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

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ChEBI Name N-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys
ChEBI ID CHEBI:134411
ChEBI ASCII Name N-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys
Definition A 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lipopeptide that is N-palmitoyl-Cys-Ser-Lys-Lys-Lys-Lys in which the side-chain thiol hydrogen on the Cys residue has been replaced by a 2,3-bis(palmitoyloxy)propyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Sandra Orchard
Supplier Information
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Formula C79H152N10O13S
Net Charge 0
Average Mass 1482.181
Monoisotopic Mass 1481.12611
InChI InChI=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
InChIKey ACYXXCRNFRQHBB-RXUNMRDHSA-N
SMILES C(CCCCCCCC)CCCCC(N[C@H](C(=O)N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(=O)N[C@H](C(=O)O)CCCCN)CCCCN)=O)CCCCN)=O)CCCCN)=O)CO)CSCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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.
(via peptide antibiotic )
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
N-hexadecanoyl-S-[2,3-bis(hexadecanoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys ChEBI
N-Palmitoyl-S-(2,3-bis(palmitoyloxy)propyl)cysteinyl-seryl-lysyl-lysyl-lysyl-lysine ChemIDplus
Pam(3)-cys-ser-(lys)(4) ChemIDplus
Pam3CSK4 ChEBI
Tripalmitoyl-cysteinyl-seryl-lysine(4) ChemIDplus
Registry Number Type Source
112208-00-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
08 May 2017