Compound ID | 302

Update compound information

Saccharomicin A

Class: Antimicrobial peptide (heptadecaglycoside)

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Effective against MRSA, even strains resistant to some classical antibiotics; membrane-active
Institute where first reported: Wyeth (Pfizer, USA)
Year first mentioned: 1999
Highest developmental phase: Preclinical
Development status: Inactive
Reason Dropped: LD(50%) of Saccharomicin A was between 2 to 360 mg/kg depending on administration method when tested on mice (1) whilst the Ed(50%) against gram-positive infections was between 0.06 to 2.6 mg/kg, when administered subcutaneously
Chemical structure(s):
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Molecular weight: 2796.1
Iso. SMILES: CC1C(C(C(C(O1)OC2C(OC(CC2(C)N)OC3C(OC(C(C3O)O)OC4C(C(OC(C4OC5CC(C(C(O5)C)O)(C)N)C)OC6C(OC(CC6(C)N)OC7C(OC(C(C7O)O)OC8C(C(OC(C8O)OC9C(OC(CC9(C)N)OC%10C(OC(C(C%10O)O)OC%11C(OC(CC%11(C)N)OC%12C(OC(C(C%12O)OS(=O)(=O)O)OC%13=C(C=C(C=C%13)/C=C/C(=O)NCCS(=O)(=O)O)O)C)C)C)C)C)O)C)C)O)C)C)O)OC%14CC(C(C(O%14)C)OC%15CC(C(C(O%15)C)OC%16CC(C(C(O%16)C)OC%17CC(C(C(O%17)C)OC%18CC(C(C(O%18)C)O)(C)N)(C)N)O)(C)N)O)O
InChI Key: YMOIRJJLVQUIJN-ORIPQNMZSA-N
Can. SMILES: CC1C(C(C(C(O1)OC2C(C)OC(CC2(C)N)OC3C(C)OC(C(C3O)O)OC4C(C(OC(C)C4OC5CC(C)(C(C(C)O5)O)N)OC6C(C)OC(CC6(C)N)OC7C(C)OC(C(C7O)O)OC8C(C(C)OC(C8O)OC9C(C)OC(CC9(C)N)OC%10C(C)OC(C(C%10O)O)OC%11C(C)OC(CC%11(C)N)OC%12C(C)OC(C(C%12O)OS(=O)(=O)O)OC%13=CC=C(/C=C/C(=O)NCCS(=O)(=O)O)C=C%13O)O)O)O)OC%14CC(C(C(C)O%14)OC%15CC(C)(C(C(C)O%15)OC%16CC(C(C(C)O%16)OC%17CC(C)(C(C(C)O%17)OC%18CC(C)(C(C(C)O%18)O)N)N)O)N)O)O
InChI: InChI=1S/C121H207N9O59S2/c1-43-76(135)95(173-66-33-62(132)88(45(3)155-66)174-69-37-116(20,124)101(54(12)159-69)181-67-34-63(133)89(46(4)156-67)175-70-38-117(21,125)102(55(13)160-70)182-75-36-115(19,123)100(148)53(11)158-75)85(144)110(165-43)186-104-57(15)161-71(39-119(104,23)127)177-91-48(6)168-108(82(141)79(91)138)184-97-87(146)112(170-51(9)94(97)180-68-35-114(18,122)99(147)52(10)157-68)188-106-59(17)163-72(41-121(106,25)129)176-90-47(5)167-107(81(140)78(90)137)183-96-77(136)44(2)166-111(86(96)145)187-105-58(16)162-73(40-120(105,24)128)178-92-49(7)169-109(83(142)80(92)139)185-103-56(14)164-74(42-118(103,22)126)179-93-50(8)171-113(98(84(93)143)189-191(152,153)154)172-64-28-26-60(32-61(64)131)27-29-65(134)130-30-31-190(149,150)151/h26-29,32,43-59,62-63,66-113,131-133,135-148H,30-31,33-42,122-129H2,1-25H3,(H,130,134)(H,149,150,151)(H,152,153,154)/b29-27+
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/139587893
Citations:
  • https://www.ncbi.nlm.nih.gov/pubmed/10898690
  • http://www.ncbi.nlm.nih.gov/pmc/articles/PMC90028/

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