[(4S,6S,7R,8R)-7-hydroxy-11-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: 174652
• Molecular Formular: C16H19N3O6
• Molecular Mass: 349.33856
• Monoisotopic Mass: 349.12738534
• SMILES: C1(=C(C(=O)C2=C(C1=O)[C@@H]([C@@]1(N2C[C@H]2[C@@H]1N2C)O)COC(=O)N)C)OC
• Canonical SMILES: COC1=C(C)C(=O)C2=C(C1=O)[C@H](COC(=O)N)[C@@]1(N2C[C@H]2[C@@H]1N2C)O
• InChI: InChI=1S/C16H19N3O6/c1-6-11(20)10-9(12(21)13(6)24-3)7(5-25-15(17)22)16(23)14-8(18(14)2)4-19(10)16/h7-8,14,23H,4-5H2,1-3H3,(H2,17,22)/t7-,8-,14-,16+,18?/m0/s1
• InChIKey: UZUUQCBCWDBYCG-DQRAMIIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4S,6S,7R,8R)-7-hydroxy-11-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,8R)-7-hydroxy-11-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,8R,8aR,8bS)-8-[[(Aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-hydroxy-6-methoxy-1,5-dimethylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione; Mitomycin B

Database IDs

• CAS Number: 4055-40-7
• PubChem SID: 164230562
• PubChem CID: 19973

CALCULATED PROPERTIES

• Acid pKa: -0.00525076
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -2.8123846
• LogD (pH = 7.4): -2.8243992
• Log P: -2.6953056
• Molar Refractivity: 86.9061 cm^3
• Polarizability: 32.99912 Å^3
• Polar Surface Area: 122.17 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M371895

An antitumor antibiotic. It is used as antineoplastic.

REFERENCES

• Kinoshita, S., et al.: J. Med. Chem., 14, 13 (1971)
• Beijnen, J.H., et al.: Anal. Profiles Drug Subs., 16, 361 (1971)