[(2S)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-1H,2H,3H,5H,8H-cyclohexa[b]pyrrolizin-9-yl]methyl carbamate

• ChemBase ID: 170452
• Molecular Formular: C14H16N4O5
• Molecular Mass: 320.30064
• Monoisotopic Mass: 320.11206963
• SMILES: C1(=C(C(=O)c2c(C1=O)c(c1n2C[C@@H](C1O)N)COC(=O)N)C)N
• Canonical SMILES: NC(=O)OCc1c2C(O)[C@H](Cn2c2c1C(=O)C(=C(C2=O)C)N)N
• InChI: InChI=1S/C14H16N4O5/c1-4-8(16)13(21)7-5(3-23-14(17)22)9-12(20)6(15)2-18(9)10(7)11(4)19/h6,12,20H,2-3,15-16H2,1H3,(H2,17,22)/t6-,12?/m0/s1
• InChIKey: XNHZZRIKMUCTHU-RLWMBFFFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-1H,2H,3H,5H,8H-cyclohexa[b]pyrrolizin-9-yl]methyl carbamate
• IUPAC Traditional name: [(2S)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-1H,2H,3H-cyclohexa[b]pyrrolizin-9-yl]methyl carbamate
• Synonyms: (2S)-2,7-Diamino-9-[[(aminocarbonyl)oxy]methyl]-2,3-dihydro-1-hydroxy-6-methyl-1H-pyrrolo[1,2-a]indole-5,8-dione; 1-Hydroxy-2,7-diamino Mitosene(Mixture cis/trans)

Database IDs

• CAS Number: 1192552-64-9
• PubChem SID: 164226362
• PubChem CID: 13817091

CALCULATED PROPERTIES

• Acid pKa: 13.335219
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.0258694
• LogD (pH = 7.4): -3.384942
• Log P: -2.398502
• Molar Refractivity: 80.3569 cm^3
• Polarizability: 30.118248 Å^3
• Polar Surface Area: 163.66 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H939700

Mitomycin (M371900) impurity.

REFERENCES

• Siegel, D., et al.: Biochemistry, 31, 7879 (1992)
• Kontou, M., et al.: Oncogene, 21, 2406 (1992)