Showing Compound 3-Mercapto-2-oxopropanoic acid (FDB021862)

Record Information

Version

1.0

Creation date

2011-06-15 17:54:18 UTC

Update date

2020-04-21 18:02:15 UTC

Primary ID

FDB021862

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Mercapto-2-oxopropanoic acid

Description

3-Mercaptopyruvic acid, also known as beta-thiopyruvate or 3-mercapto-2-oxopropanoate, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. 3-Mercaptopyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. 3-Mercaptopyruvic acid has been detected, but not quantified in, several different foods, such as half-highbush blueberries, bitter gourds, new zealand spinachs, horseradish tree, and red huckleberries. This could make 3-mercaptopyruvic acid a potential biomarker for the consumption of these foods.

CAS Number

2464-23-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
3-Mercapto-2-oxopropanoic acid	ChEBI
3-Mercaptopyruvate	ChEBI
Mercaptopyruvate	ChEBI
3-Mercapto-2-oxopropanoate	Generator
Mercaptopyruvic acid	Generator
3-Mercapto-pyruvate	HMDB
3-Mercapto-pyruvic acid	HMDB
beta-3-Mercapto-2-oxo-propanoate	HMDB
beta-3-Mercapto-2-oxo-propanoic acid	HMDB
beta-Mercaptopyruvate	HMDB
beta-Mercaptopyruvic acid	HMDB
beta-Thiopyruvate	HMDB
beta-Thiopyruvic acid	HMDB
Thiopyruvate	HMDB
3-Mercaptopyruvate monosodium salt	HMDB
3-Mercaptopyruvic acid	ChEBI
b-Mercaptopyruvic acid	db_source

Predicted Properties

Property	Value	Source
Water Solubility	9.09 g/L	ALOGPS
logP	0.15	ALOGPS
logP	0.29	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-9.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.82 m³·mol⁻¹	ChemAxon
Polarizability	10.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C3H4O3S

IUPAC name

2-oxo-3-sulfanylpropanoic acid

InChI Identifier

InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)

InChI Key

OJOLFAIGOXZBCI-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C(=O)CS

Average Molecular Weight

120.127

Monoisotopic Molecular Weight

119.988114684

Classification

Description

Belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Alpha-keto acids and derivatives

Direct Parent

Alpha-keto acids and derivatives

Alternative Parents

Substituents

Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alkylthiol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

thiol (CHEBI:16208 )
2-oxo monocarboxylic acid (CHEBI:16208 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Cryst. (Me2CO/petrol)	CCD
Mass Composition	C 30.00%; H 3.36%; O 39.96%; S 26.69%	CCD
Melting Point	Mp 140-141°	CCD
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	3-Mercapto-2-oxopropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9000000000-b81f8808977132c3a8ac	Spectrum
Predicted GC-MS	3-Mercapto-2-oxopropanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9300000000-5100fd5cbb3bf9df1e75	Spectrum
Predicted GC-MS	3-Mercapto-2-oxopropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Mercapto-2-oxopropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-003r-9200000000-f1e0c53958ad51dc0068	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-001j-9000000000-60f6deb41f42078dd60c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-001i-9000000000-5dc69d3b59bd15290aef	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-02t9-9000000000-e1511333b005fa911312	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-9000000000-65854057c742d34c8dbb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-006w-9000000000-66939f30bca1061b4b83	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-2900000000-0da521157f8235fe7758	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-7900000000-8c127be0565b54938cd2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9000000000-d4a8d07d451ba309b2e2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-849e74ceb9308736ba6d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gb9-2900000000-5a713232367a68a966a0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fk9-9300000000-564344466a63b943c6da	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-9200000000-95772f7f626a811df489	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-32551e3b5faf0b1e7000	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-572c315b879edca344fa	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9400000000-8738d67598547a4b3429	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-4ba1ab7a6a1dc95bba23	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-6a9a04efc4b7bb2af1eb	2021-09-25	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

Not Available

KEGG Compound ID

C00957

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16208

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01368

CRC / DFC (Dictionary of Food Compounds) ID

NRC89-Q:NRC89-Q

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

36476

KNApSAcK ID

C00007464

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

3-Mercaptopyruvic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Aspartate aminotransferase, cytoplasmic	GOT1	P17174
Aspartate aminotransferase, mitochondrial	GOT2	P00505
3-mercaptopyruvate sulfurtransferase	MPST	P25325
Cystathionine gamma-lyase	CTH	P32929