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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 09:37:36 UTC

Update Date

2020-02-26 21:24:55 UTC

HMDB ID

HMDB0004045

Secondary Accession Numbers

HMDB0060174
HMDB04045
HMDB60174

Metabolite Identification

Common Name

3-Sulfopyruvic acid

Description

3-Sulfopyruvic acid, also known as 3-sulfopyruvate, 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. A carboxyalkanesulfonic acid comprising pyruvic acid with a sulfo group attached at the C-3 position. 3-Sulfopyruvic acid is an extremely strong acidic compound (based on its pKa). 3-Sulfopyruvic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 3-Sulfopyruvic acid has been detected, but not quantified in, several different foods, such as yautia, nanking cherries, cloves, acerola, and strawberries. This could make 3-sulfopyruvic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Carboxy-2-oxoethanesulfonic acid	ChEBI
3-Sulfopyruvate	ChEBI
beta-Sulfopyruvic acid	ChEBI
SULFopyruvATE	ChEBI
2-Carboxy-2-oxoethanesulfonate	Generator
2-Carboxy-2-oxoethanesulphonate	Generator
2-Carboxy-2-oxoethanesulphonic acid	Generator
3-Sulphopyruvate	Generator
3-Sulphopyruvic acid	Generator
b-Sulfopyruvate	Generator
b-Sulfopyruvic acid	Generator
b-Sulphopyruvate	Generator
b-Sulphopyruvic acid	Generator
beta-Sulfopyruvate	Generator
beta-Sulphopyruvate	Generator
beta-Sulphopyruvic acid	Generator
Β-sulfopyruvate	Generator
Β-sulfopyruvic acid	Generator
Β-sulphopyruvate	Generator
Β-sulphopyruvic acid	Generator
Sulfopyruvic acid	Generator
Sulphopyruvate	Generator
Sulphopyruvic acid	Generator
2-oxo-3-SulfO-propanoate	HMDB
2-oxo-3-SulfO-propanoic acid	HMDB
2-oxo-3-Sulfopropanoate	HMDB
2-oxo-3-Sulfopropanoic acid	HMDB
3-Sulfonatopyruvate	HMDB

Chemical Formula

C₃H₄O₆S

Average Molecular Weight

168.125

Monoisotopic Molecular Weight

167.97285855

IUPAC Name

2-oxo-3-sulfopropanoic acid

Traditional Name

sulfopyruvate

CAS Registry Number

98022-26-5

SMILES

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

InChI Identifier

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

InChI Key

BUTHMSUEBYPMKJ-UHFFFAOYSA-N

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 )

Ontology

Ingestion

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.701	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.9 g/L	ALOGPS
logP	10^(-1.5) g/L	ALOGPS
logP	10^(-0.74) g/L	ChemAxon
logS	10^(-1.1) g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.723	31661259
DarkChem	[M-H]-	129.313	31661259

