ECMDB: 3-Sulfopyruvic acid (ECMDB21002) (M2MDB001422)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)Transporters (1)XML

Proteins (804)

Record Information

Version

2.0

Creation Date

2012-05-31 14:54:00 -0600

Update Date

2015-06-03 17:20:24 -0600

Secondary Accession Numbers

ECMDB21002

Identification

Name:

3-Sulfopyruvic acid

Description

3-Sulfopyruvic acid is the product of the transamination of cysteinesulfonate in a reaction catalyzed by aspartate aminotransferase. 3-sulfopyruvic acid is stable and is reduced by malate dehydrogenase to beta-sulfolactate. Cysteinesulfonate, 3-sulfopyruvic acid, and beta-sulfolactate are reversibly interconverted in vivo. (PMID: 3346220)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Carboxy-2-oxoethanesulfonate
2-Carboxy-2-oxoethanesulfonic acid
2-Carboxy-2-oxoethanesulphonate
2-Carboxy-2-oxoethanesulphonic acid
2-Oxo-3-sulfo-Propanoate
2-Oxo-3-sulfo-Propanoic acid
2-Oxo-3-sulfopropanoate
2-Oxo-3-sulfopropanoic acid
2-Oxo-3-sulpho-Propanoate
2-Oxo-3-sulpho-Propanoic acid
2-Oxo-3-sulphopropanoate
2-Oxo-3-sulphopropanoic acid
3-Sulfopyruvate
3-Sulfopyruvic acid
3-Sulphopyruvate
3-Sulphopyruvic acid
b-Sulfopyruvate
b-Sulfopyruvic acid
b-Sulphopyruvate
b-Sulphopyruvic acid
Beta-Sulfopyruvate
Beta-Sulfopyruvic acid
Beta-Sulphopyruvate
Beta-Sulphopyruvic acid
Sulfopyruvate
Sulfopyruvic acid
Sulphopyruvate
Sulphopyruvic acid
β-Sulfopyruvate
β-Sulfopyruvic acid
β-Sulphopyruvate
β-Sulphopyruvic acid

Chemical Formula:

C₃H₄O₆S

Weight:

Average: 168.125
Monoisotopic: 167.97285855

InChI Key:

BUTHMSUEBYPMKJ-UHFFFAOYSA-N

InChI:

InChI=1S/C3H4O6S/c4-2(3(5)6)1-10(7,8)9/h1H2,(H,5,6)(H,7,8,9)

CAS number:

98022-26-5

IUPAC Name:

2-oxo-3-sulfopropanoic acid

Traditional IUPAC Name:

sulfopyruvate

SMILES:

OC(=O)C(=O)CS(O)(=O)=O

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
Alkanesulfonic acid
Sulfonyl
Organosulfonic acid
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxyalkanesulfonic acid (CHEBI:16894 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-1.701	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	12.9 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-0.74	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	-1.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.74 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.33 m³·mol⁻¹	ChemAxon
Polarizability	12.46 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:

Cysteic acid + alpha-Ketoglutarate <> 3-Sulfopyruvic acid + L-Glutamate
Cysteic acid + Oxoglutaric acid <> L-Glutamate + 3-Sulfopyruvic acid

SMPDB Pathways:

Collection of Reactions without pathways

PW001891

KEGG Pathways:

Cysteine and methionine metabolism ec00270
Methane metabolism ec00680
Microbial metabolism in diverse environments ec01120

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9300000000-8fb65d208d027ce47187	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9310000000-852dd197381758581de3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-094511841526eb040890	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0g4i-2900000000-77b615b663328d3fe524	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9500000000-bf672301532b1817de74	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-4e67b7b2992779903679	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-3900000000-9801b0e1faeb0f73a93b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-7900000000-7a1af7df664000361846	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-5900000000-8c6e190717a212c1f83b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-762dfd631fed0cc2e666	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-9000000000-440cd593424b9672a3c7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-62e3604ba5cc3505465b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-9600000000-fad73b53a872db46f577	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ff8f9426210041ec9988	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C 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
Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. Pubmed: 23455439
Weinstein, C. L., Griffith, O. W. (1988). "Cysteinesulfonate and beta-sulfopyruvate metabolism. Partitioning between decarboxylation, transamination, and reduction pathways." J Biol Chem 263:3735-3743. Pubmed: 3346220

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16894
HMDB ID	HMDB04045
Pubchem Compound ID	440717
Kegg ID	C05528
ChemSpider ID	389590
Wikipedia ID	Not Available
BioCyc ID	Not Available
Ligand Expo	SPV

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. Malate dehydrogenase

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Catalyzes the reversible oxidation of malate to oxaloacetate
Gene Name:: mdh
Uniprot ID:: P61889
Molecular weight:: 32337

Reactions

(S)-malate + NAD(+) = oxaloacetate + NADH.

Protein Details

3. Putative aliphatic sulfonates transport permease protein ssuC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: ssuC
Uniprot ID:: P75851
Molecular weight:: 28925

Transporters

Protein Details

1. Putative aliphatic sulfonates transport permease protein ssuC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: ssuC
Uniprot ID:: P75851
Molecular weight:: 28925

3-Sulfopyruvic acid (ECMDB21002) (M2MDB001422)

Structure for #<Compound:0xa7ac8198>

Enzymes

Reactions

Reactions

Transporters