{[2-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)ethoxy]methyl}phosphonic acid hydrate

• ChemBase ID: 154682
• Molecular Formular: C8H14N5O6P
• Molecular Mass: 307.200421
• Monoisotopic Mass: 307.06816982
• SMILES: c1nc2c(=O)[nH]c(nc2n1CCOCP(=O)(O)O)N.O
• Canonical SMILES: Nc1[nH]c(=O)c2c(n1)n(CCOCP(=O)(O)O)cn2.O
• InChI: InChI=1S/C8H12N5O5P.H2O/c9-8-11-6-5(7(14)12-8)10-3-13(6)1-2-18-4-19(15,16)17;/h3H,1-2,4H2,(H2,15,16,17)(H3,9,11,12,14);1H2
• InChIKey: BDVQXHFCXJXVND-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[2-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)ethoxy]methyl}phosphonic acid hydrate
• IUPAC Traditional name: [2-(2-amino-6-oxo-1H-purin-9-yl)ethoxy]methylphosphonic acid hydrate
• Synonyms: 9-[2-(Phosphonomethoxy)ethyl]guanine hydrate; PMEG hydrate

Database IDs

• MDL Number: MFCD19443863
• PubChem SID: 162248820
• PubChem CID: 71311936

CALCULATED PROPERTIES

• Acid pKa: 1.1517628
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.6113367
• LogD (pH = 7.4): -4.770491
• Log P: -2.3463173
• Molar Refractivity: 64.5417 cm^3
• Polarizability: 23.718493 Å^3
• Polar Surface Area: 152.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Toxic (T)
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C8H12N5O5P · xH2O

DETAILS

Sigma Aldrich - M2199

Biochem/physiol Actions
The acyclic nucleotide 9-(2-phosphonylmethoxyethyl)guanine (PMEG) forms an active phosphorylated metabolite, PMEG diphosphate (PMEGpp), in cells and causes cytotoxicity in dividing cells due to potent inhibition of the nuclear DNA polymerases resulting in inhibition of DNA synthesis and/or DNA repair.