4-[4-(2-carbamimidamidoacetamido)-1-methyl-1H-pyrrole-2-amido]-N-(2-carbamimidoylethyl)-1-methyl-1H-pyrrole-3-carboxamide dihydrochloride

• ChemBase ID: 132510
• Molecular Formular: C18H28Cl2N10O3
• Molecular Mass: 503.38612
• Monoisotopic Mass: 502.17229017
• SMILES: Cn1cc(c(c1)NC(=O)c1cc(cn1C)NC(=O)CNC(=N)N)C(=O)NCCC(=N)N.Cl.Cl
• Canonical SMILES: NC(=N)CCNC(=O)c1cn(cc1NC(=O)c1cc(cn1C)NC(=O)CNC(=N)N)C.Cl.Cl
• InChI: InChI=1S/C18H26N10O3.2ClH/c1-27-8-11(16(30)23-4-3-14(19)20)12(9-27)26-17(31)13-5-10(7-28(13)2)25-15(29)6-24-18(21)22;;/h5,7-9H,3-4,6H2,1-2H3,(H3,19,20)(H,23,30)(H,25,29)(H,26,31)(H4,21,22,24);2*1H
• InChIKey: AGIFDNIQJFEFMQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(2-carbamimidamidoacetamido)-1-methyl-1H-pyrrole-2-amido]-N-(2-carbamimidoylethyl)-1-methyl-1H-pyrrole-3-carboxamide dihydrochloride
• IUPAC Traditional name: 4-[4-(2-carbamimidamidoacetamido)-1-methylpyrrole-2-amido]-N-(2-carbamimidoylethyl)-1-methylpyrrole-3-carboxamide dihydrochloride
• Synonyms: Congocidin; Sinanomycin; Netropsin dihydrochloride

Database IDs

• CAS Number: 1438-30-8
• MDL Number: MFCD00144883
• PubChem SID: 24897909; 162226787
• PubChem CID: 16219788

CALCULATED PROPERTIES

• Acid pKa: 12.063171
• H Acceptors: 8
• H Donor: 8
• LogD (pH = 5.5): -6.5564013
• LogD (pH = 7.4): -6.5367055
• Log P: -2.4698253
• Molar Refractivity: 138.8927 cm^3
• Polarizability: 41.97236 Å^3
• Polar Surface Area: 208.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 mg/mL
• Apperance: faint yellow powder

Safety Information

• RTECS: DW2973000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC and TLC)
• Biological Source: from Streptomyces netropsis

DETAILS

Sigma Aldrich - N9653

Caution
Protect from light.
Biochem/physiol Actions
Netropsin is an unusual n-methylpyrrole-containing oligopeptide that binds to AT-rich sequences of dsDNA, especially in the minor groove. Thus, it protects such regions from DNase I and other endonucleases, and also inhibits topoisomerases. Netropsin disrupts the cell cycle, prolonging G and arresting in G.