LL-2,6-Diaminoheptanedioate (BioCAD00000013437)

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Metabolite Card

Formula: C7H14N2O4 (190.0954)
SMILES: N[C@@H](CCC[C@H](N)C(O)=O)C(O)=O

Synonyms [en]

LL-2,6-diaminoheptanedioate; LL-2,6-diaminopimelate; (2S,6S)-2,6-diaminoheptanedioic acid; 2,6-diamino-heptanedioic acid; LL-2,6-Diaminopimelic acid; 2,6-diaminopimelate

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

LL-2,6-Diaminoheptanedioate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000013437). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Diaminopimelic acid or DAPA is a lysine-like amino acid derivative that is a key component of the bacterial cell wall. DAPA is incorporated or integrated into peptidoglycan of gram negative bacteria and is the attachment point for Braun's lipoprotein (BLP or Murein Lipoprotein). BLP is found in gram-negative cell walls and is one of the most abundant membrane proteins. BLP is bound at its C-terminal end (a lysine) by a covalent bond to the peptidoglycan layer (specifically to diaminopimelic acid molecules) and is embedded in the outer membrane by its hydrophobic head (a cysteine with lipids attached). BLP tightly links the two layers and provides structural integrity to the bacterial outer membrane. Diaminopimelic acid can be found in human urine or feces due to the lysis or enzymatic breakdown of gram negative gut microbes.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 14289-34-0
  • CAS Registry Number: 583-93-7
  • CAS Registry Number: NA
  • PubChem: 1549100
  • PubChem: 439283
  • PubChem: 865
  • PubChem: 99290
  • ChEBI: ChEBI:16026
  • ChEBI: ChEBI:23673
  • ChEBI: ChEBI:57609
  • HMDB: HMDB0001370
  • LipidMaps: LMFA01170102
  • KEGG: C00666
  • BioCyc: CPD-20332
  • BioCyc: LL-DIAMINOPIMELATE
  • NCBI MeSH: Diaminopimelic Acid
  • Wikipedia: Diaminopimelic acid
  • Wikipedia: Diaminopimelic_acid
  • DrugBank: DB03590
  • RefMet: RM0136793
  • MoNA: BAF_UVA_POS001604
  • MoNA: BAF_UVA_POS001605
  • MoNA: BAF_UVA_POS001606
  • MoNA: BAF_UVA_POS001607
  • MoNA: BAF_UVA_POS001608
  • MoNA: EMBL-MCF_spec104284
  • MoNA: EMBL-MCF_spec105581
  • MoNA: EMBL-MCF_spec33330
  • MoNA: MoNA002307
  • MoNA: MoNA002308
  • MoNA: MoNA002309
  • MoNA: MoNA016757
  • MoNA: MoNA024146
  • MoNA: MoNA024180
  • MoNA: MoNA032633
  • MoNA: MoNA032634
  • MoNA: MoNA032635
  • MoNA: MoNA034761
  • MoNA: MoNA034765
  • MoNA: MoNA034767
  • MoNA: MoNA036445
  • MoNA: MoNA036449
  • MoNA: MoNA036450
  • MoNA: MoNA037383
  • MoNA: MoNA038135
  • MoNA: MoNA038706
  • MoNA: PR100128
  • MoNA: PR100129
  • MoNA: PR100543
  • MoNA: PS020301
  • MoNA: PS020302
  • MoNA: PS020303
  • MoNA: PS020304
  • MoNA: PS020305
  • Metlin: METLIN_45927

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02733 3.5.1.47 N6-acetyl-LL-2,6-diaminoheptanedioate amidohydrolase
KEGG:R02734 3.5.1.18 N-succinyl-LL-2,6-diaminoheptanedioate amidohydrolase
KEGG:R02735 5.1.1.7 LL-2,6-diaminoheptanedioate 2-epimerase
KEGG:R07613 2.6.1.83 LL-2,6-diaminoheptanedioate:2-oxoglutarate aminotransferase
BioCyc:RXN-7737 2.6.1.83 LL-DIAMINOPIMELATE + 2-KETOGLUTARATE<=>DELTA1-PIPERIDEINE-2-6-DICARBOXYLATE + GLT + WATER + PROTON
BioCyc:DIAMINOPIMEPIM-RXN 5.1.1.7 LL-DIAMINOPIMELATE --> MESO-DIAMINOPIMELATE
BioCyc:SUCCDIAMINOPIMDESUCC-RXN 3.5.1.18 WATER + N-SUCCINYLLL-2-6-DIAMINOPIMELATE --> LL-DIAMINOPIMELATE + SUC
BioCyc:N-ACETYLDIAMINOPIMELATE-DEACETYLASE-RXN 3.5.1.47 WATER + CPD-1771 --> LL-DIAMINOPIMELATE + ACET
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
BioCyc:TRYPANO_PWY0-781 aspartate superpathway
BioCyc:TRYPANO_PWY-724 superpathway of lysine, threonine and methionine biosynthesis II
BioCyc:TRYPANO_P4-PWY superpathway of lysine, threonine and methionine biosynthesis I
BioCyc:TRYPANO_DAPLYSINESYN-PWY lysine biosynthesis I
BioCyc:TRYPANO_PWY-5097 lysine biosynthesis VI
WikiPathways:WP5060 Peptidoglycan cytoplasmic synthesis and recycling pathways
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-OAU-2744343 Amino acid metabolism
Plant Reactome:R-OAU-1119273 Lysine biosynthesis I
Plant Reactome:R-OMI-5655122 Amino acid biosynthesis
Plant Reactome:R-OMI-1119419 Lysine biosynthesis VI
Plant Reactome:R-PDA-2744345 Metabolism and regulation
Plant Reactome:R-PDA-2744343 Amino acid metabolism
Plant Reactome:R-PDA-1119283 Lysine biosynthesis II
Plant Reactome:R-CCA-1119419 Lysine biosynthesis VI
Plant Reactome:R-EGR-1119283 Lysine biosynthesis II
Plant Reactome:R-JCU-1119419 Lysine biosynthesis VI
Plant Reactome:R-CSI-2744345 Metabolism and regulation
Plant Reactome:R-CSI-2744343 Amino acid metabolism
Plant Reactome:R-MDO-2744345 Metabolism and regulation
View All Pathways