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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10) Show 10 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:38 UTC

HMDB ID

HMDB0001368

Secondary Accession Numbers

HMDB01368

Metabolite Identification

Common Name

3-Mercaptopyruvic acid

Description

3-Mercaptopyruvic acid, also known as 3-mercapto-2-oxopropanoate or beta-thiopyruvate, 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 intermediate in cysteine metabolism. 3-Mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 3-mercaptopyruvic acid participates in a number of enzymatic reactions. In particular, 3-mercaptopyruvic acid and cyanide can be converted into pyruvic acid and thiocyanate; which is mediated by the enzyme 3-mercaptopyruvate sulfurtransferase. In addition, 3-mercaptopyruvic acid can be biosynthesized from 3-mercaptolactic acid; which is mediated by the enzyme L-lactate dehydrogenase. It has been studied as a potential treatment for cyanide poisoning, but its half-life is too short for it to be clinically effective. In humans, 3-mercaptopyruvic acid is involved in cystinosis, ocular nonnephropathic. Outside of the human body, 3-mercaptopyruvic acid has been detected, but not quantified in several different foods, such as lima beans, spinachs, shallots, mexican groundcherries, and white lupines. This could make 3-mercaptopyruvic 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 Stereo Labels

Synonyms

Value	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

Chemical Formula

C₃H₄O₃S

Average Molecular Weight

120.127

Monoisotopic Molecular Weight

119.988114684

IUPAC Name

2-oxo-3-sulfanylpropanoic acid

Traditional Name

β-mercaptopyruvic acid

CAS Registry Number

2464-23-5

SMILES

OC(=O)C(=O)CS

InChI Identifier

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

InChI Key

OJOLFAIGOXZBCI-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
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

