Compound ID | 303

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Saccharomicin B

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: 2780.1
Iso. SMILES: CC1C(C(C(C(O1)OC2C(OC(CC2(C)N)OC3C(OC(CC3O)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: VNCROLINKPTVCO-ORIPQNMZSA-N
Can. SMILES: CC1C(C(C(C(O1)OC2C(C)OC(CC2(C)N)OC3C(C)OC(CC3O)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/C121H207N9O58S2/c1-44-79(136)96(172-68-33-63(132)89(46(3)154-68)174-72-38-116(20,124)102(55(12)159-72)181-70-35-65(134)91(48(5)156-70)175-73-39-117(21,125)103(56(13)160-73)182-78-37-115(19,123)101(147)54(11)158-78)86(143)110(165-44)185-105-58(15)161-74(40-118(105,22)126)176-90-47(4)155-69(34-64(90)133)173-98-88(145)112(169-52(9)95(98)180-71-36-114(18,122)100(146)53(10)157-71)187-107-60(17)163-75(42-121(107,25)129)177-92-49(6)167-108(83(140)81(92)138)183-97-80(137)45(2)166-111(87(97)144)186-106-59(16)162-76(41-120(106,24)128)178-93-50(7)168-109(84(141)82(93)139)184-104-57(14)164-77(43-119(104,23)127)179-94-51(8)170-113(99(85(94)142)188-190(151,152)153)171-66-28-26-61(32-62(66)131)27-29-67(135)130-30-31-189(148,149)150/h26-29,32,44-60,63-65,68-113,131-134,136-147H,30-31,33-43,122-129H2,1-25H3,(H,130,135)(H,148,149,150)(H,151,152,153)/b29-27+
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/139587744
Citations:
  • https://www.ncbi.nlm.nih.gov/pubmed/10898690
  • http://www.ncbi.nlm.nih.gov/pmc/articles/PMC90028/

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