Paldimycin (U-70138F)

Class: Paulomycin

Spectrum of activity:	Gram-negative
Details of activity:	Protein synthesis inhibitor. Good activity against Gram-positiives, excellent activity against MRS and MSSA (1)
Combined with other compounds:	mixture of U-67963 and U-67964 derived from paulomycins A and B
Institute where first reported:	Upjohn Company (Pfizer, USA)
Year first mentioned:	1986
Development status:	Inactive
Reason Dropped:	With prolonged exposure to paldimycin at subinhibitory and inhibitory concentrations, there is an increase of resistant isolates of MRS (1). It's activity is pH dependent (2)

Chemical structure(s):
Canonical SMILES:	CC[C@H](C)C(=O)O[C@@H](C)C1(C(C)OC(CC1OC)OC2C(C([C@]3(CC(=O)C(=N)C(=C3O)C(=O)O)O)OC(COC(=O)C)C2OC(=O)C(C(C)SC[C@@H](C(=O)O)NC(=O)C)NC(=S)SC[C@@H](C(=O)O)NC(=O)C)O)O.CC(C)C(=O)O[C@@H](C)C1(C(C)OC(CC1OC)OC2C(C([C@]3(CC(=O)C(=N)C(=C3O)C(=O)O)O)OC(COC(=O)C)C2OC(=O)C(C(C)SC[C@@H](C(=O)O)NC(=O)C)NC(=S)SC[C@@H](C(=O)O)NC(=O)C)O)O
Isomeric SMILES:	CC[C@H](C)C(=O)O[C@@H](C)C1(C(OC(CC1OC)OC2C(C(OC(C2OC(=O)C(C(C)SC[C@@H](C(=O)O)NC(=O)C)NC(=S)SC[C@@H](C(=O)O)NC(=O)C)COC(=O)C)[C@]3(CC(=O)C(=N)C(=C3O)C(=O)O)O)O)C)O.CC1C(C(CC(O1)OC2C(C(OC(C2OC(=O)C(C(C)SC[C@@H](C(=O)O)NC(=O)C)NC(=S)SC[C@@H](C(=O)O)NC(=O)C)COC(=O)C)[C@]3(CC(=O)C(=N)C(=C3O)C(=O)O)O)O)OC)([C@H](C)OC(=O)C(C)C)O
InChI:	InChI=1S/C44H64N4O23S3.C43H62N4O23S3/c1-10-16(2)40(61)68-19(5)44(64)18(4)67-28(11-27(44)65-9)70-34-32(53)36(43(63)12-25(52)30(45)29(35(43)54)39(59)60)69-26(13-66-22(8)51)33(34)71-41(62)31(17(3)73-14-23(37(55)56)46-20(6)49)48-42(72)74-15-24(38(57)58)47-21(7)50;1-15(2)39(60)67-18(5)43(63)17(4)66-27(10-26(43)64-9)69-33-31(52)35(42(62)11-24(51)29(44)28(34(42)53)38(58)59)68-25(12-65-21(8)50)32(33)70-40(61)30(16(3)72-13-22(36(54)55)45-19(6)48)47-41(71)73-14-23(37(56)57)46-20(7)49/h16-19,23-24,26-28,31-34,36,45,53-54,63-64H,10-15H2,1-9H3,(H,46,49)(H,47,50)(H,48,72)(H,55,56)(H,57,58)(H,59,60);15-18,22-23,25-27,30-33,35,44,52-53,62-63H,10-14H2,1-9H3,(H,45,48)(H,46,49)(H,47,71)(H,54,55)(H,56,57)(H,58,59)/t16-,17?,18?,19-,23-,24-,26?,27?,28?,31?,32?,33?,34?,36?,43+,44?;16?,17?,18-,22-,23-,25?,26?,27?,30?,31?,32?,33?,35?,42+,43?/m00/s1
InChI Key:	VSHJMNNDPYEUOT-ILYCIZJESA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/135889914

External links:
Guide to Pharmacology:	paldimycin
Main Source:	https://academic.oup.com/jac/article/19/3/405/754926?login=true
Citations:	http://jac.oxfordjournals.org/content/24/5/821 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC174800/