P. aeruginosa Metabolome Database: (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate (PAMDB003441)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB003441

Identification

Name:

(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate

Description:

Tricarboxylate anion of (2S,3R)-3-hydroxybutane-1,2,3-tricarboxylic acid

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(2S,3S)-2-Hydroxybutane-1,2,3-tricarboxylic acid

Chemical Formula:

C₇H₁₀O₇

Average Molecular Weight:

206.1501

Monoisotopic Molecular Weight:

206.042652674

InChI Key:

YNOXCRMFGMSKIJ-NFNCENRGSA-N

InChI:

InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t3-,7+/m1/s1

CAS number:

Not Available

IUPAC Name:

(1S,2S)-2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid

Traditional IUPAC Name:

(2S,3S)-2-methylcitric acid

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-methylcitric acid (CHEBI:50948 )

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	175.0 mg/mL	ALOGPS
logP	-0.89	ALOGPS
logP	-0.78	ChemAxon
logS	-0.07	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.2 m³·mol^-1	ChemAxon
Polarizability	17.33 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:

Water + Oxalacetic acid + Propionyl-CoA <> Methylcitric acid + Coenzyme A + Hydrogen ion + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate > Cis-2-Methylaconitate + Water

Pathways:

Propanoate metabolism pae00640

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-be0da5c29220e9e50325	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05i0-9600000000-2bead66ba2514df6497f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1093-7900000000-e7a5530b8562d859e032	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0900-1910000000-0a84eb8e0df2e6eb450d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-07vi-4900000000-e89ea7de4d7e433cae1e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-c68ffdf8bf6f5380005e	View in MoNA

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	50948
HMDB ID	Not Available
Pubchem Compound ID	12898022
Kegg ID	Not Available
ChemSpider ID	21865819
Wikipedia ID	Not Available
BioCyc ID	Not Available

(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate (PAMDB003441)

Structure for (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate (PAMDB003441)