[(3S,4S,7R,8S,9R)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,6-diazapentacyclo[7.4.0.01,6.02,4.03,7]tridec-11-en-8-yl]methyl carbamate

• ChemBase ID: 159624
• Molecular Formular: C15H18N4O5
• Molecular Mass: 334.32722
• Monoisotopic Mass: 334.1277197
• SMILES: C1(=C(C(=O)C23[C@H](C1=O)[C@H]([C@@]1(N2C[C@@H]2[C@H]1N32)OC)COC(=O)N)C)N
• Canonical SMILES: CO[C@@]12[C@H]3[C@@H]4N3C3(N2C4)[C@@H]([C@H]1COC(=O)N)C(=O)C(=C(C3=O)C)N
• InChI: InChI=1S/C15H18N4O5/c1-5-9(16)10(20)8-6(4-24-13(17)22)15(23-2)11-7-3-18(15)14(8,12(5)21)19(7)11/h6-8,11H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,8+,11+,14?,15-,19?/m1/s1
• InChIKey: ZOVLGAUVYBEUSN-ZWSGUIOPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3S,4S,7R,8S,9R)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,6-diazapentacyclo[7.4.0.0^1,^6.0^2,^4.0^3,^7]tridec-11-en-8-yl]methyl carbamate
• IUPAC Traditional name: [(3S,4S,7R,8S,9R)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,6-diazapentacyclo[7.4.0.0^1,^6.0^2,^4.0^3,^7]tridec-11-en-8-yl]methyl carbamate
• Synonyms: (1S,2S,4S,5R,6S,6aR,10aS,11S)-8-Amino-6-[[(aminocarbonyl)oxy]methyl]-2,3,6,6a-tetrahydro-5-methoxy-9-methyl-1,2,5-metheno-1H,5H-imidazo[2,1-i]indole-7,10-dione; Antibiotic CX 1; [1S-(1α,2α,4β,5β,6α,6aα,10aR*,11R*)]-8-amino-6-[[(aminocarbonyl)oxy]methyl]-2,3,6,6a-tetrahydro-5-methoxy-9-methyl-1,2,5-Metheno-1H,5H-imidazo[2,1-i]indole-7,10-dione; Albomitomycin CDISCONTINUED

Database IDs

• CAS Number: 111750-67-5
• PubChem SID: 162253759
• PubChem CID: 71313066

CALCULATED PROPERTIES

• Acid pKa: 12.764458
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.05868707
• LogD (pH = 7.4): -0.058680356
• Log P: -0.058678403
• Molar Refractivity: 80.3629 cm^3
• Polarizability: 31.569384 Å^3
• Polar Surface Area: 127.96 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A513500

A derivative of of the antitumor compound Mitomycin C (M371900).

REFERENCES

• Lang, W. et al.: Anal. Biochem., 343, 268 (2005)
• Fiallo, M.M. et al.: J. Med. Chem., 46, 1683 (2005)
• Kono, M. et al.: J. Antibiot., 48, 1683 (2005)