[(4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

• ChemBase ID: 176837
• Molecular Formular: C16H20N4O5
• Molecular Mass: 348.3538
• Monoisotopic Mass: 348.14336976
• SMILES: C1(=C(C(=O)C2=C(C1=O)[C@H]([C@@]1(N2C[C@H]2[C@@H]1N2C)OC)COC(=O)N)C)N
• Canonical SMILES: CO[C@@]12[C@@H]3[C@@H](N3C)CN2C2=C([C@H]1COC(=O)N)C(=O)C(=C(C2=O)C)N
• InChI: InChI=1S/C16H20N4O5/c1-6-10(17)13(22)9-7(5-25-15(18)23)16(24-3)14-8(19(14)2)4-20(16)11(9)12(6)21/h7-8,14H,4-5,17H2,1-3H3,(H2,18,23)/t7-,8+,14+,16-,19?/m1/s1
• InChIKey: HRHKSTOGXBBQCB-VFWICMBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^2,^7.0^4,^6]trideca-1(9),11-dien-8-yl]methyl carbamate
• IUPAC Traditional name: [(4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^2,^7.0^4,^6]trideca-1(9),11-dien-8-yl]methyl carbamate
• Synonyms: (1aS,8S,8aR,8bS)-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione; ENT 50825; Methyl Mitomycin C; Methylmitomycin; N-Methylmitomycin C; NCI 56410; NSC 56410; Porfiromycine; Regamycin; U 14743; Porfiromycin

Database IDs

• CAS Number: 801-52-5
• PubChem SID: 164232747
• PubChem CID: 13116

CALCULATED PROPERTIES

• Acid pKa: -0.30243385
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -2.915903
• LogD (pH = 7.4): -2.9312284
• Log P: -2.807146
• Molar Refractivity: 88.5636 cm^3
• Polarizability: 33.481956 Å^3
• Polar Surface Area: 127.96 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P689450

Antibiotic substance isolated from a Streptomyces ardus fermentation broth. Antibacterial; antineoplastic.

REFERENCES

• Tannock, I., et al.: Clin. Cancer Res., 8, 878 (2002)
• Cummings, J., et al.: Br. J. Cancer, 92, 532 (2002)
• Ivascu, A., et al.: J. Biomol. Screen, 11, 922 (2002)