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

• ChemBase ID: 126943
• Molecular Formular: C7H14N2O4
• Molecular Mass: 190.19706
• Monoisotopic Mass: 190.09535694
• SMILES: O=C(O)[C@@H](N)CCC[C@@H](N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CCC[C@H](C(=O)O)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+
• InChIKey: GMKMEZVLHJARHF-SYDPRGILSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,6S)-2,6-diaminoheptanedioic acid
• IUPAC Traditional name: diaminopimelic acid
• Synonyms: Diaminopimelic acid; (2SR, 6RS)-2,6-Diaminoheptanedioic acid; meso-2,6-Diaminopimelic acid

Database IDs

• CAS Number: 583-93-7; 922-54-3
• MDL Number: MFCD09836095
• Beilstein Number: 1726899
• PubChem SID: 162221269
• PubChem CID: 1549101; 99290
• CHEBI ID: 16488
• CHEMBL: 415306
• Chemspider ID: 89700
• MeSH Name: Diaminopimelic+acid
• Wikipedia Title: Diaminopimelic_acid

CALCULATED PROPERTIES

• Acid pKa: 1.847075
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.5455008
• LogD (pH = 7.4): -5.5511074
• Log P: -5.545368
• Molar Refractivity: 43.6394 cm^3
• Polarizability: 17.83188 Å^3
• Polar Surface Area: 126.64 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white powder
• Melting Point: 295°C
• Boiling Point: 426.7°C
• Density: 1.344 g/mL

Safety Information

• German water hazard class: 3
• Main Hazard: Irritant

Product Information

• Purity: ≥98% (TLC)
• Empirical Formula (Hill Notation): C7H14N2O4

DETAILS

Sigma Aldrich - 07036

Biochem/physiol Actions
Penultimate biosynthetic precursor of the essential amino acid L-lysine.1 Component of peptidoglycan in the cell wall of many bacteria.2,3,4