4-(2-amino-1H-imidazol-5-yl)-2,3-dibromo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-8-one

• ChemBase ID: 171472
• Molecular Formular: C11H11Br2N5O
• Molecular Mass: 389.04594
• Monoisotopic Mass: 386.933034
• SMILES: c1(c2c([nH]c1Br)C(=O)NCCC2c1cnc([nH]1)N)Br
• Canonical SMILES: O=C1NCCC(c2c1[nH]c(c2Br)Br)c1cnc([nH]1)N
• InChI: InChI=1S/C11H11Br2N5O/c12-7-6-4(5-3-16-11(14)17-5)1-2-15-10(19)8(6)18-9(7)13/h3-4,18H,1-2H2,(H,15,19)(H3,14,16,17)
• InChIKey: MRMGABUTBNWSLA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-amino-1H-imidazol-5-yl)-2,3-dibromo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-8-one
• IUPAC Traditional name: 4-(2-amino-3H-imidazol-4-yl)-2,3-dibromo-1H,4H,5H,6H,7H-pyrrolo[2,3-c]azepin-8-one
• Synonyms: 4-(2-Amino-1H-imidazol-5-yl)-2,3-dibromo-4,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8(1H)-one; (+/-)-Hymenine; (+/-)-Hymenin

Database IDs

• CAS Number: 154569-13-8
• PubChem SID: 164227382
• PubChem CID: 9930243

CALCULATED PROPERTIES

• Acid pKa: 9.862875
• H Acceptors: 3
• H Donor: 4
• LogD (pH = 5.5): -0.30328774
• LogD (pH = 7.4): -0.20849225
• Log P: 0.4373259
• Molar Refractivity: 79.3342 cm^3
• Polarizability: 29.288137 Å^3
• Polar Surface Area: 99.59 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H998030

A marine sponge alkaloid, 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)