(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yloxy]oxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 176785
• Molecular Formular: C32H37NO12
• Molecular Mass: 627.63568
• Monoisotopic Mass: 627.23157563
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O[C@H]1C[C@H]([C@@H]([C@@H](O1)C)O[C@@H]1CCCCO1)N)(C(=O)CO)O)O)OC
• Canonical SMILES: OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@@H](N)[C@@H]([C@@H](O2)C)O[C@@H]2CCCCO2)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
• InChI: InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1
• InChIKey: KMSKQZKKOZQFFG-YXRRJAAWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yloxy]oxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yloxy]oxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: (8S,10S)-10-[[3-Amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione; Pinorubicin; Therarubicin; Pirarubicin

Database IDs

• CAS Number: 72496-41-4
• PubChem SID: 164232695
• PubChem CID: 11296583

CALCULATED PROPERTIES

• Acid pKa: 9.478123
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): 0.1203337
• LogD (pH = 7.4): 1.3603758
• Log P: 2.5154042
• Molar Refractivity: 157.3784 cm^3
• Polarizability: 61.92432 Å^3
• Polar Surface Area: 204.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate,; Methanol
• Apperance: Red Solid
• Melting Point: >170°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - P501500

Structural analog of Doxorubicin. Antineoplastic.

REFERENCES

• Umezawa, H., et al.: J. Antibiot., 32, 1082 (1979)
• Majima, H., et al.: Biomed. Pharmacother., 41, 237 (1979)
• Miller, A.A., et al.: Cancer Res., 47, 1461 (1979)
• Fallik, D., et al.: Ann. Ocol., 14, 856 (1979)