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

• ChemBase ID: 165426
• Molecular Formular: C27H30ClNO10
• Molecular Mass: 563.9808
• Monoisotopic Mass: 563.15582385
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)c(c2c(c1O)C[C@@](C[C@@H]2O[C@H]1C[C@H]([C@H]([C@@H](O1)C)O)N)(O)C(=O)C)O)OC.Cl
• Canonical SMILES: COc1cccc2c1C(=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(=O)C.Cl
• InChI: InChI=1S/C27H29NO10.ClH/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;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22-,27-;/m0./s1
• InChIKey: GUGHGUXZJWAIAS-RBSGUPIDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-8-acetyl-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione hydrochloride
• IUPAC Traditional name: (8S,10S)-8-acetyl-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione hydrochloride
• Synonyms: (8S,10S)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Hydrochloride; (8S-cis)-4'-Epidaunorubicin Hydrochloride; 4'-epi-Daunomycin Hydrochloride; NSC 249333; 4'-epi-Daunorubicin Hydrochloride

Database IDs

• CAS Number: 56390-08-0
• PubChem SID: 162259559
• PubChem CID: 12309102

CALCULATED PROPERTIES

• Acid pKa: 9.530939
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -0.6256268
• LogD (pH = 7.4): 0.54168487
• Log P: 1.7336931
• Molar Refractivity: 132.8915 cm^3
• Polarizability: 52.022972 Å^3
• Polar Surface Area: 185.84 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D194490

Daunorubicin (D194500) impurity. Daunomycin analog antitumor.

REFERENCES

• Cassinelli, G., et al.: J. Antib., 38, 856 (1985)
• Arcamone, F., et al.: J. Med. Chem.,18, 703 (1985)