ChemFOnt: Showing chemical card for 2,3-Dihydroxy-5-methylthio-4-pentenoic acid (CFc000220651)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:54 UTC

Chemfont ID

CFc000220651

Molecule Identification

Common Name

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

Definition

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 SDF PDB SMILES InChI

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

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 29578721)

Source

Exogenous

Exogenous (HMDB: HMDB0240388)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	22 g/L	ALOGPS
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

External Links

HMDB ID

HMDB0240388

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

References

Synthesis Reference

Not Available

Showing chemical card for 2,3-Dihydroxy-5-methylthio-4-pentenoic acid (CFc000220651)

MOL for CFc000220651 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

3D MOL for CFc000220651 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

3D SDF for CFc000220651 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

3D-SDF for CFc000220651 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

PDB for CFc000220651 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

3D PDB for CFc000220651 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

SMILES for CFc000220651 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

INCHI for CFc000220651 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

Structure for CFc000220651 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)

3D Structure for CFc000220651 (2,3-Dihydroxy-5-methylthio-4-pentenoic acid)