2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-10-{[(5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

• ChemBase ID: 175078
• Molecular Formular: C36H62N2O11
• Molecular Mass: 698.88428
• Monoisotopic Mass: 698.43536081
• SMILES: O1C(=O)C[C@H]([C@@H]([C@H]([C@H](C[C@H]([C@H](/C=C/C=C/C[C@H]1C)OC1CC[C@@H]([C@H](O1)C)N(C)C)C)CC=O)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C)O)N(C)C)O)OC)O
• Canonical SMILES: O=CC[C@H]1C[C@@H](C)[C@H](/C=C/C=C/C[C@H](OC(=O)C[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](C)[C@H]([C@H]([C@H]1O)N(C)C)O)OC)O)C)OC1CC[C@@H]([C@H](O1)C)N(C)C
• InChI: InChI=1S/C36H62N2O11/c1-21-19-25(17-18-39)34(49-36-33(43)31(38(7)8)32(42)24(4)47-36)35(44-9)27(40)20-29(41)45-22(2)13-11-10-12-14-28(21)48-30-16-15-26(37(5)6)23(3)46-30/h10-12,14,18,21-28,30-36,40,42-43H,13,15-17,19-20H2,1-9H3/b11-10+,14-12+/t21-,22-,23-,24-,25+,26+,27-,28+,30?,31+,32-,33-,34+,35+,36+/m1/s1
• InChIKey: SUBWVHAACKTENX-POIPKBAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-10-{[(5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
• IUPAC Traditional name: 2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-10-{[(5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
• Synonyms: 4A-O-De(2,6-dideoxy-3-C-methyl-α-L-ribo-hexopyranosyl)-9-O-[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]leucomycin V; Neo Spiramycin I

Database IDs

• CAS Number: 70253-62-2
• PubChem SID: 164230988
• PubChem CID: 71750991

CALCULATED PROPERTIES

• Acid pKa: 12.615331
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): -3.6758707
• LogD (pH = 7.4): -0.46665612
• Log P: 2.0388243
• Molar Refractivity: 185.2487 cm^3
• Polarizability: 73.652504 Å^3
• Polar Surface Area: 156.69 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Cloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 111-116°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N390040

The major metabolite of Spiramycin I in meat, fish, and milk.

REFERENCES

• Nakazawa, S., et al.: J. Antibiot., 20, 259 (1967)
• Rubinstein, E., et al.: J. Antimicrob. Chemother., 42, 572 (1967)
• Rourick, R., et al.: J. Pharm. Biomed. Anal., 14, 1743 (1967)