(7S,9S)-9-amino-7-{[(2S,4R,5R)-4,5-dihydroxyoxan-2-yl]oxy}-6,11-dihydroxy-9-[1-hydroxy(1-13C)ethyl]-5,7,8,9,10,12-hexahydro(4a,12a-13C2)tetracene-5,12-dione

• ChemBase ID: 160601
• Molecular Formular: C25H27NO9
• Molecular Mass: 488.46114451
• Monoisotopic Mass: 488.17864596
• SMILES: c1ccc[13c]2[13c]1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O[C@@H]1OC[C@@H](O)[C@H](C1)O)([13CH](O)C)N)O
• Canonical SMILES: O[C@@H]1CO[C@H](C[C@@H]1O)O[C@H]1C[C@@](N)(Cc2c1c(O)c1c(c2O)C(=O)[13c]2[13c](C1=O)cccc2)[13CH](O)C
• InChI: InChI=1S/C25H27NO9/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31/h2-5,10,14-17,27-29,32-33H,6-9,26H2,1H3/t10?,14-,15-,16+,17+,25+/m1/s1/i10+1,11+1,12+1
• InChIKey: HSDGDISMODBEAN-XMRNVHSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9S)-9-amino-7-{[(2S,4R,5R)-4,5-dihydroxyoxan-2-yl]oxy}-6,11-dihydroxy-9-[1-hydroxy(1-^1^3C)ethyl]-5,7,8,9,10,12-hexahydro(4a,12a-^1^3C₂)tetracene-5,12-dione
• IUPAC Traditional name: (7S,9S)-9-amino-7-{[(2S,4R,5R)-4,5-dihydroxyoxan-2-yl]oxy}-6,11-dihydroxy-9-[1-hydroxy(1-^1^3C)ethyl]-8,10-dihydro(4a,12a-^1^3C₂)-7H-tetracene-5,12-dione
• Synonyms: (7S,9S)-9-Amino-7-[(2-deoxy-β-D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxy-9-(1-hydroxyethyl)-5,12-naphthacenedione-13C3; 13-Hydroxy SM 5887-13C3; Amrubicinol-13C3 (Mixture of Diastereomers)

Database IDs

• PubChem SID: 162254736
• PubChem CID: 71313395

CALCULATED PROPERTIES

• Acid pKa: 9.58018
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -1.1697867
• LogD (pH = 7.4): 0.2634604
• Log P: 1.3452663
• Molar Refractivity: 122.9347 cm^3
• Polarizability: 48.112732 Å^3
• Polar Surface Area: 179.77 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A635213

A labelled metabolite of Amrubicin, which is active and possesses a cytotoxicity 10 to 100 times that of the parent drug.

REFERENCES

• Oken, M., et al.: Am. J. Clin. Oncol., 5, 649 (1982)
• Ohara, H., et al.: Biochem. Pharmacol., 50, 221 (1982)
• de Jongh, F., et al.: J. Clin. Oncol., 19, 3733 (1982)
• Backstrom, G., et al.: Eur. J. Pharm. Sci., 18, 359 (1982)