(3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-14-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione

• ChemBase ID: 175834
• Molecular Formular: C35H61NO12
• Molecular Mass: 687.85834
• Monoisotopic Mass: 687.4193764
• SMILES: [C@H]1([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@H](C[C@]2(C1=O)CO2)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)O)C)O[C@@H]1O[C@@H]([C@@H]([C@H](C1)OC)O)C)C)C)C)O)C
• Canonical SMILES: CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@H](C(=O)[C@@]3(C[C@@H]([C@@H]([C@H]2C)O[C@@H]2O[C@H](C)C[C@H]([C@H]2O)N(C)C)C)CO3)C)O[C@@H]([C@@H]1O)C
• InChI: InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+/m0/s1
• InChIKey: RZPAKFUAFGMUPI-QESOVKLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-14-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione
• IUPAC Traditional name: oleandomycin
• Synonyms: 8-(3,5-Dihydroxy-2,4-dimethylhexanoyl)-5-(4-dimethylaminotetrahydro-3-hydroxy-6-methylpyran-2-yloxy)-8,9-epoxy-2,4,6-trimethyl-3-(tetrahydro-5-hydroxy-4-methoxy-6-methylpyran-2-yloxy)nonanoic Acid μ-Lactone; Amimycin; Antibiotic PA 105; Landomycin; Oleandomycin A; PA 105; PA 775; Romicil; Oleandomycin

Database IDs

• CAS Number: 3922-90-5
• PubChem SID: 164231744
• PubChem CID: 72493

CALCULATED PROPERTIES

• Acid pKa: 12.673328
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): 0.18664895
• LogD (pH = 7.4): 1.952015
• Log P: 2.9751384
• Molar Refractivity: 173.6925 cm^3
• Polarizability: 70.79451 Å^3
• Polar Surface Area: 165.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O517500

Antibiotic substance produced by Streptomyces antibioticus no. ATCC 11891. Antibacterial.

REFERENCES

• Sous, H., et al.: Arzneim.-Forsch., 8, 386 (1958)
• Hahn, et al.: Antibiotics, 1, 378 (1958)