ECMDB: (2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate (ECMDB23052) (M2MDB003442)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (1)

Record Information

Version

2.0

Creation Date

2012-10-10 12:14:10 -0600

Update Date

2015-06-03 17:25:49 -0600

Secondary Accession Numbers

ECMDB23052

Identification

Name:

(2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate

Description

(2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate is an intermediate in methylcitrate metabolism. It is involved in the reaction propinoyl-CoA + H2O + oxaloacetate = (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA which is mediated by the enzyme: 2-methylcitrate synthase.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2R,3S)-2-hydroxybutane-1,2,3-tricarboxylic acid
2-Hydroxybutane-1,2,3-tricarboxylate
2-Hydroxybutane-1,2,3-tricarboxylic acid
2-Methylcitrate
2-Methylcitric acid
3-C-Carboxy-2,4-dideoxy-2-methyl-D-threo-pentarate
3-C-Carboxy-2,4-dideoxy-2-methyl-D-threo-pentaric acid

Chemical Formula:

C₇H₁₀O₇

Weight:

Average: 206.1501
Monoisotopic: 206.042652674

InChI Key:

YNOXCRMFGMSKIJ-WVBDSBKLSA-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,2R)-2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid

Traditional IUPAC Name:

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

SMILES:

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

Chemical Taxonomy

Description

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
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-methylcitric acid (CHEBI:30836 )

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	175 g/L	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	17.3 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:

Propionyl-CoA + Water + Oxalacetic acid > (2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate + CoA

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
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
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	30836
HMDB ID	Not Available
Pubchem Compound ID	439681
Kegg ID	C02225
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 2-methylcitrate synthase

General function:: Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:: Catalyzes the synthesis of 2-methylcitrate from propionyl-CoA and oxaloacetate. Also catalyzes the condensation of oxaloacetate with acetyl-CoA but with a lower specificity
Gene Name:: prpC
Uniprot ID:: P31660
Molecular weight:: 43102

Reactions

Propanoyl-CoA + H(2)O + oxaloacetate = (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA.

(2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate (ECMDB23052) (M2MDB003442)

Structure for #<Compound:0xafe23ce0>

Enzymes

Reactions