sodium (2S,4R,6E,8S)-8-[(2S,5R,7R,8R,9S)-9-hydroxy-2-[(2R,4S,5S,7R,9S,10R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-9-{[(5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy}-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,4,6-trimethyl-5-oxonon-6-enoate

• ChemBase ID: 72683
• Molecular Formular: C47H77NaO14
• Molecular Mass: 889.09565
• Monoisotopic Mass: 888.52110143
• SMILES: O([Na])C(=O)[C@H](C[C@@H](C)C(=O)/C(=C/[C@@H]([C@H]1O[C@]2(C[C@@H]([C@H]1C)O)CC[C@](O2)([C@@H]1O[C@]2([C@@H]([C@H](C1)OC1O[C@@H]([C@H](CC1)OC)C)C)[C@H](C[C@@H](O2)[C@H]1O[C@]([C@@H](C[C@@H]1C)C)(CO)O)C)C)C)/C)C
• Canonical SMILES: [Na]OC(=O)[C@H](C[C@H](C(=O)/C(=C/[C@@H]([C@H]1O[C@@]2(CC[C@@](O2)(C)[C@H]2C[C@H](OC3CC[C@@H]([C@H](O3)C)OC)[C@H]([C@]3(O2)O[C@H](C[C@@H]3C)[C@H]2O[C@@](O)(CO)[C@@H](C[C@@H]2C)C)C)C[C@@H]([C@H]1C)O)C)/C)C)C
• InChI: InChI=1S/C47H78O14.Na/c1-24(40(50)25(2)18-28(5)43(51)52)17-26(3)41-31(8)34(49)22-45(59-41)16-15-44(11,61-45)38-21-36(56-39-14-13-35(54-12)33(10)55-39)32(9)47(58-38)30(7)20-37(57-47)42-27(4)19-29(6)46(53,23-48)60-42;/h17,25-39,41-42,48-49,53H,13-16,18-23H2,1-12H3,(H,51,52);/q;+1/p-1/b24-17+;/t25-,26+,27+,28+,29-,30+,31-,32-,33-,34+,35+,36+,37-,38-,39?,41-,42+,44+,45-,46+,47+;/m1./s1
• InChIKey: XMAIRYYXDCNFKP-DYTQFKGPSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,4R,6E,8S)-8-[(2S,5R,7R,8R,9S)-9-hydroxy-2-[(2R,4S,5S,7R,9S,10R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-9-{[(5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy}-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,4,6-trimethyl-5-oxonon-6-enoate
• IUPAC Traditional name: sodium (2S,4R,6E,8S)-8-[(2S,5R,7R,8R,9S)-9-hydroxy-2-[(2R,4S,5S,7R,9S,10R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-9-{[(5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy}-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,4,6-trimethyl-5-oxonon-6-enoate
• Synonyms: Nanchangmycin

Database IDs

• CAS Number: 65101-87-3
• PubChem SID: 162037604
• PubChem CID: 46930988

CALCULATED PROPERTIES

• Acid pKa: 11.107247
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): 7.524499
• LogD (pH = 7.4): 7.524415
• Log P: 7.5245
• Molar Refractivity: 224.4615 cm^3
• Polarizability: 92.68145 Å^3
• Polar Surface Area: 177.9 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1450

Research Area

• Description: Infection

Biological Activity

• Description: Nanchangmycin (dianemycin) is a polyether antibiotic with similar structure to dianemycin and is very active against a broad spectrum of harmful nematodes and insects but not for for mammals and plants.
• In Vitro: Nanchangmycin inhibits gram-positive bacteria. ^[1]
• In Vivo: Nanchangmycin can be used as a growth promotant in poultry and to cure coccidiosis in chickens. ^[1]
• Features: Nanchangmycin produced by Streptomyces nanchangensis NS3226 is a polyether antibiotic.

References

• References: [1] Liu T, et al. Chem Biol. 2008, 15(5), 449-458.

REFERENCES

• Liu T, et al. Chem Biol. 2008, 15(5), 449-458.