2-[bis(phosphonomethyl)amino]acetic acid

• ChemBase ID: 152569
• Molecular Formular: C4H11NO8P2
• Molecular Mass: 263.079562
• Monoisotopic Mass: 262.99598958
• SMILES: C(C(=O)O)N(CP(=O)(O)O)CP(=O)(O)O
• Canonical SMILES: OC(=O)CN(CP(=O)(O)O)CP(=O)(O)O
• InChI: InChI=1S/C4H11NO8P2/c6-4(7)1-5(2-14(8,9)10)3-15(11,12)13/h1-3H2,(H,6,7)(H2,8,9,10)(H2,11,12,13)
• InChIKey: OXHDYFKENBXUEM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[bis(phosphonomethyl)amino]acetic acid
• IUPAC Traditional name: glyphosine
• Synonyms: Glyphosine; N-(Carboxymethyl)iminodi(methylphosphinic acid); N,N-Bis(phosphonomethyl)glycine; 增甘磷; N,N-双(膦羟甲基)甘氨酸

Database IDs

• CAS Number: 2439-99-8
• EC Number: 219-468-4
• MDL Number: MFCD00056670
• Beilstein Number: 1884944
• PubChem SID: 162246714
• PubChem CID: 17112

CALCULATED PROPERTIES

• Acid pKa: 1.2550385
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -8.450411
• LogD (pH = 7.4): -10.322514
• Log P: -2.5020306
• Molar Refractivity: 47.2261 cm^3
• Polarizability: 19.270777 Å^3
• Polar Surface Area: 155.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: MB9120000
• European Hazard Symbols: Irritant (Xi)
• UN Number: 3261
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 41
• Safety Statements: 26
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3261 8/PG 3

Product Information

• Purity: ≥98.0% (T)
• Empirical Formula (Hill Notation): C4H11NO8P2

DETAILS

Sigma Aldrich - 15149

Biochem/physiol Actions
Anti-diabetic; delay onset of diabetes in non-obese NOD mice1
Packaging
10, 50 g in poly bottle
Application
Application: Complexing agent; pK-values: pK1: ·2, pK2: 2.0, pK3: 5.20, pK4: 6.77, pK5: 10.89 Anti-diabetic; delay onset of diabetes in non-obese NOD miceGlyphosine binds to a pocket of MHC class II molecules I-Ag7 and DQ8, and modify T cell responses to the autoantigenic insulin B chain fragment 9-23 (B:9-23) peptide. Glyphosine stimulate IL-10 production and delay onset of diabetes in non-obese NOD mice.†