Not Available

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	123.678	31661259
DarkChem	[M-H]-	116.782	31661259
AllCCS	[M+H]+	128.59	32859911
AllCCS	[M-H]-	126.921	32859911
DeepCCS	[M+H]+	123.602	30932474
DeepCCS	[M-H]-	121.702	30932474
DeepCCS	[M-2H]-	157.297	30932474
DeepCCS	[M+Na]+	131.843	30932474
AllCCS	[M+H]+	128.6	32859911
AllCCS	[M+H-H2O]+	124.4	32859911
AllCCS	[M+NH4]+	132.5	32859911
AllCCS	[M+Na]+	133.6	32859911
AllCCS	[M-H]-	126.9	32859911
AllCCS	[M+Na-2H]-	130.8	32859911
AllCCS	[M+HCOO]-	135.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.15 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3035 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.12 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	132.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1502.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	431.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	127.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	303.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	103.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	359.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	483.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	661.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	796.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	149.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1077.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	313.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	763.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	330.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	275.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Mercaptopyruvic acid	OC(=O)C(=O)CS	2243.4	Standard polar	33892256
3-Mercaptopyruvic acid	OC(=O)C(=O)CS	1526.8	Standard non polar	33892256
3-Mercaptopyruvic acid	OC(=O)C(=O)CS	1091.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Mercaptopyruvic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CS	1154.9	Semi standard non polar	33892256
3-Mercaptopyruvic acid,1TMS,isomer #2	C[Si](C)(C)SCC(=O)C(=O)O	1329.6	Semi standard non polar	33892256
3-Mercaptopyruvic acid,1TMS,isomer #3	C[Si](C)(C)OC(=CS)C(=O)O	1304.1	Semi standard non polar	33892256
3-Mercaptopyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C	1433.2	Semi standard non polar	33892256
3-Mercaptopyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C	1379.7	Standard non polar	33892256
3-Mercaptopyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C	1509.4	Standard polar	33892256
3-Mercaptopyruvic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C	1467.7	Semi standard non polar	33892256
3-Mercaptopyruvic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C	1462.3	Standard non polar	33892256
3-Mercaptopyruvic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C	1478.6	Standard polar	33892256
3-Mercaptopyruvic acid,2TMS,isomer #3	C[Si](C)(C)OC(=CS[Si](C)(C)C)C(=O)O	1530.1	Semi standard non polar	33892256
3-Mercaptopyruvic acid,2TMS,isomer #3	C[Si](C)(C)OC(=CS[Si](C)(C)C)C(=O)O	1527.9	Standard non polar	33892256
3-Mercaptopyruvic acid,2TMS,isomer #3	C[Si](C)(C)OC(=CS[Si](C)(C)C)C(=O)O	1696.9	Standard polar	33892256
3-Mercaptopyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C)O[Si](C)(C)C	1565.2	Semi standard non polar	33892256
3-Mercaptopyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C)O[Si](C)(C)C	1471.0	Standard non polar	33892256
3-Mercaptopyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C)O[Si](C)(C)C	1516.9	Standard polar	33892256
3-Mercaptopyruvic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS	1417.6	Semi standard non polar	33892256
3-Mercaptopyruvic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)SCC(=O)C(=O)O	1585.6	Semi standard non polar	33892256
3-Mercaptopyruvic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CS)C(=O)O	1542.2	Semi standard non polar	33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C(C)(C)C	1883.1	Semi standard non polar	33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C(C)(C)C	1825.3	Standard non polar	33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C(C)(C)C	1793.1	Standard polar	33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C(C)(C)C	1883.6	Semi standard non polar	33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C(C)(C)C	1890.7	Standard non polar	33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C(C)(C)C	1756.8	Standard polar	33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CS[Si](C)(C)C(C)(C)C)C(=O)O	1961.7	Semi standard non polar	33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CS[Si](C)(C)C(C)(C)C)C(=O)O	1949.3	Standard non polar	33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CS[Si](C)(C)C(C)(C)C)C(=O)O	1904.8	Standard polar	33892256
3-Mercaptopyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2188.3	Semi standard non polar	33892256
3-Mercaptopyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2057.9	Standard non polar	33892256
3-Mercaptopyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1929.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercaptopyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9000000000-b81f8808977132c3a8ac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercaptopyruvic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9300000000-5100fd5cbb3bf9df1e75	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercaptopyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercaptopyruvic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Mercaptopyruvic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-003r-9200000000-f1e0c53958ad51dc0068	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Mercaptopyruvic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-001j-9000000000-60f6deb41f42078dd60c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Mercaptopyruvic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-001i-9000000000-5dc69d3b59bd15290aef	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Negative-QTOF	splash10-02t9-9000000000-e1511333b005fa911312	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Negative-QTOF	splash10-00kf-9000000000-65854057c742d34c8dbb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Negative-QTOF	splash10-006w-9000000000-66939f30bca1061b4b83	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Positive-QTOF	splash10-0fk9-2900000000-0da521157f8235fe7758	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Positive-QTOF	splash10-0fk9-7900000000-8c127be0565b54938cd2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Positive-QTOF	splash10-0ab9-9000000000-d4a8d07d451ba309b2e2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Negative-QTOF	splash10-014i-1900000000-849e74ceb9308736ba6d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Negative-QTOF	splash10-0gb9-2900000000-5a713232367a68a966a0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Negative-QTOF	splash10-0fk9-9300000000-564344466a63b943c6da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Negative-QTOF	splash10-006x-9200000000-95772f7f626a811df489	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Negative-QTOF	splash10-001i-9000000000-32551e3b5faf0b1e7000	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Negative-QTOF	splash10-001i-9000000000-572c315b879edca344fa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Positive-QTOF	splash10-00di-9400000000-8738d67598547a4b3429	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Positive-QTOF	splash10-00di-9000000000-4ba1ab7a6a1dc95bba23	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Positive-QTOF	splash10-0002-9000000000-6a9a04efc4b7bb2af1eb	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cysteine Metabolism
Beta-mercaptolactate-cysteine disulfiduria		Not Available
Cystinosis, ocular nonnephropathic		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0400-0.310 umol/mmol creatinine	Not Specified	Both	Normal	6945862	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.72 umol/mmol creatinine	Adult (>18 years old)	Female	Beta-mercaptolactate-cysteine Disulfiduria	6945862	details

Associated Disorders and Diseases

Disease References

Beta-mercaptolactate-cysteine Disulfiduria
Hannestad U, Martensson J, Sjodahl R, Sorbo B: 3-mercaptolactate cysteine disulfiduria: biochemical studies on affected and unaffected members of a family. Biochem Med. 1981 Aug;26(1):106-14. [PubMed:6945862 ]

Associated OMIM IDs

249650 (Beta-mercaptolactate-cysteine Disulfiduria)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030434

