2-(4-carbamimidoylphenyl)-1H-indole-6-carboximidamide

• ChemBase ID: 126866
• Molecular Formular: C16H15N5
• Molecular Mass: 277.3238
• Monoisotopic Mass: 277.13274551
• SMILES: N=C(N)c1ccc(c2cc3ccc(cc3[nH]2)C(=N)N)cc1
• Canonical SMILES: NC(=N)c1ccc(cc1)c1cc2c([nH]1)cc(cc2)C(=N)N
• InChI: InChI=1S/C16H15N5/c17-15(18)10-3-1-9(2-4-10)13-7-11-5-6-12(16(19)20)8-14(11)21-13/h1-8,21H,(H3,17,18)(H3,19,20)
• InChIKey: FWBHETKCLVMNFS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-carbamimidoylphenyl)-1H-indole-6-carboximidamide
• IUPAC Traditional name: DAPI
• Synonyms: DAPI; DAPI; 2-(4-Amidinophenyl)-6-indolecarbamidine, Dihydrochloride; 2-[4-(Aminoiminomethyl)phenyl]-1H-indole-6-carboximidamide Hydrochloride; 4',6-Diamidino-2-phenylindole Dihydrochloride; 4',6-Diamidino-2-phenylindole Dihydrochloride

Database IDs

• CAS Number: 28718-90-3
• PubChem SID: 162221193
• PubChem CID: 2954
• CHEBI ID: 51231
• CHEMBL: 48217
• Chemspider ID: 2848
• Wikipedia Title: DAPI

CALCULATED PROPERTIES

• Acid pKa: 14.501453
• H Acceptors: 4
• H Donor: 5
• LogD (pH = 5.5): -3.3503847
• LogD (pH = 7.4): -3.3225315
• Log P: 1.4801712
• Molar Refractivity: 105.5032 cm^3
• Polarizability: 33.95792 Å^3
• Polar Surface Area: 115.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Yellow Solid
• Melting Point: >300°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D416050

A cell-permeable DNA-binding dye. Binds preferentially to DNA rich in adenine and thymine. Used in flow cytometry for measuring nuclear DNA content or for sorting isolated chromosomes.

REFERENCES

• Jpeeesen, C, and Nielsen, P.E.: Eur. J. Biochem., 182, 437 (1989)
• Li,J., et al.: J. Exp. Biol., 200, 1499 (1989)
• Zaitsev, E.N., and Kowalczykowsi, S.C.: Nucl. Acids Res., 26(1989)
• 650 (1989)
• Germ, M., et al.: Biochem. Biophys. Res. Commun., 261, 452 (19