Bafilomycin

Bafilomycin A1
IUPAC name (3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16- [(1S,2R,3S)-3-[(2R,4R,5S,6R)-2,4-dihydroxy-6- isopropyl-5-methyl-2-tetrahydropyranyl]-2- hydroxy-1-methylbutyl]-8-hydroxy-3,15- dimethoxy-5,7,9,11-tetramethyl-1- oxacyclohexadeca-3,5,11,13-tetraen-2-one
Identifiers
CAS number	88899-55-2 N
PubChem	6436223
ChemSpider	10251049 Y
DrugBank	DB06733
ChEMBL	CHEMBL290814 N
Jmol-3D images	Image 1 Image 2
SMILES C[C@H]1C/C(=C/C=C/[C@@H]([C@H](OC(=O)/C(=C/C(=C/[C@H]([C@H]1O)C)/C)/OC)[C@@H](C)[C@H]([C@H](C)[C@]2(C[C@H]([C@@H]([C@H](O2)C(C)C)C)O)O)O)OC)/C O[C@@]1(C[C@@H](O)[C@H](C)[C@H](O1)C(C)C)[C@@H](C)[C@H](O)[C@H](C)[C@H]2OC(=O)C(\OC)=C\C(\C)=C\[C@@H](C)[C@@H](O)[C@H](C)CC(\C)=C\C=C\[C@@H]2OC
InChI InChI=1S/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12+,20-13+,21-16+,29-17-/t22-,23-,24+,25+,26+,27-,28+,30+,31-,32-,33-,35-/m1/s1 Y Key: XDHNQDDQEHDUTM-XJKSCTEHSA-N Y InChI=1/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12+,20-13+,21-16+,29-17-/t22-,23-,24+,25+,26+,27-,28+,30+,31-,32-,33-,35-/m1/s1 Key: XDHNQDDQEHDUTM-XJKSCTEHBD
Properties
Molecular formula	C35H58O9
Molar mass	622.83 g/mol
Appearance	Yellow powder
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

The bafilomycins are a family of toxic macrolide antibiotic derived from Streptomyces griseus. These compounds all appear in the same fermentation and have quite similar biological activity. Bafilomycins are specific inhibitors of vacuolar-type H+-ATPase.

The most used bafilomycin is bafilomycin A1. This is a useful tool as it can prevent the re-acidification of synaptic vesicles once they have undergone exocytosis.

Bafilomycin has antibacterial, antifungal, antineoplastic, immunosuppressive activities.In addition, bafilomycin A1 has antimalarial activity It has been shown to decrease multi-drug resistance.

Bafilomycin B1 has been mentioned as a potential antiosteoporotic agent in treating bone lytic diseases.