700934. [PubMed: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. doi: 10.3109/03009748309102889. [PubMed:6857178 ]
Buskin JN, Upton RA, Williams RL: Improved liquid-chromatography of aspirin, salicylate, and salicyluric acid in plasma, with a modification for determining aspirin metabolites in urine. Clin Chem. 1982 May;28(5):1200-3. [PubMed:7074905 ]
Cham BE, Bochner F, Imhoff DM, Johns D, Rowland M: Simultaneous liquid-chromatographic quantitation of salicylic acid, salicyluric acid, and gentisic acid in urine. Clin Chem. 1980 Jan;26(1):111-4. [PubMed:7356541 ]
Sakurai M, Ohsako M, Nagano M, Nakamura C, Tsuzuki O, Ichikawa M, Matsumoto Y: [Effect of human serum albumin on transport of drugs through human erythrocyte membranes]. Yakugaku Zasshi. 1996 Aug;116(8):630-8. doi: 10.1248/yakushi1947.116.8_630. [PubMed:8831264 ]
Baxter GJ, Lawrence JR, Graham AB, Wiles D, Paterson JR: Identification and determination of salicylic acid and salicyluric acid in urine of people not taking salicylate drugs. Ann Clin Biochem. 2002 Jan;39(Pt 1):50-5. doi: 10.1258/0004563021901739. [PubMed:11853189 ]
Arancibia JA, Olivieri AC, Escandar GM: First- and second-order multivariate calibration applied to biological samples: determination of anti-inflammatories in serum and urine. Anal Bioanal Chem. 2002 Oct;374(3):451-9. doi: 10.1007/s00216-002-1466-9. Epub 2002 Sep 11. [PubMed:12373394 ]
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. doi: 10.1136/jcp.56.9.651. [PubMed:12944546 ]
Lares-Asseff I, Juarez-Olguin H, Flores-Perez J, Guille-Perez A, Vargas A: Pharmacokinetics and metabolic rates of acetyl salicylic acid and its metabolites in an Otomi ethnic group of Mexico. Biol Pharm Bull. 2004 May;27(5):706-9. doi: 10.1248/bpb.27.706. [PubMed:15133250 ]
Pirker R, Huck CW, Popp M, Bonn GK: Simultaneous determination of gentisic, salicyluric and salicylic acid in human plasma using solid-phase extraction, liquid chromatography and electrospray ionization mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Oct 5;809(2):257-64. doi: 10.1016/j.jchromb.2004.06.031. [PubMed:15315774 ]

Showing metabocard for Salicylurate (MMDBc0033546)

MOL for #<Metabolite:0x00007f9234045088>

3D MOL for #<Metabolite:0x00007f9234045088>

3D SDF for #<Metabolite:0x00007f9234045088>

3D-SDF for #<Metabolite:0x00007f9234045088>

PDB for #<Metabolite:0x00007f9234045088>

3D PDB for #<Metabolite:0x00007f9234045088>

SMILES for #<Metabolite:0x00007f9234045088>

INCHI for #<Metabolite:0x00007f9234045088>

Structure for #<Metabolite:0x00007f9234045088>

3D Structure for #<Metabolite:0x00007f9234045088>