Compound ID | 2123

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Gargantulide A, B, C

Class: Macrolide

Spectrum of activity: Gram-positive
Details of activity: Inhibits Sec-dependent protein translocation across the inner membrane. Active against Gram-positive bacteria.
Description: Natural product produced by Amycolatopsis (formerly Streptomyces)
Year first mentioned: 2015
Development status: Experimental
Chemical structure(s):
Gargantulide C
Click here for structure editor
Molecular weight: 2230.82
Iso. SMILES: CCC[C@H](CC[C@@H]([C@H](C)[C@H](C[C@@H](C[C@@H](CCC[C@@H](CC[C@H](C)CCCCN)O)O[C@@H]1[C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O)NC)O)[C@@H]3[C@H]([C@H](C[C@H](C[C@H]([C@@H]([C@@H]([C@H]([C@@H](C[C@H](C[C@@H](C[C@H](C[C@@H](CCC[C@H](C[C@@H]([C@H]([C@H]([C@@H](C=C([C@H](CC(=O)[C@@H]([C@@H](CCCC[C@@H]([C@@H]([C@H](CC[C@@H]([C@H](CCCCC(=O)O3)C)O)C)O)C)O)C)O)C)OC4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C)O)O)O)O)O)O)O)C)O)C)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C
InChI Key: PORSANQCUOUJQE-FUQBXQPNSA-N
Can. SMILES: CCC[C@H](CC[C@@H]([C@H](C)[C@H](C[C@@H](C[C@@H](CCC[C@@H](CC[C@H](C)CCCCN)O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](C)O2)O)NC)O)[C@@H]3[C@@H](C)[C@H](C[C@H](C[C@H]([C@H](C)[C@@H]([C@@H](C)[C@@H](C[C@H](C[C@@H](C[C@H](C[C@@H](CCC[C@H](C[C@@H]([C@@H](C)[C@H]([C@@H](C=C(C)[C@H](CC(=O)[C@H](C)[C@@H](CCCC[C@H](C)[C@@H]([C@@H](C)CC[C@@H]([C@@H](C)CCCCC(=O)O3)O)O)O)O)OC4[C@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O
InChI: InChI=1S/C110H208N2O42/c1-15-24-67(36-39-85(148-107-100(140)92(112-14)96(136)66(13)146-107)61(8)80(127)48-74(122)45-76(147-108-103(143)99(139)90(54-115)151-108)31-23-28-68(116)37-34-55(2)25-20-21-40-111)106-65(12)86(149-109-104(144)101(141)97(137)88(52-113)152-109)50-75(123)49-83(130)63(10)94(134)62(9)82(129)47-73(121)44-72(120)43-71(119)42-69(117)29-22-30-70(118)46-81(128)64(11)95(135)87(150-110-105(145)102(142)98(138)89(53-114)153-110)41-59(6)79(126)51-84(131)60(7)78(125)32-18-16-27-57(4)93(133)58(5)35-38-77(124)56(3)26-17-19-33-91(132)154-106/h41,55-58,60-83,85-90,92-110,112-130,133-145H,15-40,42-54,111H2,1-14H3/t55-,56+,57+,58+,60-,61-,62+,63+,64-,65+,66-,67-,68+,69-,70-,71+,72-,73+,74-,75+,76-,77+,78-,79+,80+,81+,82-,83-,85+,86+,87-,88-,89-,90-,92+,93+,94-,95-,96-,97-,98-,99-,100-,101+,102+,103+,104-,105+,106+,107+,108+,109-,110?/m1/s1
Gargantulide B
Click here for structure editor
Molecular weight: 2392.96
Iso. SMILES: CCC[C@H](CC[C@@H]([C@H](C)[C@H](C[C@@H](C[C@@H](CCC[C@@H](CC[C@H](C)CCCCN)O)O[C@@H]1[C@H]([C@@H]([C@H](O1)CO)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C)O)NC)O)[C@@H]4[C@H]([C@H](C[C@H](C[C@H]([C@@H]([C@@H]([C@H]([C@@H](C[C@H](C[C@@H](C[C@H](C[C@@H](CCC[C@H](C[C@@H]([C@H]([C@H]([C@@H](C=C([C@H](CC(=O)[C@@H]([C@@H](CCCC[C@@H]([C@@H]([C@H](CC[C@@H]([C@H](CCCCC(=O)O4)C)O)C)O)C)O)C)O)C)OC5[C@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)C)O)O)O)O)O)O)O)C)O)C)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C
InChI Key: QKRNMRPMUJJGNI-ZAHQSYIJSA-N
Can. SMILES: CCC[C@H](CC[C@@H]([C@H](C)[C@H](C[C@@H](C[C@@H](CCC[C@@H](CC[C@H](C)CCCCN)O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C)O3)O)NC)O)[C@@H]4[C@@H](C)[C@H](C[C@H](C[C@H]([C@H](C)[C@@H]([C@@H](C)[C@@H](C[C@H](C[C@@H](C[C@H](C[C@@H](CCC[C@H](C[C@@H]([C@@H](C)[C@H]([C@@H](C=C(C)[C@H](CC(=O)[C@H](C)[C@@H](CCCC[C@H](C)[C@@H]([C@@H](C)CC[C@@H]([C@@H](C)CCCCC(=O)O4)O)O)O)O)OC5[C@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@@H](CO)O6)O)O)O
InChI: InChI=1S/C116H218N2O47/c1-15-24-68(36-39-86(158-112-103(147)94(118-14)98(142)67(13)155-112)62(8)84(136)50-77(157-114-108(152)104(148)99(143)89(52-119)161-114)49-76(156-113-107(151)102(146)92(55-122)162-113)31-23-28-69(123)37-34-56(2)25-20-21-40-117)111-66(12)87(159-115-109(153)105(149)100(144)90(53-120)163-115)48-75(129)47-83(135)64(10)96(140)63(9)82(134)46-74(128)44-73(127)43-72(126)42-70(124)29-22-30-71(125)45-81(133)65(11)97(141)88(160-116-110(154)106(150)101(145)91(54-121)164-116)41-60(6)80(132)51-85(137)61(7)79(131)32-18-16-27-58(4)95(139)59(5)35-38-78(130)57(3)26-17-19-33-93(138)165-111/h41,56-59,61-84,86-92,94-116,118-136,139-154H,15-40,42-55,117H2,1-14H3/t56-,57+,58+,59+,61-,62-,63+,64+,65-,66+,67-,68-,69+,70-,71-,72+,73-,74+,75+,76-,77-,78+,79-,80+,81+,82-,83-,84+,86+,87+,88-,89-,90-,91-,92-,94+,95+,96-,97-,98-,99-,100-,101-,102-,103-,104+,105+,106+,107+,108-,109-,110+,111+,112+,113+,114-,115-,116?/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/170988219
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/170988220
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5125438/
  • https://pubs.rsc.org/en/content/articlelanding/2022/qo/d1qo01480c

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