(7S,9S)-7-{[(2R,4S,5R)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy}-9-(1,2-dihydroxyethyl)-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 160721
• Molecular Formular: C26H27IO11
• Molecular Mass: 642.39045
• Monoisotopic Mass: 642.05980968
• SMILES: c1cccc2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O[C@@H]1OC([C@@H]([C@H](C1I)O)O)C)(C(CO)O)O)O
• Canonical SMILES: OCC([C@@]1(O)C[C@H](O[C@@H]2OC(C)[C@@H]([C@H](C2I)O)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2)O
• InChI: InChI=1S/C26H27IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13-14,18-19,24-25,28-30,33-36H,6-8H2,1H3/t9?,13-,14?,18?,19-,24+,25-,26-/m0/s1
• InChIKey: HDWHFQYNYXMYTJ-PPUCWGMASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9S)-7-{[(2R,4S,5R)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy}-9-(1,2-dihydroxyethyl)-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (7S,9S)-7-{[(2R,4S,5R)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy}-9-(1,2-dihydroxyethyl)-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: 6-(4-Methoxyphenyl)-3(2H)-pyridazinone; 6-(p-Methoxyphenyl)-3(2H)-pyridazinone; p-Anisylpyridazone

Database IDs

• CAS Number: 2166-33-8
• PubChem SID: 162254856
• PubChem CID: 71313446

CALCULATED PROPERTIES

• Acid pKa: 9.460742
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): 2.032319
• LogD (pH = 7.4): 2.0286343
• Log P: 2.0323663
• Molar Refractivity: 140.0082 cm^3
• Polarizability: 54.8856 Å^3
• Polar Surface Area: 194.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White to Yellow Solid

DETAILS

Toronto Research Chemicals - A674050

An Intermediate for the synthesis of the drug Gabazine, as well as several analgesic pharmaceuticals.

REFERENCES

• Pitarch, L., et al.: Eur. J. Med. Chem., 9, 644 (1974)
• Sumakanth, M., et al.: J. Pharm. Res., 6, 166 (1974)