meso-2,6-diaminopimelic acid (CHEBI:16488)

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CHEBI:16488 - meso-2,6-diaminopimelic acid

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ChEBI Name	meso-2,6-diaminopimelic acid

ChEBI ID	CHEBI:16488

ChEBI ASCII Name	meso-2,6-diaminopimelic acid

Definition	The meso-isomer of 2,6-diaminopimelic acid. It is a key constituent of bacterial peptidoglycan and is often found in human urine due to the breakdown of the gut microbes.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40838, CHEBI:10598, CHEBI:25204

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

Molfile

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27 26 0 0 0 0 999 V2000

-0.3430 -0.1310 3.7390 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2390 0.5110 2.5070 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.3570 -0.1430 1.2590 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2340 0.5090 0.0080 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.3620 -0.1440 -1.2390 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2290 0.5070 -2.4890 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.3580 -0.1360 -3.7180 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1970 -1.0930 4.2310 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.4620 0.3640 4.2890 O 0 0 0 0 0 0 0 0 0 0 0 0

0.1790 -1.0990 -4.2120 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.4800 0.3580 -4.2640 O 0 0 0 0 0 0 0 0 0 0 0 0

1.6970 0.3310 2.5040 N 0 0 0 0 0 0 0 0 0 0 0 0

1.6870 0.3280 -2.4920 N 0 0 0 0 0 0 0 0 0 0 0 0

0.0040 1.5750 2.5060 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1220 -1.2070 1.2590 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4390 -0.0090 1.2610 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0000 1.5730 0.0080 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3160 0.3760 0.0060 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1270 -1.2090 -1.2380 H 0 0 0 0 0 0 0 0 0 0 0 0

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-1.8570 -0.0540 -5.0530 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8670 -0.6630 2.5040 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0310 0.6820 1.6180 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8560 -0.6660 -2.4920 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0200 0.6780 -3.3780 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 8 2 0 0 0 0

1 9 1 0 0 0 0

2 3 1 0 0 0 0

2 12 1 0 0 0 0

2 14 1 0 0 0 0

3 4 1 0 0 0 0

3 15 1 0 0 0 0

3 16 1 0 0 0 0

4 5 1 0 0 0 0

4 17 1 0 0 0 0

4 18 1 0 0 0 0

5 6 1 0 0 0 0

5 19 1 0 0 0 0

5 20 1 0 0 0 0

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9 22 1 0 0 0 0

11 23 1 0 0 0 0

12 24 1 0 0 0 0

12 25 1 0 0 0 0

13 26 1 0 0 0 0

13 27 1 0 0 0 0

M END): 17 ms

reading 27 atoms

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1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

27 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile expand

Wikipedia	License
Diaminopimelic acid (DAP) is an amino acid, representing an epsilon-carboxy derivative of lysine. meso-α,ε-Diaminopimelic acid is the last intermediate in the biosynthesis of lysine and undergoes decarboxylation by diaminopimelate decarboxylase to give the final product. DAP is a characteristic of certain cell walls of some bacteria. DAP is often found in the peptide linkages of NAM-NAG chains that make up the cell wall of gram-negative bacteria. When provided, they exhibit normal growth. When in deficiency, they still grow but with the inability to make new cell wall peptidoglycan. This is also the attachment point for Braun's lipoprotein.
Read full article at Wikipedia

Formulae

C7H14N2O4
C7H14N2O4

Net Charge

Average Mass

190.199

Monoisotopic Mass

190.09536

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+

InChIKey

GMKMEZVLHJARHF-SYDPRGILSA-N

SMILES

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

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. (via 2,6-diaminopimelic acid )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	meso-2,6-diaminopimelic acid (CHEBI:16488) has role human metabolite (CHEBI:77746) meso-2,6-diaminopimelic acid (CHEBI:16488) is a 2,6-diaminopimelic acid (CHEBI:23673) meso-2,6-diaminopimelic acid (CHEBI:16488) is conjugate acid of meso-2,6-diaminopimelate(2−) (CHEBI:30308) meso-2,6-diaminopimelic acid (CHEBI:16488) is tautomer of meso-2,6-diaminopimelic acid dizwitterion (CHEBI:57791)

Incoming	(2R,6S)-2,6-diamino-3ξ-hydroxyheptanedioic acid (CHEBI:144634) has functional parent meso-2,6-diaminopimelic acid (CHEBI:16488) meso-2,6-diaminopimelate(2−) (CHEBI:30308) is conjugate base of meso-2,6-diaminopimelic acid (CHEBI:16488) meso-2,6-diaminopimelic acid dizwitterion (CHEBI:57791) is tautomer of meso-2,6-diaminopimelic acid (CHEBI:16488)

IUPAC Name

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

Synonyms	Sources
meso-2,6-Diaminopimelic acid	KEGG COMPOUND
meso-diaminoheptanedioic acid	ChEBI

Manual Xrefs	Databases
API	PDBeChem
C00007595	KNApSAcK
C00680	KEGG COMPOUND
Diaminopimelic_acid	Wikipedia
View more database links

Registry Numbers	Types	Sources
8218693	Reaxys Registry Number	Reaxys
922-54-3	CAS Registry Number	ChemIDplus

Citations

Last Modified

07 March 2023

CHEBI:16488 - meso-2,6-diaminopimelic acid

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