1,3-bis(4-amino-2-methylquinolin-6-yl)urea hydrate

• ChemBase ID: 154748
• Molecular Formular: C21H22N6O2
• Molecular Mass: 390.43838
• Monoisotopic Mass: 390.18042397
• SMILES: Cc1cc(c2cc(ccc2n1)NC(=O)Nc1ccc2c(c1)c(cc(n2)C)N)N.O
• Canonical SMILES: O=C(Nc1ccc2c(c1)c(N)cc(n2)C)Nc1ccc2c(c1)c(N)cc(n2)C.O
• InChI: InChI=1S/C21H20N6O.H2O/c1-11-7-17(22)15-9-13(3-5-19(15)24-11)26-21(28)27-14-4-6-20-16(10-14)18(23)8-12(2)25-20;/h3-10H,1-2H3,(H2,22,24)(H2,23,25)(H2,26,27,28);1H2
• InChIKey: UXYZYUHSZVKWTR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-bis(4-amino-2-methylquinolin-6-yl)urea hydrate
• IUPAC Traditional name: aminoquinuride dihydrochloride hydrate
• Synonyms: 1,3-Bis(4-amino-2-methyl-6-quinolyl)urea hydrate; Aminokinuride; Aminoquincarbamide; Aminoquinuride; N,N′-Bis(4-amino-2-methyl-6-quinolyl)urea; NSC 12155; Surfen hydrate; (bis-2-methyl-4-amino-quinolyl-6-carbamide hydrate; Aminoquinuride

Database IDs

• MDL Number: MFCD17215963
• PubChem SID: 162248886
• PubChem CID: 71311959

CALCULATED PROPERTIES

• Acid pKa: 11.518541
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.5478865
• LogD (pH = 7.4): -0.4782081
• Log P: 2.038853
• Molar Refractivity: 112.4792 cm^3
• Polarizability: 43.13769 Å^3
• Polar Surface Area: 118.95 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: light tan to yellow powder

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H20N6O · xH2O

DETAILS

Sigma Aldrich - S6951

Biochem/physiol Actions
Surfen is a heparan sulfate antagonist, originally developed in the late thirties as an excipient for the production of depot insulin. Heparan sulfate (HS) is structurally related to heparin but contains fewer sulfate groups per disaccharide, and it exists almost exclusively attached to protein cores of proteoglycans, which cells either display on the plasma membrane or secrete into the extracellular matrix. Surfen binds to the chains of glycosaminoglycan (GAG)/HS and prevents binding of the enzymes and proteins thus act as HS antagonist. Surfen is more potent than protamine, a clinically used heparin antagonist.