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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:47:56 UTC

Update Date

2021-09-26 23:08:28 UTC

HMDB ID

HMDB0254466

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Mercaptosuccinic acid

Description

Mercaptosuccinic acid, also known as 2-mercaptosuccinate or 2-thiomalic acid, belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain. Based on a literature review a significant number of articles have been published on Mercaptosuccinic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Mercaptosuccinic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Mercaptosuccinic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

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-Mercaptosuccinic acid	ChEBI
2-Sulfanylsuccinic acid	ChEBI
2-Thiomalic acid	ChEBI
alpha-Mercaptosuccinic acid	ChEBI
Monomercaptosuccinic acid	ChEBI
2-Mercaptosuccinate	Generator
2-Sulfanylsuccinate	Generator
2-Sulphanylsuccinate	Generator
2-Sulphanylsuccinic acid	Generator
2-Thiomalate	Generator
a-Mercaptosuccinate	Generator
a-Mercaptosuccinic acid	Generator
alpha-Mercaptosuccinate	Generator
Α-mercaptosuccinate	Generator
Α-mercaptosuccinic acid	Generator
Monomercaptosuccinate	Generator
Mercaptosuccinate	Generator

Chemical Formula

C₄H₆O₄S

Average Molecular Weight

150.15

Monoisotopic Molecular Weight

149.998679847

IUPAC Name

2-sulfanylbutanedioic acid

Traditional Name

mercaptosuccinic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC(S)C(O)=O

InChI Identifier

InChI=1S/C4H6O4S/c5-3(6)1-2(9)4(7)8/h2,9H,1H2,(H,5,6)(H,7,8)

InChI Key

NJRXVEJTAYWCQJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Thia fatty acids

Alternative Parents

Substituents

Thia fatty acid
Dicarboxylic acid or derivatives
2-mercaptocarboxylic acid
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

C4-dicarboxylic acid (CHEBI:38705 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	0.11	ALOGPS
logP	-0.07	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.65	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31 m³·mol⁻¹	ChemAxon
Polarizability	12.87 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
DeepCCS	[M+H]+	129.487	30932474
DeepCCS	[M-H]-	126.588	30932474
DeepCCS	[M-2H]-	163.102	30932474
DeepCCS	[M+Na]+	138.051	30932474
AllCCS	[M+H]+	133.6	32859911
AllCCS	[M+H-H2O]+	129.7	32859911
AllCCS	[M+NH4]+	137.4	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	128.4	32859911
AllCCS	[M+Na-2H]-	131.2	32859911
AllCCS	[M+HCOO]-	134.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mercaptosuccinic acid	OC(=O)CC(S)C(O)=O	2384.5	Standard polar	33892256
Mercaptosuccinic acid	OC(=O)CC(S)C(O)=O	1044.9	Standard non polar	33892256
Mercaptosuccinic acid	OC(=O)CC(S)C(O)=O	1384.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mercaptosuccinic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(S[Si](C)(C)C)C(=O)O[Si](C)(C)C	1641.3	Semi standard non polar	33892256
Mercaptosuccinic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(S[Si](C)(C)C)C(=O)O[Si](C)(C)C	1592.5	Standard non polar	33892256
Mercaptosuccinic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(S[Si](C)(C)C)C(=O)O[Si](C)(C)C	1698.0	Standard polar	33892256
Mercaptosuccinic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(S[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2267.1	Semi standard non polar	33892256
Mercaptosuccinic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(S[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2200.9	Standard non polar	33892256
Mercaptosuccinic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(S[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2133.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9800000000-131adbdf5e291a30466f	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptosuccinic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	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 - Mercaptosuccinic acid 10V, Positive-QTOF	splash10-0a4i-2900000000-90a321b8dcba2142e376	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptosuccinic acid 20V, Positive-QTOF	splash10-052u-9300000000-e9e01526004142ab2ff3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptosuccinic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-0a18bba5ccbe54e11bdb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptosuccinic acid 10V, Negative-QTOF	splash10-01bi-7900000000-541eb0b15679cca4fee3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptosuccinic acid 20V, Negative-QTOF	splash10-0a59-9100000000-647d375cd21be6cddad0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptosuccinic acid 40V, Negative-QTOF	splash10-0a5i-9000000000-7f949d4e620a7715084a	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6032

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thiomalic acid

METLIN ID

Not Available

PubChem Compound

6268

PDB ID

Not Available

ChEBI ID

38705

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Mercaptosuccinic acid (HMDB0254466)

MOL for HMDB0254466 (Mercaptosuccinic acid)

3D MOL for HMDB0254466 (Mercaptosuccinic acid)

3D SDF for HMDB0254466 (Mercaptosuccinic acid)

3D-SDF for HMDB0254466 (Mercaptosuccinic acid)

PDB for HMDB0254466 (Mercaptosuccinic acid)

3D PDB for HMDB0254466 (Mercaptosuccinic acid)

SMILES for HMDB0254466 (Mercaptosuccinic acid)

INCHI for HMDB0254466 (Mercaptosuccinic acid)

Structure for HMDB0254466 (Mercaptosuccinic acid)

3D Structure for HMDB0254466 (Mercaptosuccinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra