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

• ChemBase ID: 3251
• Molecular Formular: C7H14N2O4
• Molecular Mass: 190.19706
• Monoisotopic Mass: 190.09535694
• SMILES: N[C@@H](CCC[C@H](N)C(=O)O)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-/m0/s1
• InChIKey: GMKMEZVLHJARHF-WHFBIAKZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,6S)-2,6-diaminoheptanedioic acid
• IUPAC Traditional name: diamino-pimelic acid
• Synonyms: 2,6-Diaminopimelic Acid; rac.-DAP; DL-α,ε-Diaminopimelic acid; DL-2,6-Diaminoheptanedioic acid; DL-2,6-Diaminopimelic acid

Database IDs

• CAS Number: 2577-62-0
• MDL Number: MFCD09836080
• PubChem SID: 160966693; 46506904
• PubChem CID: 439283

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -4.13
• LOG S: -1.13
• Solubility (Water): 1.41e+01 g/l

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338

Product Information

• Purity: ≥95% (TLC)
• Empirical Formula (Hill Notation): C7H14N2O4

DETAILS

DrugBank - DB03590

Drug information: experimental

Sigma Aldrich - 92591

Analysis Note
diastereometric purity ≥99.0% (HPLC)
Biochem/physiol Actions
Stereoisomer of meso-DAP. meso-DAP is a biosynthetic precursor of the essential amino acid L-lysine1 and component of peptidoglycan in the cell wall of many bacteria2,3,4. As these functions are not observed in mammalian biochemistry, alpha,alpha′-diamino diacids (DADs) are of interest as potential antibiotics with low mammalian toxicity5.