2-amino-5-{8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-4-ylidene}-4,5-dihydro-1H-imidazol-4-one

• ChemBase ID: 165486
• Molecular Formular: C11H11N5O2
• Molecular Mass: 245.23734
• Monoisotopic Mass: 245.09127462
• SMILES: c1c2c([nH]c1)C(=O)NCC/C/2=C/1\C(=O)N=C(N1)N
• Canonical SMILES: NC1=NC(=O)/C(=C/2\CCNC(=O)c3c2cc[nH]3)/N1
• InChI: InChI=1S/C11H11N5O2/c12-11-15-8(10(18)16-11)6-2-4-14-9(17)7-5(6)1-3-13-7/h1,3,13H,2,4H2,(H,14,17)(H3,12,15,16,18)/b8-6-
• InChIKey: JYRJOQGKGMHTOO-VURMDHGXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-5-{8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-4-ylidene}-4,5-dihydro-1H-imidazol-4-one
• IUPAC Traditional name: 2-amino-5-{8-oxo-1H,5H,6H,7H-pyrrolo[2,3-c]azepin-4-ylidene}-1H-imidazol-4-one
• Synonyms: (4Z)-4-(2-Amino-1,5-dihydro-5-oxo-4H-imidazol-4-ylidene)-4,5,6,7-tetrahydro-pyrrolo[2,3-c]azepin-8(1H)-one; (Z)-2-Debromohymenialdisine; (Z)-Debromohymenialdisine; SKF 108753; Debromo Hymenialdisine

Database IDs

• CAS Number: 75593-17-8
• PubChem SID: 162259619
• PubChem CID: 5288032

CALCULATED PROPERTIES

• Acid pKa: 13.252343
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.6941377
• LogD (pH = 7.4): -1.6936163
• Log P: -1.6936091
• Molar Refractivity: 64.8685 cm^3
• Polarizability: 23.454145 Å^3
• Polar Surface Area: 112.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: >250°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D208900

An antineoplastic agent, a protein kinase inhibitor isolated from Marine Organisms, Terrestrial Plants, and Microorganisms. A natural product.

REFERENCES

• Bailey, D., et al.: J. Med. Chem., 16, 1300 (1973)
• Kitagawa, I., et al.: Chem. Pharm. Bull., 31, 2321 (1973)
• Schmitz, F., et al.: J. Nat. Prod., 48, 47 (1973)
• Kobayashi, J., et al.: Experientia, 44, 86 (1973)