(2S)-2-aminohexanedioic acid

• ChemBase ID: 110984
• Molecular Formular: C6H11NO4
• Molecular Mass: 161.15584
• Monoisotopic Mass: 161.06880784
• SMILES: N[C@@H](CCCC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)/t4-/m0/s1
• InChIKey: OYIFNHCXNCRBQI-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-aminohexanedioic acid
• IUPAC Traditional name: L-2-aminoadipic acid; aminoadipate
• Synonyms: H-2-Aad-OH; L-2-Aminoadipic acid; L-ORNITHINE MONO HCl; (S)-2-Aminohexanedioic acid; L-Homoglutamic acid; Aad; L-2-Aminoadipic acid; L-2-氨基己二酸

Database IDs

• CAS Number: 1118-90-7; 3184-13-2
• MDL Number: MFCD00002636
• Beilstein Number: 1724348
• PubChem SID: 162096525; 24278234
• PubChem CID: 92136

CALCULATED PROPERTIES

• Acid pKa: 2.0144308
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.8650444
• LogD (pH = 7.4): -5.627056
• Log P: -2.799617
• Molar Refractivity: 35.8887 cm^3
• Polarizability: 14.494345 Å^3
• Polar Surface Area: 100.62 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 203-205 °C (dec.); 203-205 °C (dec.)(lit.); ca 206°C dec.
• Optical Rotation: [α]20/D +25.0±0.5°, c = 5% in 6 M HCl; +25 (c=2 in 5N HCl)

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... GLUL(2752), LGSN(51557)rat ... Grm1(24414), Grm2(24415), Grm4(24417), Grm5(24418), Grm6(24419)

Product Information

• Purity: ≥97.0% (NT); ≥98% (TLC); 98%
• Linear Formula: HO2C(CH2)3CH(NH2)CO2H

DETAILS

MP Biomedicals - 05217320

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A7275

Biochem/physiol Actions
Glutamine synthetase inhibitor; gliotoxin.
包装
1, 5 g in poly bottle
100, 250 mg in poly bottle

Sigma Aldrich - 06653

Other Notes
Constituent of the Arnstein tripeptide, a precursor of the penicillins and cephalosporins 1,2; Chirally specific synthesis of (S)-(+)-cryptopleurine 3; In the synthesis of retrohydroxamate analogues of the microbial iron-transport agent ferrichrome 4