(8S,10S)-8-acetyl-10-{[(2R,4R,5S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 163819
• Molecular Formular: C26H27NO10
• Molecular Mass: 513.49328
• Monoisotopic Mass: 513.16349607
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O[C@@H]1OC([C@@H](O)[C@H](C1)N)C)(C(=O)C)O)O)O
• Canonical SMILES: N[C@H]1C[C@@H](OC([C@H]1O)C)O[C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)c(O)ccc2)C(=O)C
• InChI: InChI=1S/C26H27NO10/c1-9-21(30)13(27)6-16(36-9)37-15-8-26(35,10(2)28)7-12-18(15)25(34)20-19(23(12)32)22(31)11-4-3-5-14(29)17(11)24(20)33/h3-5,9,13,15-16,21,29-30,32,34-35H,6-8,27H2,1-2H3/t9?,13-,15+,16+,21-,26+/m1/s1
• InChIKey: XREUEWVEMYWFFA-XQPIDWLJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-8-acetyl-10-{[(2R,4R,5S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8S,10S)-8-acetyl-10-{[(2R,4R,5S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: Carminomicin; NSC 180024; Carminomycin

Database IDs

• CAS Number: 39472-31-6
• PubChem SID: 162257954
• PubChem CID: 71314566

CALCULATED PROPERTIES

• Acid pKa: 8.801489
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -0.1141801
• LogD (pH = 7.4): 1.0787874
• Log P: 2.1299548
• Molar Refractivity: 128.4092 cm^3
• Polarizability: 50.12665 Å^3
• Polar Surface Area: 196.84 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Dark Red to Black Solid
• Melting Point: 191-192°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C183650

An antitumor antibiotic.

REFERENCES

• Fiallo, M., et al.: Biochem. Pharm., 45, 659 (1993)
• Huang, P., et al.: Curr. Opin. Genet. Dev., 11, 104 (1993)
• Pae, H., et al.: Leukemia Res., 25, 339 (1993)