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

• ChemBase ID: 168096
• Molecular Formular: C27H31NO11
• Molecular Mass: 545.53514
• Monoisotopic Mass: 545.18971082
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O[C@H]1O[C@H]([C@@H]([C@@H](C1)N)O)C)(C(CO)O)O)O)OC
• Canonical SMILES: OCC([C@@]1(O)C[C@H](O[C@@H]2C[C@@H](N)[C@H]([C@@H](O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC)O
• InChI: InChI=1S/C27H31NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15-17,22,29-31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,16?,17+,22-,27-/m0/s1
• InChIKey: NKZRZOVSJNSBFR-FIQSUXTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-10-{[(2S,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-(1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8S,10S)-10-{[(2S,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-(1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: Epirubicinol, 60% (Contains Unknown Salts)(Mixture of Diastereomers); 10-[(3-Amino-2,36,-trideoxy-α-L-arabino-hexopyranosyl)oxy]-8-[(1S)-1,2-dihydroxyethyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-(8S,10S)-5,12-naphthacenedione Citrate; 13-Dihydroadriamycin Citrate

Database IDs

• CAS Number: 76155-56-1
• PubChem SID: 162262228
• PubChem CID: 71316367

CALCULATED PROPERTIES

• Acid pKa: 9.7360735
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -2.0881715
• LogD (pH = 7.4): -1.0748831
• Log P: 0.22790514
• Molar Refractivity: 135.3604 cm^3
• Polarizability: 53.158913 Å^3
• Polar Surface Area: 209.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Dark Red Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E588655

A metabolite of Epirubicin, a neoplasm inhibitor.

REFERENCES

• Salvatorelli, E., et al.: J. Biol. Chem., 281, 10990 (2006)
• Salvatorelli, E., et al.: J. Pharmacol. Exper. Ther., 320, 790 (2006)
• Efferth, T., et al.: Clin. Cancer Res., 14, 2405 (2006)