(7S)-7-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,11-dihydroxy-9-(2-hydroxyacetyl)-4-methoxy-5,7,8,12-tetrahydrotetracene-5,12-dione

• ChemBase ID: 160661
• Molecular Formular: C27H27NO10
• Molecular Mass: 525.50398
• Monoisotopic Mass: 525.16349607
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C=C(C[C@@H]2O[C@H]1O[C@H]([C@H]([C@@H](C1)N)O)C)C(=O)CO)O)OC
• Canonical SMILES: OCC(=O)C1=Cc2c([C@H](C1)O[C@@H]1C[C@@H](N)[C@@H]([C@@H](O1)C)O)c(O)c1c(c2O)C(=O)c2c(C1=O)c(OC)ccc2
• InChI: InChI=1S/C27H27NO10/c1-10-23(31)14(28)8-18(37-10)38-17-7-11(15(30)9-29)6-13-20(17)27(35)22-21(25(13)33)24(32)12-4-3-5-16(36-2)19(12)26(22)34/h3-6,10,14,17-18,23,29,31,33,35H,7-9,28H2,1-2H3/t10-,14-,17-,18+,23+/m0/s1
• InChIKey: GNZRKCZTDXRJOT-LQNHAXQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S)-7-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,11-dihydroxy-9-(2-hydroxyacetyl)-4-methoxy-5,7,8,12-tetrahydrotetracene-5,12-dione
• IUPAC Traditional name: (10S)-10-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,11-dihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydrotetracene-5,12-dione
• Synonyms: (S)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-9,10-dihydro-6,11-dihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione; 9,10-Anhydro Doxorubicin

Database IDs

• CAS Number: 80996-23-2
• PubChem SID: 162254796
• PubChem CID: 71313415

CALCULATED PROPERTIES

• Rotatable Bonds: 5
• Lipinski's Rule of Five: false
• LogD (pH = 7.4): 0.65675175
• Log P: 1.7764994
• Molar Refractivity: 133.9592 cm^3
• Polarizability: 51.84686 Å^3
• Polar Surface Area: 185.84 Å^2
• Acid pKa: 9.449598
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -0.5285572

DETAILS

Toronto Research Chemicals - A638300

Doxorubicin (D558000) analog as antitumor agent.

REFERENCES

• Potti, G., et al.: J. Med. Chem., 25, 478 (1982)