ECMDB: Meso-2,6-Diaminoheptanedioate (ECMDB21665) (M2MDB002055)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)Transporters (1)XML

Proteins (1368)

Record Information

Version

2.0

Creation Date

2012-08-15 08:51:38 -0600

Update Date

2015-06-03 17:22:02 -0600

Secondary Accession Numbers

ECMDB21665

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 E. coli (via diaminopimelate decarboxylase, LysA) or it can be directed towards the synthesis of peptidoglycan (via murE).

Structure

MOL SDF PDB SMILES InChI

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

Weight:

Average: 190.1971
Monoisotopic: 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

Description

belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-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

L-alpha-amino acids

Alternative Parents

Substituents

D-alpha-amino acid
L-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organic oxide
Hydrocarbon derivative
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 g/L	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:

SMPDB Pathways:

Lysine biosynthesis	PW000771
peptidoglycan biosynthesis I	PW000906
peptidoglycan biosynthesis I 2	PW002062

KEGG Pathways:

Lysine biosynthesis ec00300
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Peptidoglycan biosynthesis ec00550

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
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
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	30308
HMDB ID	Not Available
Pubchem Compound ID	99290
Kegg ID	C00680
ChemSpider ID	842
Wikipedia ID	Diaminopimelic_acid
BioCyc ID	Not Available
Ligand Expo	API

Enzymes

Protein Details

1. Diaminopimelate decarboxylase

General function:: Involved in catalytic activity
Specific function:: Meso-2,6-diaminoheptanedioate = L-lysine + CO(2)
Gene Name:: lysA
Uniprot ID:: P00861
Molecular weight:: 46177

Reactions

Meso-2,6-diaminoheptanedioate = L-lysine + CO(2).

Protein Details

2. Diaminopimelate epimerase

General function:: Involved in diaminopimelate epimerase activity
Specific function:: LL-2,6-diaminoheptanedioate = meso- diaminoheptanedioate
Gene Name:: dapF
Uniprot ID:: P0A6K1
Molecular weight:: 30208

Reactions

LL-2,6-diaminoheptanedioate = meso-diaminoheptanedioate.

Protein Details

3. UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligase

General function:: Involved in ATP binding
Specific function:: Catalyzes the addition of meso-diaminopimelic acid to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanyl-D-glutamate (UMAG) in the biosynthesis of bacterial cell-wall peptidoglycan. Is also able to use many meso-diaminopimelate analogs as substrates, although much less efficiently, but not L-lysine
Gene Name:: murE
Uniprot ID:: P22188
Molecular weight:: 53343

Reactions

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-2,6-diaminoheptanedioate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate.

Transporters

Protein Details

1. Diaminopimelate epimerase

General function:: Involved in diaminopimelate epimerase activity
Specific function:: LL-2,6-diaminoheptanedioate = meso- diaminoheptanedioate
Gene Name:: dapF
Uniprot ID:: P0A6K1
Molecular weight:: 30208

Reactions

LL-2,6-diaminoheptanedioate = meso-diaminoheptanedioate.

Meso-2,6-Diaminoheptanedioate (ECMDB21665) (M2MDB002055)

Structure for #<Compound:0xa7e20c8c>

Enzymes

Reactions

Reactions

Reactions

Transporters

Reactions