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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-09-18 20:45:41 UTC

Update Date

2022-03-07 03:18:16 UTC

HMDB ID

HMDB0240388

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,3-Dihydroxy-5-methylthio-4-pentenoic acid

Description

2,3-Dihydroxy-5-methylthio-4-pentenoic acid (DMTPA) is a hydroxy fatty acid with a thioenolether group. DMTPA was previously an unknown potential plasma biomarker for glomerular filtration rate (GFR) but its structure has since been elucidated (PMID: 29578721 ). DMTPA is possibly involved in the methionine salvage pathway (MSP) and may potentially be synthesized from methylthioadenosine (MTA). MTA is a byproduct of S-adenosylmethionine (SAM) during polyamine biosynthesis.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-Dihydroxy-5-methylthio-4-pentenoate	Generator
(2R,3R,4E)-2,3-Dihydroxy-5-(methylsulfanyl)pent-4-enoate	HMDB
(2R,3R,4E)-2,3-Dihydroxy-5-(methylsulphanyl)pent-4-enoate	HMDB
(2R,3R,4E)-2,3-Dihydroxy-5-(methylsulphanyl)pent-4-enoic acid	HMDB
(2R,3R)-2,3-Dihydroxy-5-methylthio-4-pentenoic acid	HMDB
DMTPA	HMDB
trans-DMTPA	HMDB

Chemical Formula

C₆H₁₀O₄S

Average Molecular Weight

178.2

Monoisotopic Molecular Weight

178.029979976

IUPAC Name

(2R,3R,4E)-2,3-dihydroxy-5-(methylsulfanyl)pent-4-enoic acid

Traditional Name

(2R,3R,4E)-2,3-dihydroxy-5-(methylsulfanyl)pent-4-enoic acid

CAS Registry Number

2226539-09-7

SMILES

CS\C=C\[C@@H](O)[C@@H](O)C(O)=O

InChI Identifier

InChI=1S/C6H10O4S/c1-11-3-2-4(7)5(8)6(9)10/h2-5,7-8H,1H3,(H,9,10)/b3-2+/t4-,5-/m1/s1

InChI Key

XMZBEAXQGSBWLG-BKDNXVRYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Short-chain hydroxy acid
Hydroxy fatty acid
Beta-hydroxy acid
Unsaturated fatty acid
Monosaccharide
Hydroxy acid
Alpha-hydroxy acid
Thioenolether
Secondary alcohol
1,2-diol
Sulfenyl compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 29578721)

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	-0.54	ALOGPS
logP	-0.49	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	42.07 m³·mol⁻¹	ChemAxon
Polarizability	16.9 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]+	137.247	30932474
DeepCCS	[M-H]-	134.853	30932474
DeepCCS	[M-2H]-	168.779	30932474
DeepCCS	[M+Na]+	144.064	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydroxy-5-methylthio-4-pentenoic acid	CS\C=C\[C@@H](O)[C@@H](O)C(O)=O	2926.9	Standard polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid	CS\C=C\[C@@H](O)[C@@H](O)C(O)=O	1600.2	Standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid	CS\C=C\[C@@H](O)[C@@H](O)C(O)=O	1633.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,1TMS,isomer #1	CS/C=C/[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1598.2	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,1TMS,isomer #2	CS/C=C/[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1586.2	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,1TMS,isomer #3	CS/C=C/[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1529.7	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,2TMS,isomer #1	CS/C=C/[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1670.5	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,2TMS,isomer #2	CS/C=C/[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1657.1	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,2TMS,isomer #3	CS/C=C/[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1641.2	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,3TMS,isomer #1	CS/C=C/[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1695.7	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,1TBDMS,isomer #1	CS/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	1844.9	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,1TBDMS,isomer #2	CS/C=C/[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	1835.5	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,1TBDMS,isomer #3	CS/C=C/[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	1765.6	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,2TBDMS,isomer #1	CS/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2137.0	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,2TBDMS,isomer #2	CS/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2113.4	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,2TBDMS,isomer #3	CS/C=C/[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2085.1	Semi standard non polar	33892256
2,3-Dihydroxy-5-methylthio-4-pentenoic acid,3TBDMS,isomer #1	CS/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2363.7	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 - 2,3-Dihydroxy-5-methylthio-4-pentenoic 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 - 2,3-Dihydroxy-5-methylthio-4-pentenoic acid 10V, Negative-QTOF	splash10-004j-9100000000-8f31a7fa8169426b0310	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-5-methylthio-4-pentenoic acid 20V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-5-methylthio-4-pentenoic acid 40V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-5-methylthio-4-pentenoic acid 10V, Positive-QTOF	splash10-01q9-4900000000-144d388b6a538a20e5df	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-5-methylthio-4-pentenoic acid 20V, Positive-QTOF	splash10-03di-5900000000-4bc1a350d0447d15a705	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-5-methylthio-4-pentenoic acid 40V, Positive-QTOF	splash10-01ot-9000000000-bb32d0ffb145ab711ecd	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

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	29578721	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154603736

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

Zhang Q, Ford LA, Evans AM, Toal DR: Identification of an Endogenous Organosulfur Metabolite by Interpretation of Mass Spectrometric Data. Org Lett. 2018 Apr 6;20(7):2100-2103. doi: 10.1021/acs.orglett.8b00664. Epub 2018 Mar 26. [PubMed:29578721 ]

Showing metabocard for 2,3-Dihydroxy-5-methylthio-4-pentenoic acid (HMDB0240388)

MOL for HMDB0240388 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

3D MOL for HMDB0240388 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

3D SDF for HMDB0240388 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

3D-SDF for HMDB0240388 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

PDB for HMDB0240388 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

3D PDB for HMDB0240388 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

SMILES for HMDB0240388 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

INCHI for HMDB0240388 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

Structure for HMDB0240388 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

3D Structure for HMDB0240388 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra