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

• ChemBase ID: 162809
• Molecular Formular: C28H30BrNO12
• Molecular Mass: 652.4413
• Monoisotopic Mass: 651.09513741
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O[C@@H]1O[C@H]([C@@H](O)[C@@H](C1)N)C)(C(=O)CBr)O)O)OC.C(=O)O
• Canonical SMILES: BrCC(=O)[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.OC=O
• InChI: InChI=1S/C27H28BrNO10.CH2O2/c1-10-22(31)13(29)6-17(38-10)39-15-8-27(36,16(30)9-28)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;2-1-3/h3-5,10,13,15,17,22,31,33,35-36H,6-9,29H2,1-2H3;1H,(H,2,3)/t10-,13-,15-,17-,22+,27-;/m0./s1
• InChIKey: USWDRBNCRQVMDU-RUELKSSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-(2-bromoacetyl)-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione; formic acid
• IUPAC Traditional name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-(2-bromoacetyl)-6,8,11-trihydroxy-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione; formic acid
• Synonyms: (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-(2-bromoacetyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Formate; 14-Bromodaunomycin Formate Salt; 14-Bromo Daunorubicin Formate Salt

Database IDs

• PubChem SID: 162256944
• PubChem CID: 71314232

CALCULATED PROPERTIES

• Acid pKa: 9.530921
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 0.097212404
• LogD (pH = 7.4): 1.2645245
• Log P: 2.456525
• Molar Refractivity: 140.6282 cm^3
• Polarizability: 54.829075 Å^3
• Polar Surface Area: 185.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Red Solid
• Melting Point: 167-170°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - B682790

Adriamycin analogue; use as anticancer agent.

REFERENCES

• Krishan, A., et al.: Cancer Res., 41, 2745 (1981)
• Mueller, M., et al.: Eur. J. Biochem., 140, 447 (1981)