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

• ChemBase ID: 171508
• Molecular Formular: C26H28ClNO9
• Molecular Mass: 533.95482
• Monoisotopic Mass: 533.14525916
• SMILES: c1cccc2c1C(=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.Cl
• Canonical SMILES: O[C@H]1[C@@H](N)C[C@@H](OC1C)O[C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2)C(=O)C.Cl
• InChI: InChI=1S/C26H27NO9.ClH/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31;/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3;1H/t10?,15-,16+,17+,21-,26+;/m1./s1
• InChIKey: JVHPTYWUBOQMBP-FRGYGULOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9S)-9-acetyl-7-{[(2R,4R,5S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione hydrochloride
• IUPAC Traditional name: (7S,9S)-9-acetyl-7-{[(2R,4R,5S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione hydrochloride
• Synonyms: (7S,9S)-9-Acetyl-7-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione Hydrochloride; 4-DMD HCl; 4-Demethoxydaunorubicin Hydrochloride; Idamycin; NSC 256439; Zavedos; Idarubicin Hydrochloride

Database IDs

• CAS Number: 57852-57-0
• PubChem SID: 164227418
• PubChem CID: 71749443

CALCULATED PROPERTIES

• Acid pKa: 9.54545
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.46867308
• LogD (pH = 7.4): 0.69595975
• Log P: 1.8979983
• Molar Refractivity: 126.4283 cm^3
• Polarizability: 49.47403 Å^3
• Polar Surface Area: 176.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Orange Solid
• Melting Point: 193-195°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I167000

Orally active anthracycline; analog of Daunorubicin. Antineoplastic.

REFERENCES

• Arcamone, F., et al.: Caner Treat. Rep., 60, 829 (1976)
• Zini, G., et al.: Cancer Chemother. Pharmacol., 16, 107 (1976)
• Gillies, H.C., et al.: Br.J. Clin. Pharmacol., 23, 303 (1976)
• Villani, F., et al.: Eur. J. Cancer Clin. Oncol., 25, 13 (1976)