Compound ID | 2022

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Gramicidin

Class: Polypeptide

Spectrum of activity: Gram-positive
Details of activity: Disrupts the cell membrane and membranes of cellular organelles. Active against Gram-positive bacteria
Description: Natural product produced by Brevibacillus brevis (gramicidin A, B, C), part of a mixture with tyrocidines, known as tyrothricin. Used for minor topical infections.
Year first mentioned: 1939
Development status: Approved, off-patent
Chemical structure(s):
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Molecular weight: 1882.3
Iso. SMILES: C[C@@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC5=CNC6=CC=CC=C65)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC7=CNC8=CC=CC=C87)C(=O)NCCO)NC(=O)CNC(=O)[C@H](C(C)C)NC=O
InChI Key: ZWCXYZRRTRDGQE-SORVKSEFSA-N
Can. SMILES: CC(C)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC3=CNC4=C3C=CC=C4)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC5=CNC6=C5C=CC=C6)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC7=CNC8=C7C=CC=C8)C(=O)NCCO)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](C(C)C)NC=O
InChI: InChI=1S/C99H140N20O17/c1-51(2)37-73(109-86(123)59(17)107-81(122)49-105-96(133)82(55(9)10)106-50-121)89(126)108-60(18)87(124)117-84(57(13)14)98(135)119-85(58(15)16)99(136)118-83(56(11)12)97(134)116-80(44-64-48-104-72-34-26-22-30-68(64)72)95(132)112-76(40-54(7)8)92(129)115-79(43-63-47-103-71-33-25-21-29-67(63)71)94(131)111-75(39-53(5)6)91(128)114-78(42-62-46-102-70-32-24-20-28-66(62)70)93(130)110-74(38-52(3)4)90(127)113-77(88(125)100-35-36-120)41-61-45-101-69-31-23-19-27-65(61)69/h19-34,45-48,50-60,73-80,82-85,101-104,120H,35-44,49H2,1-18H3,(H,100,125)(H,105,133)(H,106,121)(H,107,122)(H,108,126)(H,109,123)(H,110,130)(H,111,131)(H,112,132)(H,113,127)(H,114,128)(H,115,129)(H,116,134)(H,117,124)(H,118,136)(H,119,135)/t59-,60-,73+,74+,75+,76+,77-,78-,79-,80-,82-,83-,84+,85-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/16130140
Citation: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2118194/

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