Daunorubicin hydrochloride, Anthracycline antibiotic

Key facts

CAS number

23541-50-6

Purity

>95%

Form

Solid

form

Molecular weight

564 Da

Molecular formula

C₂₇H₂₉NO₁₀.HCl

PubChem

62770

Nature

Synthetic

Solubility

Soluble in water to 50 mM

Biochemical name

Daunorubicin hydrochloride

Biological description

Anthracycline antibiotic. DNA and RNA synthesis inhibitor. Reduces tau mRNA levels. Induces DNA fragmentation and apoptosis. Antiproliferative and cytotoxic effects in vivo. Orally active.

Canonical smiles

CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O.Cl

Isomeric smiles

C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O.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-QQYBVWGSSA-N

IUPAC Name

(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride