8-acetyl-10-[(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: 103163
• Molecular Formular: C27H30ClNO10
• Molecular Mass: 563.9808
• Monoisotopic Mass: 563.15582385
• SMILES: Cl.COc1cccc2c1C(=O)c1c(O)c3c(CC(O)(CC3OC3CC(N)C(O)C(C)O3)C(=O)C)c(O)c1C2=O
• Canonical SMILES: COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)C(OC1CC(N)C(C(O1)C)O)CC(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
• InChIKey: GUGHGUXZJWAIAS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-acetyl-10-[(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: daunomycin hydrochloride
• Synonyms: Daunorubicin hydrochloride; Daunorubicine hydrochloride; Leukaemomycin C; DAUNOMYCIN HYDROCHLORIDE

Database IDs

• CAS Number: 23451-50-6
• EC Number: 245-723-4
• PubChem SID: 162090626
• PubChem CID: 21864425

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

PROPERTIES

Physical Property

• Melting Point: 188-190°C

Safety Information

• Storage Condition: 2-8°C
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: R:25
• Safety Statements: S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154

DETAILS

MP Biomedicals - 02150777

From Streptomyces peucetius
Hydrochloride
LD₅₀ in mice 26 mg/kg in vitro .
An antineoplastic of Rhodomycin group.

REFERENCES

• Di Marco, et al., Cancer Chemother. Rep. , 53 : 33 (1969).