P. aeruginosa Metabolome Database: D-Erythro-3-Methylmalate (PAMDB000985)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000985

Identification

Name:

D-Erythro-3-Methylmalate

Description:

D-erythro-3-methylmalate is a member of the chemical class known as Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(2R,3S)-2-hydroxy-3-methylbutanedioate
(2R,3S)-2-hydroxy-3-methylbutanedioic acid
(2R,3S)-3-methylmalate
(2R,3S)-3-methylmalic acid
D-Erythro-3-methylmalate
D-Erythro-3-methylmalic acid

Chemical Formula:

C₅H₈O₅

Average Molecular Weight:

148.114

Monoisotopic Molecular Weight:

148.037173366

InChI Key:

NPYQJIHHTGFBLN-STHAYSLISA-N

InChI:

InChI=1S/C5H8O5/c1-2(4(7)8)3(6)5(9)10/h2-3,6H,1H3,(H,7,8)(H,9,10)/t2-,3+/m0/s1

CAS number:

Not Available

IUPAC Name:

(2R,3S)-2-hydroxy-3-methylbutanedioic acid

Traditional IUPAC Name:

D-erythro-3-methylmalate

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound 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

Hydroxy fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Branched fatty acid
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

erythro-3-methylmalic acid (CHEBI:27394 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	154.0 mg/mL	ALOGPS
logP	-0.33	ALOGPS
logP	-0.57	ChemAxon
logS	0.02	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	29.45 m³·mol^-1	ChemAxon
Polarizability	12.74 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

2-Ketobutyric acid + Carbon dioxide + NADH + Hydrogen ion <> D-Erythro-3-Methylmalate + NAD
Citraconic acid + Water <> D-Erythro-3-Methylmalate

Pathways:

C5-Branched dibasic acid metabolism pae00660
Valine, leucine and isoleucine biosynthesis pae00290

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f8a-3900000000-0757759d8479c38634f0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9200000000-aafee9f80ad3d78f7d1e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-87d1de119df5d3bfdb12	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-2900000000-204aa7e58ea1ab8f7640	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pi9-9500000000-0dca374ca1bbb677091b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-b2f353c995a6f56458b1	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	27394
HMDB ID	Not Available
Pubchem Compound ID	440892
Kegg ID	C06032
ChemSpider ID	389722
Wikipedia ID	Not Available
BioCyc ID	Not Available

D-Erythro-3-Methylmalate (PAMDB000985)

Structure for D-Erythro-3-Methylmalate (PAMDB000985)