KNApSAcK ID

C00007464

Chemspider ID

KEGG Compound ID

C00957

BioCyc ID

3-MERCAPTO-PYRUVATE

BiGG ID

36476

Wikipedia Link

3-Mercaptopyruvic_acid

METLIN ID

6195

PubChem Compound

PDB ID

Not Available

ChEBI ID

16208

Food Biomarker Ontology

Not Available

VMH ID

MERCPPYR

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

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

L-Cysteine + Oxoglutaric acid → 3-Mercaptopyruvic acid + DL-Glutamate	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

L-Cysteine + Oxoglutaric acid → 3-Mercaptopyruvic acid + DL-Glutamate	details

Enzyme Details

3. Cystathionine gamma-lyase

General function:: Involved in pyridoxal phosphate binding
Specific function:: Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:: CTH
Uniprot ID:: P32929
Molecular weight:: 41259.91

Enzyme Details

4. 3-mercaptopyruvate sulfurtransferase

General function:: Involved in thiosulfate sulfurtransferase activity
Specific function:: Transfer of a sulfur ion to cyanide or to other thiol compounds. Also has weak rhodanese activity. May have a role in cyanide degradation or in thiosulfate biosynthesis.
Gene Name:: MPST
Uniprot ID:: P25325
Molecular weight:: 33178.15

Reactions

3-Mercaptopyruvic acid + Hydrogen cyanide → Pyruvic acid + Thiocyanate	details
3-Mercaptopyruvic acid + Sulfite → Thiosulfate + Pyruvic acid	details

Enzyme Details

5. L-lactate dehydrogenase A-like 6A

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Displays an lactate dehydrogenase activity. Significantly increases the transcriptional activity of JUN, when overexpressed.
Gene Name:: LDHAL6A
Uniprot ID:: Q6ZMR3
Molecular weight:: 36507.015

Reactions

3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Ion	details

Enzyme Details

6. Thiosulfate sulfurtransferase

General function:: Involved in thiosulfate sulfurtransferase activity
Specific function:: Formation of iron-sulfur complexes, cyanide detoxification or modification of sulfur-containing enzymes. Other thiol compounds, besides cyanide, can act as sulfur ion acceptors. Also has weak mercaptopyruvate sulfurtransferase (MST) activity (By similarity). Together with MRPL18, acts as a mitochondrial import factor for the cytosolic 5S rRNA. Only the nascent unfolded cytoplasmic form is able to bind to the 5S rRNA.
Gene Name:: TST
Uniprot ID:: Q16762
Molecular weight:: 33428.69

Reactions

3-Mercaptopyruvic acid + Sulfite → Thiosulfate + Pyruvic acid	details
Hydrogen cyanide + 3-Mercaptopyruvic acid → Thiocyanate + Pyruvic acid	details

Enzyme Details

7. L-lactate dehydrogenase B chain

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Not Available
Gene Name:: LDHB
Uniprot ID:: P07195
Molecular weight:: 36638.225

Reactions

3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Ion	details

Enzyme Details

8. L-lactate dehydrogenase C chain

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Possible role in sperm motility.
Gene Name:: LDHC
Uniprot ID:: P07864
Molecular weight:: 36310.965

Reactions

3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Ion	details

Enzyme Details

9. L-lactate dehydrogenase A chain

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Not Available
Gene Name:: LDHA
Uniprot ID:: P00338
Molecular weight:: 30204.975

Reactions

3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Ion	details

Enzyme Details

10. L-lactate dehydrogenase A-like 6B

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Not Available
Gene Name:: LDHAL6B
Uniprot ID:: Q9BYZ2
Molecular weight:: 41942.53

Reactions

3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Ion	details

Showing metabocard for 3-Mercaptopyruvic acid (HMDB0001368)

MOL for HMDB0001368 (3-Mercaptopyruvic acid)

3D MOL for HMDB0001368 (3-Mercaptopyruvic acid)

3D SDF for HMDB0001368 (3-Mercaptopyruvic acid)

3D-SDF for HMDB0001368 (3-Mercaptopyruvic acid)

PDB for HMDB0001368 (3-Mercaptopyruvic acid)

3D PDB for HMDB0001368 (3-Mercaptopyruvic acid)

SMILES for HMDB0001368 (3-Mercaptopyruvic acid)

INCHI for HMDB0001368 (3-Mercaptopyruvic acid)

Structure for HMDB0001368 (3-Mercaptopyruvic acid)

3D Structure for HMDB0001368 (3-Mercaptopyruvic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

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