2-amino-1-N,9-N-bis[(2S,3R)-3-hydroxy-1-oxobutan-2-yl]-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide dideuterium

• ChemBase ID: 165349
• Molecular Formular: C24H26N4O8
• Molecular Mass: 498.48524
• Monoisotopic Mass: 498.17506381
• SMILES: c12c(c(ccc1C)C(=O)N[C@@H]([C@@H](C)O)C=O)nc1c(o2)c(c(=O)c(c1C(=O)N[C@@H]([C@@H](C)O)C=O)N)C
• Canonical SMILES: O=C[C@H]([C@H](O)C)NC(=O)c1ccc(c2c1nc1c(o2)c(C)c(=O)c(c1C(=O)N[C@@H]([C@H](O)C)C=O)N)C
• InChI: InChI=1S/C24H26N4O8/c1-9-5-6-13(23(34)26-14(7-29)11(3)31)18-21(9)36-22-10(2)20(33)17(25)16(19(22)28-18)24(35)27-15(8-30)12(4)32/h5-8,11-12,14-15,31-32H,25H2,1-4H3,(H,26,34)(H,27,35)/t11-,12-,14-,15-/m1/s1
• InChIKey: DOQZSDAWXRCISW-QHSBEEBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-1-N,9-N-bis[(2S,3R)-3-hydroxy-1-oxobutan-2-yl]-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide dideuterium
• IUPAC Traditional name: 2-amino-1-N,9-N-bis[(2S,3R)-3-hydroxy-1-oxobutan-2-yl]-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboxamide dideuterium
• Synonyms: Actinomycin D; Actactinomycin A IV; Actinomycin 7; Dilactone Actinomycindioic D Acid; Lyovac Cosmegen; Cosmogen; Meractinomycin; Dactinomycin

Database IDs

• CAS Number: 50-76-0
• PubChem SID: 162259482
• PubChem CID: 71315162

CALCULATED PROPERTIES

• Acid pKa: 11.728196
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.3033944
• LogD (pH = 7.4): -1.3034111
• Log P: -1.303393
• Molar Refractivity: 130.9664 cm^3
• Polarizability: 47.830112 Å^3
• Polar Surface Area: 197.48 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Red Solid
• Melting Point: 245-247°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D102500

Antibiotic substance belonging to the actinomycin complex, produced by several Streptomyces spp. Antineoplastic.

REFERENCES

• Manaker, et al.: Antibiot. Ann., 55, 853 (1954)
• Jain, S., et al.: J. Mol. Biol., 114, 317 (1954)
• Nakajima, K., et al.: Pept. Chem., 19, 143 (1954)
• Shereda, R., et al.: J. Biol. Chem., 282, 19247 (1954)