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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:13 UTC

HMDB ID

HMDB0000840

Secondary Accession Numbers

HMDB00840

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 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>
HMDB0000840

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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=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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15315774)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)
Feces (PMID: 27543620)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000840)

Source

Endogenous

Endogenous (HMDB: HMDB0000840)

Animal

Animal (HMDB: HMDB0000840)

Microbe

Microbe (HMDB: HMDB0000840)

Exogenous

Food

Food (HMDB: HMDB0000840)
Legumes (HMDB: HMDB0000840)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0000840)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0000840)

Tea

Tea products (HMDB: HMDB0000840)

Fat and oil

Olive oil (HMDB: HMDB0000840)

Fruit

Fruits (HMDB: HMDB0000840)

Vegetable

Vegetables (HMDB: HMDB0000840)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0000840)

Nut

Nuts (HMDB: HMDB0000840)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0000840)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Milk and milk products (FooDB: FOOD00863)

Exogenous (HMDB: HMDB0000840)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	168 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	0.95	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	133.01	30932474
[M-H]-	Not Available	135.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000294

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.778	31661259
DarkChem	[M-H]-	136.857	31661259
AllCCS	[M+H]+	141.994	32859911
AllCCS	[M-H]-	140.068	32859911
DeepCCS	[M+H]+	139.538	30932474
DeepCCS	[M-H]-	137.143	30932474
DeepCCS	[M-2H]-	172.018	30932474
DeepCCS	[M+Na]+	146.505	30932474
AllCCS	[M+H]+	142.0	32859911
AllCCS	[M+H-H2O]+	137.9	32859911
AllCCS	[M+NH4]+	145.8	32859911
AllCCS	[M+Na]+	146.9	32859911
AllCCS	[M-H]-	140.1	32859911
AllCCS	[M+Na-2H]-	140.7	32859911
AllCCS	[M+HCOO]-	141.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Salicyluric acid	OC(=O)CNC(=O)C1=C(O)C=CC=C1	2997.0	Standard polar	33892256
Salicyluric acid	OC(=O)CNC(=O)C1=C(O)C=CC=C1	1848.4	Standard non polar	33892256
Salicyluric acid	OC(=O)CNC(=O)C1=C(O)C=CC=C1	1931.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Salicyluric acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C1=CC=CC=C1O	1958.6	Semi standard non polar	33892256
Salicyluric acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC=C1C(=O)NCC(=O)O	1993.1	Semi standard non polar	33892256
Salicyluric acid,1TMS,isomer #3	C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CC=C1O	1933.4	Semi standard non polar	33892256
Salicyluric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C1=CC=CC=C1O[Si](C)(C)C	2085.3	Semi standard non polar	33892256
Salicyluric acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1O)[Si](C)(C)C	1926.0	Semi standard non polar	33892256
Salicyluric acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC=CC=C1C(=O)N(CC(=O)O)[Si](C)(C)C	2002.8	Semi standard non polar	33892256
Salicyluric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1O[Si](C)(C)C)[Si](C)(C)C	2016.3	Semi standard non polar	33892256
Salicyluric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1O[Si](C)(C)C)[Si](C)(C)C	2007.6	Standard non polar	33892256
Salicyluric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1O[Si](C)(C)C)[Si](C)(C)C	2151.2	Standard polar	33892256
Salicyluric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=CC=C1O	2204.0	Semi standard non polar	33892256
Salicyluric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)NCC(=O)O	2245.1	Semi standard non polar	33892256
Salicyluric acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CC=C1O	2175.6	Semi standard non polar	33892256
Salicyluric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	2547.3	Semi standard non polar	33892256
Salicyluric acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1O)[Si](C)(C)C(C)(C)C	2417.7	Semi standard non polar	33892256
Salicyluric acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	2489.8	Semi standard non polar	33892256
Salicyluric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2685.1	Semi standard non polar	33892256
Salicyluric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2615.7	Standard non polar	33892256
Salicyluric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2530.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Salicyluric acid GC-MS (3 TMS)	splash10-0006-1921000000-494271209c45ba6e054e	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Salicyluric acid GC-MS (2 TMS)	splash10-0a4l-3942000000-04aa13977839f7430e87	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Salicyluric acid GC-MS (Non-derivatized)	splash10-0006-1921000000-494271209c45ba6e054e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Salicyluric acid GC-MS (Non-derivatized)	splash10-0a4l-3942000000-04aa13977839f7430e87	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Salicyluric acid GC-EI-TOF (Non-derivatized)	splash10-0006-0921000000-3ee04ebbc6ba044f6e25	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Salicyluric acid GC-EI-TOF (Non-derivatized)	splash10-0a4l-1942000000-14e4da43f05418868f3d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2900000000-558ece7e40b6a2505e9b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-7972000000-6d3342d12b15e7739ff0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salicyluric acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-0900000000-5fc858fcdd858768270f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00di-3900000000-05f9fa1a8cebedcf52c9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-01bc-9200000000-169ad1809ba2a4accf08	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0006-0900000000-d6d7f1809f1779d278b3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0udi-2900000000-d099d157b6253af681d3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0006-9100000000-96900edd4f6aa1f2c3b9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0006-9000000000-511684503214f5c46668	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0006-9000000000-8daa85624d5a46018858	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-QQ , negative-QTOF	splash10-0006-0900000000-d6d7f1809f1779d278b3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-QQ , negative-QTOF	splash10-0udi-2900000000-d099d157b6253af681d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-QQ , negative-QTOF	splash10-0006-9100000000-96900edd4f6aa1f2c3b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-QQ , negative-QTOF	splash10-0006-9000000000-511684503214f5c46668	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-QQ , negative-QTOF	splash10-0006-9000000000-8daa85624d5a46018858	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid LC-ESI-IT , negative-QTOF	splash10-0udi-0900000000-7f8ca4379a27c9d6fad9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid 10V, Negative-QTOF	splash10-0udi-1900000000-9b88237d9c8a1f5864a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid 40V, Negative-QTOF	splash10-0006-9000000000-5f0973db56ba7f4637a5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid 20V, Negative-QTOF	splash10-0006-9100000000-8d96e93a2efb83a5b59b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid 30V, Negative-QTOF	splash10-0006-9000000000-b7f5fb721797c7880142	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Salicyluric acid 40V, Negative-QTOF	splash10-0006-9000000000-e41d3042048b1bf5a637	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicyluric acid 10V, Positive-QTOF	splash10-0002-2900000000-329e9ccbe80298c87ec2	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicyluric acid 20V, Positive-QTOF	splash10-0fk9-5900000000-be142fe17e5fc055f83c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicyluric acid 40V, Positive-QTOF	splash10-00fu-9200000000-1490fe4359681e391fd3	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicyluric acid 10V, Negative-QTOF	splash10-0006-0900000000-47cf95d67574e923d000	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicyluric acid 20V, Negative-QTOF	splash10-0f6x-3900000000-65d91bbe9e076cff4177	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salicyluric acid 40V, Negative-QTOF	splash10-006x-9100000000-e75a3b91d96f8d45614e	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