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Sulfopyruvic acid	OC(=O)C(=O)CS(O)(=O)=O	2662.7	Standard polar	33892256
3-Sulfopyruvic acid	OC(=O)C(=O)CS(O)(=O)=O	890.0	Standard non polar	33892256
3-Sulfopyruvic acid	OC(=O)C(=O)CS(O)(=O)=O	1469.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Sulfopyruvic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CS(=O)(=O)O	1508.3	Semi standard non polar	33892256
3-Sulfopyruvic acid,1TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)CC(=O)C(=O)O	1590.8	Semi standard non polar	33892256
3-Sulfopyruvic acid,1TMS,isomer #3	C[Si](C)(C)OC(=CS(=O)(=O)O)C(=O)O	1647.4	Semi standard non polar	33892256
3-Sulfopyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CS(=O)(=O)O[Si](C)(C)C	1684.3	Semi standard non polar	33892256
3-Sulfopyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CS(=O)(=O)O[Si](C)(C)C	1677.8	Standard non polar	33892256
3-Sulfopyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CS(=O)(=O)O[Si](C)(C)C	2145.4	Standard polar	33892256
3-Sulfopyruvic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(=CS(=O)(=O)O)O[Si](C)(C)C	1697.3	Semi standard non polar	33892256
3-Sulfopyruvic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(=CS(=O)(=O)O)O[Si](C)(C)C	1763.3	Standard non polar	33892256
3-Sulfopyruvic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(=CS(=O)(=O)O)O[Si](C)(C)C	2484.4	Standard polar	33892256
3-Sulfopyruvic acid,2TMS,isomer #3	C[Si](C)(C)OC(=CS(=O)(=O)O[Si](C)(C)C)C(=O)O	1800.9	Semi standard non polar	33892256
3-Sulfopyruvic acid,2TMS,isomer #3	C[Si](C)(C)OC(=CS(=O)(=O)O[Si](C)(C)C)C(=O)O	1780.1	Standard non polar	33892256
3-Sulfopyruvic acid,2TMS,isomer #3	C[Si](C)(C)OC(=CS(=O)(=O)O[Si](C)(C)C)C(=O)O	2340.4	Standard polar	33892256
3-Sulfopyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CS(=O)(=O)O[Si](C)(C)C)O[Si](C)(C)C	1784.4	Semi standard non polar	33892256
3-Sulfopyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CS(=O)(=O)O[Si](C)(C)C)O[Si](C)(C)C	1902.5	Standard non polar	33892256
3-Sulfopyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CS(=O)(=O)O[Si](C)(C)C)O[Si](C)(C)C	2091.9	Standard polar	33892256
3-Sulfopyruvic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS(=O)(=O)O	1778.8	Semi standard non polar	33892256
3-Sulfopyruvic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)CC(=O)C(=O)O	1862.2	Semi standard non polar	33892256
3-Sulfopyruvic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CS(=O)(=O)O)C(=O)O	1906.5	Semi standard non polar	33892256
3-Sulfopyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS(=O)(=O)O[Si](C)(C)C(C)(C)C	2146.2	Semi standard non polar	33892256
3-Sulfopyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS(=O)(=O)O[Si](C)(C)C(C)(C)C	2248.1	Standard non polar	33892256
3-Sulfopyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS(=O)(=O)O[Si](C)(C)C(C)(C)C	2299.0	Standard polar	33892256
3-Sulfopyruvic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)(=O)O)O[Si](C)(C)C(C)(C)C	2165.2	Semi standard non polar	33892256
3-Sulfopyruvic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)(=O)O)O[Si](C)(C)C(C)(C)C	2261.5	Standard non polar	33892256
3-Sulfopyruvic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)(=O)O)O[Si](C)(C)C(C)(C)C	2557.8	Standard polar	33892256
3-Sulfopyruvic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2234.0	Semi standard non polar	33892256
3-Sulfopyruvic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2309.4	Standard non polar	33892256
3-Sulfopyruvic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2444.1	Standard polar	33892256
3-Sulfopyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2421.2	Semi standard non polar	33892256
3-Sulfopyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2651.8	Standard non polar	33892256
3-Sulfopyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2370.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfopyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9300000000-8fb65d208d027ce47187	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfopyruvic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9310000000-852dd197381758581de3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfopyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 10V, Positive-QTOF	splash10-014i-0900000000-094511841526eb040890	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 20V, Positive-QTOF	splash10-0g4i-2900000000-77b615b663328d3fe524	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 40V, Positive-QTOF	splash10-006x-9500000000-bf672301532b1817de74	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 10V, Negative-QTOF	splash10-014i-0900000000-4e67b7b2992779903679	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 20V, Negative-QTOF	splash10-014i-3900000000-9801b0e1faeb0f73a93b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 40V, Negative-QTOF	splash10-00di-7900000000-7a1af7df664000361846	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 10V, Positive-QTOF	splash10-0udi-5900000000-8c6e190717a212c1f83b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 20V, Positive-QTOF	splash10-0006-9100000000-762dfd631fed0cc2e666	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 40V, Positive-QTOF	splash10-004l-9000000000-440cd593424b9672a3c7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 10V, Negative-QTOF	splash10-014i-0900000000-62e3604ba5cc3505465b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 20V, Negative-QTOF	splash10-0089-9600000000-fad73b53a872db46f577	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfopyruvic acid 40V, Negative-QTOF	splash10-0006-9000000000-ff8f9426210041ec9988	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02156

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440717

PDB ID

Not Available

ChEBI ID

16894

Food Biomarker Ontology

Not Available

VMH ID

3SPYR

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
Weinstein CL, Griffith OW: Cysteinesulfonate and beta-sulfopyruvate metabolism. Partitioning between decarboxylation, transamination, and reduction pathways. J Biol Chem. 1988 Mar 15;263(8):3735-43. [PubMed:3346220 ]

Enzymes

Enzyme Details

1. Aspartate aminotransferase, cytoplasmic

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Plays a key role in amino acid metabolism (By similarity).
Gene Name:: GOT1
Uniprot ID:: P17174
Molecular weight:: 46247.14

Reactions

Cysteic acid + Oxoglutaric acid → 3-Sulfopyruvic acid + L-Glutamic acid	details

Enzyme Details

2. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Reactions

Cysteic acid + Oxoglutaric acid → 3-Sulfopyruvic acid + L-Glutamic acid	details

Showing metabocard for 3-Sulfopyruvic acid (HMDB0004045)

MOL for HMDB0004045 (3-Sulfopyruvic acid)

3D MOL for HMDB0004045 (3-Sulfopyruvic acid)

3D SDF for HMDB0004045 (3-Sulfopyruvic acid)

3D-SDF for HMDB0004045 (3-Sulfopyruvic acid)

PDB for HMDB0004045 (3-Sulfopyruvic acid)

3D PDB for HMDB0004045 (3-Sulfopyruvic acid)

SMILES for HMDB0004045 (3-Sulfopyruvic acid)

INCHI for HMDB0004045 (3-Sulfopyruvic acid)

Structure for HMDB0004045 (3-Sulfopyruvic acid)

3D Structure for HMDB0004045 (3-Sulfopyruvic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions