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CHEBI:134411 - N-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys

ChEBI IDCHEBI:134411
ChEBI NameN-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys
Stars
ASCII NameN-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys
DefinitionA triacyl lipopeptide that is N-palmitoyl-Cys-Ser-Lys-Lys-Lys-Lys in which the side-chain thiol hydrogen on the Cys residue has been replaced by a 2,3-bis(palmitoyloxy)propyl group.
Last Modified8 May 2017
SubmitterSandra Orchard
DownloadsMolfile
FormulaC79H152N10O13S
Net Charge0
Average Mass1482.209
Monoisotopic Mass1481.12611
SMILESCCCCCCCCCCCCCCCC(=O)OCC(CSC[C@H](NC(=O)CCCCCCCCCCCCC)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)O)OC(=O)CCCCCCCCCCCCCCC
InChIInChI=1S/C79H152N10O13S/c1-4-7-10-13-16-19-22-24-27-30-33-36-39-54-72(92)101-61-64(102-73(93)55-40-37-34-31-28-25-23-20-17-14-11-8-5-2)62-103-63-70(84-71(91)53-38-35-32-29-26-21-18-15-12-9-6-3)78(98)89-69(60-90)77(97)87-66(50-42-46-57-81)75(95)85-65(49-41-45-56-80)74(94)86-67(51-43-47-58-82)76(96)88-68(79(99)100)52-44-48-59-83/h64-70,90H,4-63,80-83H2,1-3H3,(H,84,91)(H,85,95)(H,86,94)(H,87,97)(H,88,96)(H,89,98)(H,99,100)/t64?,65-,66-,67-,68-,69-,70-/m0/s1
InChIKeyACYXXCRNFRQHBB-RXUNMRDHSA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
Toll-like receptor 2 agonist  An agonist that selectively binds to and activates the Toll-like receptor 2 (TLR 2, TLR-2) protein.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
N-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys (CHEBI:134411) has role antineoplastic agent (CHEBI:35610)
N-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys (CHEBI:134411) has role neuroprotective agent (CHEBI:63726)
N-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys (CHEBI:134411) has role Toll-like receptor 2 agonist (CHEBI:77161)
N-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys (CHEBI:134411) is a lipopeptide antibiotic (CHEBI:25061)
N-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys (CHEBI:134411) is a pentapeptide (CHEBI:48545)
N-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys (CHEBI:134411) is a triacyl lipopeptide (CHEBI:60192)
IUPAC Name 
S-[2,3-bis(hexadecanoyloxy)propyl]-N-tetradecanoyl-L-cysteinyl-L-seryl-L-lysyl-L-lysyl-L-lysyl-L-lysine
Synonyms  Source
N-hexadecanoyl-S-[2,3-bis(hexadecanoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-LysChEBI
Pam3CSK4ChEBI
Tripalmitoyl-cysteinyl-seryl-lysine(4)ChemIDplus
Pam(3)-cys-ser-(lys)(4)ChemIDplus
N-Palmitoyl-S-(2,3-bis(palmitoyloxy)propyl)cysteinyl-seryl-lysyl-lysyl-lysyl-lysineChemIDplus
Registry NumbersSources
CAS:112208-00-1ChemIDplus
Citations