(2S)-2-amino-6-diazo-5-oxohexanoic acid

• ChemBase ID: 103179
• Molecular Formular: C6H9N3O3
• Molecular Mass: 171.15396
• Monoisotopic Mass: 171.06439116
• SMILES: N[C@@H](CCC(=O)C=[N+]=[N-])C(=O)O
• Canonical SMILES: [N-]=[N+]=CC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H,11,12)/t5-/m0/s1
• InChIKey: YCWQAMGASJSUIP-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-6-diazo-5-oxohexanoic acid
• IUPAC Traditional name: 6-diazo-5-oxo-L-norleucine; DON
• Synonyms: 6-Diazo-5-oxo-L-norleucine; DON; (S)-2-Amino-6-diazo-5-oxocaproic acid; 6-DIAZO-5-OXO-L-NORLEUCINE

Database IDs

• CAS Number: 157-03-9
• MDL Number: MFCD00037218
• Beilstein Number: 1725815
• PubChem SID: 162090629; 24893639
• PubChem CID: 5359375

CALCULATED PROPERTIES

• Acid pKa: 1.8687847
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -4.262169
• LogD (pH = 7.4): -4.2932534
• Log P: -4.2198367
• Molar Refractivity: 38.3951 cm^3
• Polarizability: 15.334695 Å^3
• Polar Surface Area: 97.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: light yellow crystalline
• Melting Point: 145-155°C (dec.)

Safety Information

• Storage Condition: 0°C
• RTECS: RC6340000
• European Hazard Symbols: Toxic (T); Irritant (Xi)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25; R:36/37/38
• Safety Statements: 36/37/39-45; S:20-25-26-37/39
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

DETAILS

MP Biomedicals - 02150845

Light yellow crystals. Exhibits teratogenic effects, anti-microbial action, enzymatic inhibition.

Sigma Aldrich - D2141

Biochem/physiol Actions
DON is used to study mechanisms of glutamine utilizing enzymes such as carbamoyl phosphate synthase and cytidine triphosphate synthase.

REFERENCES

• King, G.L., et al., J. Biol. Chem. , 253 : 3933 (1978).
• Morgan, P.R. and Pratt, R.M., Teratology , 15 , 281 (1977).