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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:21:31 UTC

Update Date

2023-02-21 17:25:35 UTC

HMDB ID

HMDB0037115

Secondary Accession Numbers

HMDB37115

Metabolite Identification

Common Name

(±)-2-Hydroxy-4-(methylthio)butanoic acid

Description

(±)-2-Hydroxy-4-(methylthio)butanoic 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 small amount of articles have been published on (±)-2-Hydroxy-4-(methylthio)butanoic acid.

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-hydroxy-4-(methylthio)butanoate	Generator
(+-)-2-Hydroxy-4-(methylthio)butyric acid	HMDB
2-Hydroxy-4-(methylthio) butanoic acid	HMDB
2-Hydroxy-4-(methylthio)-butanoic acid	HMDB
2-Hydroxy-4-(methylthio)-butyric acid	HMDB
2-Hydroxy-4-(methylthio)butanoic acid	HMDB
2-Hydroxy-4-(methylthio)butyric acid	HMDB
4857-44-7 (Calcium[2:1] salt)	HMDB
Alimet	HMDB, MeSH
alpha-Hydroxy-gamma-(methylmercapto)butyric acid	HMDB
alpha-Hydroxy-gamma-(methylthio)butyric acid	HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid	HMDB, MeSH
Desmeninol	HMDB
gamma-(methylthio)-alpha-Hydroxybutyric acid	HMDB
Methionine hydroxy analog	HMDB, MeSH
MHA	HMDB
Mha acid	HMDB
Mha-fa	HMDB
(+-)-Isomer OF alpha-hydroxy-gamma-methylmercaptobutyric acid	MeSH, HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, calcium salt(+-)-isomer	MeSH, HMDB
2-Hydroxy-4-methylthiobutanoic acid	MeSH, HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, calcium salt	MeSH, HMDB
2-Hydroxy-4-methylthiobutyrate	MeSH, HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, monosodium salt (S)-isomer	MeSH, HMDB
alpha-Hydroxymethionine	MeSH, HMDB
4-methylthio-2-Hydroxybutyrate	MeSH, HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, calcium salt (2:1)	MeSH, HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, monosodium salt	MeSH, HMDB
alpha-Hydroxy-gamma-methylthiobutyrate	MeSH, HMDB
2-Hydroxy-4-(methylthio)butanoate	Generator

Chemical Formula

C₅H₁₀O₃S

Average Molecular Weight

150.196

Monoisotopic Molecular Weight

150.035064876

IUPAC Name

2-hydroxy-4-(methylsulfanyl)butanoic acid

Traditional Name

methionine hydroxy analog

CAS Registry Number

120-91-2

SMILES

CSCCC(O)C(O)=O

InChI Identifier

InChI=1S/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)

InChI Key

ONFOSYPQQXJWGS-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

Hydroxy fatty acid
Thia fatty acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Dialkylthioether
Sulfenyl compound
Thioether
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organosulfur compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0037115)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0037115)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037115)

Source

Endogenous

Endogenous (HMDB: HMDB0037115)

Animal

Animal (HMDB: HMDB0037115)

Exogenous

Food

Food (HMDB: HMDB0037115)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037115)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037115)

Cellular process

Cell signaling (HMDB: HMDB0037115)

Biochemical process

Lipid transport (HMDB: HMDB0037115)

