ECMDB: 3-Mercaptopyruvic acid (ECMDB01368) (M2MDB000358)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (985)

Record Information

Version

2.0

Creation Date

2012-05-31 13:51:01 -0600

Update Date

2015-09-13 12:56:11 -0600

Secondary Accession Numbers

ECMDB01368

Identification

Name:

3-Mercaptopyruvic acid

Description

3-Mercaptopyruvic acid is an intermediate in the metabolism of Cysteine and the production of hydrogen sulfide. It is a substrate for3-mercaptopyruvate sulfurtransferase which catalyzes the following reaction: H+ + 3-Mercaptopyruvic acid <=> Pyruvic acid + Hydrogen sulfide.

Structure

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

Synonyms:

β-mercaptopyruvate
β-mercaptopyruvic acid
β-thiopyruvate
β-thiopyruvic acid
3-Mercapto-pyruvate
3-Mercapto-pyruvic acid
3-Mercaptopyruvate
3-Mercaptopyruvic acid
b-3-mercapto-2-oxo-Propanoate
b-3-mercapto-2-oxo-Propanoic acid
b-Mercaptopyruvate
b-Mercaptopyruvic acid
b-Thiopyruvate
b-Thiopyruvic acid
Beta-3-Mercapto-2-oxo-propanoate
Beta-3-Mercapto-2-oxo-propanoic acid
Beta-Mercaptopyruvate
Beta-Mercaptopyruvic acid
Beta-Thiopyruvate
Beta-Thiopyruvic acid
Mercaptopyruvate
Mercaptopyruvic acid
MercPyr
Thiopyruvate
Thiopyruvic acid
β-3-mercapto-2-oxo-Propanoate
β-3-mercapto-2-oxo-Propanoic acid
β-Mercaptopyruvate
β-Mercaptopyruvic acid
β-Thiopyruvate
β-Thiopyruvic acid

Chemical Formula:

C₃H₄O₃S

Weight:

Average: 120.127
Monoisotopic: 119.988114684

InChI Key:

OJOLFAIGOXZBCI-UHFFFAOYSA-N

InChI:

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

CAS number:

2464-23-5

IUPAC Name:

2-oxo-3-sulfanylpropanoic acid

Traditional IUPAC Name:

β-mercaptopyruvic acid

SMILES:

OC(=O)C(=O)CS

Chemical Taxonomy

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 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Hydrogen Sulfide Biosynthesis I

PW002066

KEGG Pathways:

Cysteine and methionine metabolism ec00270
Metabolic pathways eco01100

EcoCyc Pathways:

hydrogen sulfide biosynthesis PWY0-1534

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9000000000-b81f8808977132c3a8ac	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9300000000-5100fd5cbb3bf9df1e75	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-003r-9200000000-f1e0c53958ad51dc0068	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-001j-9000000000-60f6deb41f42078dd60c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-001i-9000000000-5dc69d3b59bd15290aef	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-02t9-9000000000-e1511333b005fa911312	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-9000000000-65854057c742d34c8dbb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-006w-9000000000-66939f30bca1061b4b83	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-2900000000-0da521157f8235fe7758	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-7900000000-8c127be0565b54938cd2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9000000000-d4a8d07d451ba309b2e2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-849e74ceb9308736ba6d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gb9-2900000000-5a713232367a68a966a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fk9-9300000000-564344466a63b943c6da	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-9200000000-95772f7f626a811df489	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-32551e3b5faf0b1e7000	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-572c315b879edca344fa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9400000000-8738d67598547a4b3429	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-4ba1ab7a6a1dc95bba23	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-6a9a04efc4b7bb2af1eb	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	16208
HMDB ID	HMDB01368
Pubchem Compound ID	98
Kegg ID	C00957
ChemSpider ID	96
Wikipedia ID	3-Mercaptopyruvic_acid
BioCyc ID	3-MERCAPTO-PYRUVATE
EcoCyc ID	3-MERCAPTO-PYRUVATE

Enzymes

Protein Details

1. Aspartate aminotransferase

General function:: Involved in transferase activity
Specific function:: L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate
Gene Name:: aspC
Uniprot ID:: P00509
Molecular weight:: 43573

Reactions

L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate.

Protein Details

2. 3-mercaptopyruvate sulfurtransferase

General function:: Involved in thiosulfate sulfurtransferase activity
Specific function:: Transfers a sulfur ion to cyanide or to other thiol compounds. Also has weak rhodanese activity (130-fold lower). Its participation in detoxification of cyanide may be small. May be involved in the enhancement of serine sensitivity
Gene Name:: sseA
Uniprot ID:: P31142
Molecular weight:: 30812

Reactions

3-mercaptopyruvate + cyanide = pyruvate + thiocyanate.

Protein Details

3. Thiosulfate sulfurtransferase YnjE

General function:: Involved in thiosulfate sulfurtransferase activity
Specific function:: Thiosulfate + cyanide = sulfite + thiocyanate
Gene Name:: ynjE
Uniprot ID:: P78067
Molecular weight:: 48228

Reactions

Thiosulfate + cyanide = sulfite + thiocyanate.

3-Mercaptopyruvic acid (ECMDB01368) (M2MDB000358)

Structure for #<Compound:0xab734f50>

Enzymes

Reactions

Reactions

Reactions