[(4S,6S,7R,8R)-11-amino-7-hydroxy-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: 174653
• Molecular Formular: C15H18N4O5
• Molecular Mass: 334.32722
• Monoisotopic Mass: 334.1277197
• 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)N
• Canonical SMILES: NC(=O)OC[C@H]1C2=C(N3[C@]1(O)[C@@H]1[C@@H](N1C)C3)C(=O)C(=C(C2=O)N)C
• InChI: InChI=1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23)13-7(18(13)2)3-19(15)10(8)11(5)20/h6-7,13,23H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7-,13-,15+,18?/m0/s1
• InChIKey: JHIATKDBEBOOCO-HSBXUTMMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4S,6S,7R,8R)-11-amino-7-hydroxy-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)-11-amino-7-hydroxy-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)-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-hydroxy-1,5-dimethylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione; Mitomycin D

Database IDs

• CAS Number: 10169-34-3
• PubChem SID: 164230563
• PubChem CID: 15572005

CALCULATED PROPERTIES

• Acid pKa: -0.2504838
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -3.560048
• LogD (pH = 7.4): -3.574374
• Log P: -3.4343855
• Molar Refractivity: 83.8124 cm^3
• Polarizability: 31.591412 Å^3
• Polar Surface Area: 138.96 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M371905

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)