Role

Biological role

Energy storage (HMDB: HMDB0037115)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037115)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	250 °C	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	40.9 g/L	ALOGPS
logP	-0.4	ALOGPS
logP	0.18	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.93 m³·mol⁻¹	ChemAxon
Polarizability	15.09 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]+	130.776	31661259
DarkChem	[M-H]-	126.92	31661259
DeepCCS	[M+H]+	132.136	30932474
DeepCCS	[M-H]-	129.372	30932474
DeepCCS	[M-2H]-	165.73	30932474
DeepCCS	[M+Na]+	140.495	30932474
AllCCS	[M+H]+	133.7	32859911
AllCCS	[M+H-H2O]+	129.8	32859911
AllCCS	[M+NH4]+	137.3	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	134.8	32859911
AllCCS	[M+Na-2H]-	137.5	32859911
AllCCS	[M+HCOO]-	140.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-2-Hydroxy-4-(methylthio)butanoic acid	CSCCC(O)C(O)=O	2597.4	Standard polar	33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid	CSCCC(O)C(O)=O	1278.0	Standard non polar	33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid	CSCCC(O)C(O)=O	1415.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-2-Hydroxy-4-(methylthio)butanoic acid,1TMS,isomer #1	CSCCC(O[Si](C)(C)C)C(=O)O	1415.7	Semi standard non polar	33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid,1TMS,isomer #2	CSCCC(O)C(=O)O[Si](C)(C)C	1363.7	Semi standard non polar	33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid,2TMS,isomer #1	CSCCC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1451.2	Semi standard non polar	33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid,1TBDMS,isomer #1	CSCCC(O[Si](C)(C)C(C)(C)C)C(=O)O	1651.1	Semi standard non polar	33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid,1TBDMS,isomer #2	CSCCC(O)C(=O)O[Si](C)(C)C(C)(C)C	1605.9	Semi standard non polar	33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid,2TBDMS,isomer #1	CSCCC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1907.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-08i3-9200000000-b3f347c37bb602b8bb45	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00bi-9350000000-44bc7640c746eddc9889	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic 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 - (±)-2-Hydroxy-4-(methylthio)butanoic acid 10V, Negative-QTOF	splash10-0002-9100000000-88410fbd7b98e54f151e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 20V, Negative-QTOF	splash10-0002-9000000000-34be18dc4b552cce009e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 40V, Negative-QTOF	splash10-0002-9000000000-ca06cb2a413f50f341e0	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 10V, Positive-QTOF	splash10-0ue9-1900000000-dd2e58391a4c5f61dcd5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 20V, Positive-QTOF	splash10-056r-9700000000-8b98bae25421e4ce82fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 40V, Positive-QTOF	splash10-06vr-9000000000-7372f5d3aafd65f14b51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 10V, Negative-QTOF	splash10-0002-7900000000-3be7113c98ed23388528	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 20V, Negative-QTOF	splash10-0002-9300000000-b2110ea4fabace846c65	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 40V, Negative-QTOF	splash10-0002-9000000000-860ffaaedb18b65817fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 10V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 20V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 40V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 10V, Positive-QTOF	splash10-0a59-6900000000-7ef5ccb88b6ef1b9a20d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 20V, Positive-QTOF	splash10-03dr-9300000000-c248fe9ce5cc0b99282c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 40V, Positive-QTOF	splash10-03di-9000000000-9563ed6a85515f3e490e	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016108

KNApSAcK ID

Not Available

Chemspider ID

10946

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11427

PDB ID

Not Available

ChEBI ID

Not Available

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (±)-2-Hydroxy-4-(methylthio)butanoic acid (HMDB0037115)

MOL for HMDB0037115 ((±)-2-Hydroxy-4-(methylthio)butanoic acid)

3D MOL for HMDB0037115 ((±)-2-Hydroxy-4-(methylthio)butanoic acid)

3D SDF for HMDB0037115 ((±)-2-Hydroxy-4-(methylthio)butanoic acid)

3D-SDF for HMDB0037115 ((±)-2-Hydroxy-4-(methylthio)butanoic acid)

PDB for HMDB0037115 ((±)-2-Hydroxy-4-(methylthio)butanoic acid)

3D PDB for HMDB0037115 ((±)-2-Hydroxy-4-(methylthio)butanoic acid)

SMILES for HMDB0037115 ((±)-2-Hydroxy-4-(methylthio)butanoic acid)

INCHI for HMDB0037115 ((±)-2-Hydroxy-4-(methylthio)butanoic acid)

Structure for HMDB0037115 ((±)-2-Hydroxy-4-(methylthio)butanoic acid)

3D Structure for HMDB0037115 ((±)-2-Hydroxy-4-(methylthio)butanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra