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

• ChemBase ID: 174651
• 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]1N2)OC)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]1N2)OC
• InChI: InChI=1S/C16H19N3O6/c1-6-11(20)10-9(12(21)13(6)23-2)7(5-25-15(17)22)16(24-3)14-8(18-14)4-19(10)16/h7-8,14,18H,4-5H2,1-3H3,(H2,17,22)/t7-,8+,14+,16-/m1/s1
• InChIKey: HYFMSAFINFJTFH-NGSRAFSJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4S,6S,7R,8S)-7,11-dimethoxy-12-methyl-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)-7,11-dimethoxy-12-methyl-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)-8-[[(Aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione; Mitomycin A

Database IDs

• CAS Number: 4055-39-4
• PubChem SID: 164230561
• PubChem CID: 19972

CALCULATED PROPERTIES

• Acid pKa: -0.061832182
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -2.2186708
• LogD (pH = 7.4): -2.4677725
• Log P: -2.2068343
• Molar Refractivity: 86.3626 cm^3
• Polarizability: 33.066914 Å^3
• Polar Surface Area: 130.1 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Benzene; Chloroform; Methanol
• Apperance: Red-Violet Solid
• Melting Point: 159-161°C (dec)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M371890

The 6-methoxy analog of Mitomycin C. An antitumor antibiotic.

REFERENCES

• Kinoshita, S., et al.: J. Med. Chem., 14, 13 (1971)
• Kishi, Y., et al.: J. Nat. Prod., 42, 549 (1971)