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

• ChemBase编号: 3251
• 分子式: C7H14N2O4
• 平均质量: 190.19706
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S,6S)-2,6-diaminoheptanedioic acid
• IUPAC传统名: diamino-pimelic acid
• 别名: 2,6-Diaminopimelic Acid; rac.-DAP; DL-α,ε-Diaminopimelic acid; DL-2,6-Diaminoheptanedioic acid; DL-2,6-Diaminopimelic acid

登记号

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

理论计算性质

JChem

• Acid pKa: 1.847075
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): -5.5455008
• LogD (pH = 7.4): -5.5511074
• Log P: -5.545368
• 摩尔折射率: 43.6394 cm^3
• 极化性: 17.83188 Å^3
• 极化表面积: 126.64 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -4.13
• LOG S: -1.13
• 溶解度: 1.41e+01 g/l

分子性质

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36/37
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338

产品相关信息

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

详细说明

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.