Showing Compound 3-mercaptopyruvate (FDB030434)

Record Information

Version

1.0

Creation date

2015-05-07 19:14:46 UTC

Update date

2019-11-26 03:21:44 UTC

Primary ID

FDB030434

Secondary Accession Numbers

FDB021862

Chemical Information

FooDB Name

3-mercaptopyruvate

Description

3-mercaptopyruvic acid, also known as beta-mercaptopyruvate or beta-thiopyruvic acid, belongs to alpha-keto acids and derivatives class of compounds. Those are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. 3-mercaptopyruvic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 3-mercaptopyruvic acid can be found in a number of food items such as garland chrysanthemum, rubus (blackberry, raspberry), tarragon, and arrowhead, which makes 3-mercaptopyruvic acid a potential biomarker for the consumption of these food products. 3-mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. In humans, 3-mercaptopyruvic acid is involved in a couple of metabolic pathways, which include cysteine metabolism and cystinosis, ocular nonnephropathic. 3-mercaptopyruvic acid is also involved in beta-mercaptolactate-cysteine disulfiduria, which is a metabolic disorder. 3-Mercaptopyruvic acid is an intermediate in cysteine metabolism. It has been studied as a potential treatment for cyanide poisoning, but its half-life is too short for it to be clinically effective. Instead, prodrugs, such as sulfanegen, are being evaluated to compensate for the short half-life of 3-mercaptopyruvic acid .

CAS Number

2464-23-5

Structure

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

Synonyms

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

Showing 1 to 10 of 15 entries

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

Disposition

Route of exposure:

Enteral:

Ingestion

Animal

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

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

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 3-mercaptopyruvate (FDB030434)

Structure for FDB030434 (3-mercaptopyruvate)