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

• ChemBase ID: 105218
• Molecular Formular: C27H30ClNO11
• Molecular Mass: 579.9802
• Monoisotopic Mass: 579.15073847
• SMILES: Cl.COc1cccc2c1C(=O)c1c(c(O)c3CC(O)(CC(OC4CC(N)C(O)C(C)O4)c3c1O)C(=O)CO)C2=O
• Canonical SMILES: OCC(=O)C1(O)CC(OC2CC(N)C(C(O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC.Cl
• InChI: InChI=1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)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;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H
• InChIKey: MWWSFMDVAYGXBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione hydrochloride
• IUPAC Traditional name: adriamycin hydrochloride
• Synonyms: Adriamycin; 14-Hydroxydaunomycin, HCl; DOXORUBICIN HYDROCHLORIDE; 4'-Epidoxorubicin; EPIRUBICIN HYDROCHLORIDE

Database IDs

• CAS Number: 56390-09-1; 25316-40-9
• EC Number: 260-145-2; 246-818-3
• PubChem SID: 162092068
• PubChem CID: 21584061

CALCULATED PROPERTIES

• Acid pKa: 9.53088
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -1.4428744
• LogD (pH = 7.4): -0.27556196
• Log P: 0.91642165
• Molar Refractivity: 134.5937 cm^3
• Polarizability: 52.692078 Å^3
• Polar Surface Area: 206.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 216°C (decomposes)

Safety Information

• Storage Condition: 2-8°C; Room Temperature (15-30°C)
• RTECS: QI9295750; QI9295900
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: R:22; R:45
• Safety Statements: S:28-36/37/39-45-53; S:36/37/39
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154

Product Information

• Purity: ≥95%; >95%

DETAILS

MP Biomedicals - 02195984

Hydrochloride
Purity: >95%
Anti-tumor antibiotic which is less toxic than doxorubicin.

MP Biomedicals - 02159101

Purity: >95%
by HPLC
Chemotherapeutic agent. Antitumor, immunosuppressive, and antibiotic agent. Blocks RNA polymerase and reverse transcriptase. Also inhibits nucleic acid synthesis.

REFERENCES

• McLoon, L.K., et al., Invest. Ophthamol. Vis. Sci., 32: 1667 (1991).
• Ellis, C.N., et al., Biochem. J., 245: 309 (1987).