P. aeruginosa Metabolome Database: Meso-2,6-Diaminoheptanedioate (PAMDB002055)

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

PAMDB002055

Identification

Name:

Meso-2,6-Diaminoheptanedioate

Description:

Meso-2,6-diaminoheptanedioate is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). This particular compound is at a branch point in lysine biosynthesis where it is either the penultimate step in lysine biosynthesis in Pseudomonas aeruginosa (via diaminopimelate decarboxylase, LysA) or it can be directed towards the synthesis of peptidoglycan (via murE).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(2R,6S)-2,6-diaminoheptanedioate
(2R,6S)-2,6-diaminoheptanedioic acid
Meso-2,6-Diaminoheptanedioate
Meso-2,6-Diaminoheptanedioic acid
Meso-2,6-Diaminopimelate
Meso-2,6-Diaminopimelic acid
Meso-Diaminoheptanedioate
Meso-Diaminoheptanedioic acid
Meso-DPA

Chemical Formula:

C₇H₁₄N₂O₄

Average Molecular Weight:

190.1971

Monoisotopic Molecular Weight:

190.095356946

InChI Key:

GMKMEZVLHJARHF-SYDPRGILSA-N

InChI:

InChI=1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5+

CAS number:

922-54-3

IUPAC Name:

(2R,6S)-2,6-diaminoheptanedioic acid

Traditional IUPAC Name:

diaminopimelic acid

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

D-alpha-amino acids

Alternative Parents

Substituents

D-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2,6-diaminopimelic acid (CHEBI:16488 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	14.1 mg/mL	ALOGPS
logP	-4.1	ALOGPS
logP	-5.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	9.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	43.64 m³·mol^-1	ChemAxon
Polarizability	18.68 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:

Meso-2,6-Diaminoheptanedioate <> L-Lysine + Carbon dioxide
Diaminopimelic acid <> Meso-2,6-Diaminoheptanedioate
Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Meso-2,6-Diaminoheptanedioate <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
Meso-2,6-Diaminoheptanedioate + Hydrogen ion > L-Lysine + Carbon dioxide + L-Lysine
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + Meso-2,6-Diaminoheptanedioate + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate > Adenosine diphosphate + Phosphate + Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate + ADP

Pathways:

Lysine biosynthesis pae00300
Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
Peptidoglycan biosynthesis pae00550

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006w-1900000000-b0e4598bfac1f1042028	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-5900000000-3cf670544958e8c5e216	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-9200000000-cb92e651126ece5c413e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-c81ad78d33d56b184c0a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-1900000000-be9446a41a29ccfe478c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9500000000-737f0f27e617ae2e898e	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	30308
HMDB ID	Not Available
Pubchem Compound ID	99290
Kegg ID	C00680
ChemSpider ID	842
Wikipedia ID	Not Available
BioCyc ID	Not Available
Ligand Expo	API

Meso-2,6-Diaminoheptanedioate (PAMDB002055)

Structure for Meso-2,6-Diaminoheptanedioate (PAMDB002055)