Milk Composition Database: Showing metabocard for Salicyluric acid (BMDB0000840)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:37:22 UTC

Update Date

2020-04-22 15:05:34 UTC

MCDB ID

BMDB0000840

Secondary Accession Numbers

BMDB00840

Metabolite Identification

Common Name

Salicyluric acid

Description

Salicylurate, also known as salicyloylglycine or O-hydroxyhippate, 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. Salicylurate exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Salicylurate exists in all eukaryotes, ranging from yeast to humans.

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=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 )

Physical Properties

State

Solid

Experimental 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)

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0006-1921000000-494271209c45ba6e054e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4l-3942000000-04aa13977839f7430e87	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-1921000000-494271209c45ba6e054e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4l-3942000000-04aa13977839f7430e87	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0921000000-3ee04ebbc6ba044f6e25	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4l-1942000000-14e4da43f05418868f3d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2900000000-558ece7e40b6a2505e9b	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-7972000000-6d3342d12b15e7739ff0	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-5fc858fcdd858768270f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-3900000000-05f9fa1a8cebedcf52c9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01bc-9200000000-169ad1809ba2a4accf08	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-d6d7f1809f1779d278b3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-2900000000-d099d157b6253af681d3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9100000000-96900edd4f6aa1f2c3b9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-511684503214f5c46668	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-8daa85624d5a46018858	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-d6d7f1809f1779d278b3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-2900000000-d099d157b6253af681d3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9100000000-96900edd4f6aa1f2c3b9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-511684503214f5c46668	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-8daa85624d5a46018858	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-0900000000-7f8ca4379a27c9d6fad9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1900000000-9b88237d9c8a1f5864a8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-5f0973db56ba7f4637a5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9100000000-8d96e93a2efb83a5b59b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-9000000000-b7f5fb721797c7880142	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e41d3042048b1bf5a637	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-2900000000-329e9ccbe80298c87ec2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-5900000000-be142fe17e5fc055f83c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fu-9200000000-1490fe4359681e391fd3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-47cf95d67574e923d000	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6x-3900000000-65d91bbe9e076cff4177	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9100000000-e75a3b91d96f8d45614e	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable	PMID: 23438684	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable	PMID: 28306241	details
Detected but not Quantified	Not Applicable	PMID: 29291809	details

External Links

HMDB ID

HMDB0000840

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.

Showing metabocard for Salicyluric acid (BMDB0000840)

Structure for BMDB0000840 (Salicyluric acid)