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	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	1.000 +/- 0.015 uM	Adult (>18 years old)	Both	Normal	15315774	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.59-0.87 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	0.7 (0.3-1.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12944546	details
Urine	Detected and Quantified	0.5 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected and Quantified	0.23 (0.01-0.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12944546	details
Urine	Detected and Quantified	11.0 (0.3-28) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12944546	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22624806	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 928	12771321	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 928	17015248	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.61-0.87 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	2219967	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

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

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

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. [PubMed:8831264 ]
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. [PubMed:15315774 ]
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. [PubMed:15133250 ]
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. [PubMed:3680588 ]
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. [PubMed:12944546 ]
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. Epub 2002 Sep 11. [PubMed:12373394 ]
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. [PubMed:11853189 ]
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. [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. [PubMed:6857178 ]

Enzymes

Enzyme Details

1. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Reactions

Salicylic acid → Salicyluric acid	details

Enzyme Details

2. Glycine N-acyltransferase-like protein 1

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:: GLYATL1
Uniprot ID:: Q969I3
Molecular weight:: 35100.895

Enzyme Details

3. Glycine N-acyltransferase-like protein 2

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:: GLYATL2
Uniprot ID:: Q8WU03
Molecular weight:: 34277.055

Enzyme Details

4. Glycine N-acyltransferase-like protein 3

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:: GLYATL3
Uniprot ID:: Q5SZD4
Molecular weight:: 32703.3

Showing metabocard for Salicyluric acid (HMDB0000840)

MOL for HMDB0000840 (Salicyluric acid)

3D MOL for HMDB0000840 (Salicyluric acid)

3D SDF for HMDB0000840 (Salicyluric acid)

3D-SDF for HMDB0000840 (Salicyluric acid)

PDB for HMDB0000840 (Salicyluric acid)

3D PDB for HMDB0000840 (Salicyluric acid)

SMILES for HMDB0000840 (Salicyluric acid)

INCHI for HMDB0000840 (Salicyluric acid)

Structure for HMDB0000840 (Salicyluric acid)

3D Structure for HMDB0000840 (Salicyluric acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions