(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-[(1R)-1-hydroxyethyl]-1-(13C,2H3)methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 165429
• Molecular Formular: C27H31NO10
• Molecular Mass: 530.52839484
• Monoisotopic Mass: 530.19815104
• 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@@H](C)O)O)O)O[13CH3]
• Canonical SMILES: [13CH3]Oc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1C[C@@H](N)[C@@H]([C@@H](O1)C)O)C[C@](C2)(O)[C@H](O)C
• InChI: InChI=1S/C27H31NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10-11,14,16-17,22,29-30,32,34-35H,7-9,28H2,1-3H3/t10-,11+,14-,16-,17-,22+,27-/m0/s1/i3+1
• InChIKey: HJEZFVLKJYFNQW-MQCRQUTRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-[(1R)-1-hydroxyethyl]-1-(^1^3C,^2H₃)methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-[(1R)-1-hydroxyethyl]-1-(^1^3C,^2H₃)methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• Synonyms: (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-[1-hydroxyethyl]-1-(methoxy-13C,d3)-5,12-naphthacenedione; 13-Dihydrodaunorubicin-13C,d3; Duborimycin-13C,d3; Leukaemomycin D-13C,d3; Daunorubicinol-13C,d3 (mixture of diastereomers)

Database IDs

• PubChem SID: 162259562
• PubChem CID: 71315195

CALCULATED PROPERTIES

• Acid pKa: 9.736299
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -1.0412652
• LogD (pH = 7.4): -0.02799974
• Log P: 1.2748721
• Molar Refractivity: 133.8167 cm^3
• Polarizability: 52.4915 Å^3
• Polar Surface Area: 189.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Dark Red Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D194512

A metabolite of Daunorubicin. Used as an antineoplastic. Complexes with DNA. Inhibits DNA and RNA synthesis.

REFERENCES

• Mizuno, N.S., et al.: Cancer Res., 35, 1542 (1975)
• Munger, C., et al.: Cancer Res., 48, 2404 (1975)
• Kobayashi, Y., et al.: J. Biol. Chem., 275, 17639 ( 2000), Burke, B., et al.: Cardiovasc. Toxicol., 2, 41 (1975)