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CHEBI:183049 - ManNAz-DBCO-Pam3CSK4

ChEBI IDCHEBI:183049
ChEBI NameManNAz-DBCO-Pam3CSK4
Stars
ASCII NameManNAz-DBCO-Pam3CSK4
DefinitionA carbohydrate derivative formed from a tetra-acetyl-N-azidoacetylmannosamine (AC4ManNAz) linked through a dibenzylcyclooctyl group (DBCO) to the triacylipopeptide N-palmitoyl-S-[2,3-bis(palmitoyloxy)propyl]-Cys-Ser-Lys-Lys-Lys-Lys (Pam3CSK4; CHEBI:134411). Commonly abbreviated to MDP, it has been developed as an artificial neoantigen on tumour cells to enhance tumour immunogenicity, able to significantly improve the response and the clinical outcome of immune checkpoint inhibitors (ICIs).
Last Modified22 October 2021
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC109H188N16O22S
Net Charge0
Average Mass2106.860
Monoisotopic Mass2105.38048
SMILES[H][C@@]1([C@H](O)[C@H](O)CO)O[C@](O)(C(=O)O)C[C@H](O)[C@H]1NC(=O)N1N=NC2c3ccccc3CN(C(=O)CCNC(=O)[C@@H](CCCCN)NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](CO)NC(=O)[C@@H](CSCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)NC(=O)CCCCCCCCCCCCCCC)c3ccccc3C21
InChIInChI=1S/C109H188N16O22S/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-63-92(130)115-88(78-148-77-80(146-95(133)65-42-39-36-33-30-27-24-21-18-15-12-9-6-3)76-145-94(132)64-41-38-35-32-29-26-23-20-17-14-11-8-5-2)106(140)120-87(74-126)105(139)119-86(61-50-54-70-113)104(138)118-85(60-49-53-69-112)103(137)117-84(59-48-52-68-111)102(136)116-83(58-47-51-67-110)101(135)114-71-66-93(131)124-73-79-55-43-44-56-81(79)96-98(82-57-45-46-62-89(82)124)125(123-122-96)108(143)121-97-90(128)72-109(144,107(141)142)147-100(97)99(134)91(129)75-127/h43-46,55-57,62,80,83-88,90-91,96-100,126-129,134,144H,4-42,47-54,58-61,63-78,110-113H2,1-3H3,(H,114,135)(H,115,130)(H,116,136)(H,117,137)(H,118,138)(H,119,139)(H,120,140)(H,121,143)(H,141,142)/t80?,83-,84-,85-,86-,87-,88-,90+,91-,96?,97-,98?,99-,100-,109+/m1/s1
InChIKeyHACHPVCYFLSKSB-UMJDSZQGSA-N
Roles Classification
Biological Roles:
epitope  The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
neoantigen  A mainly tumour-specific antigen generated by mutations in tumour cells. Neoantigens are only expressed in tumour cells.
ChEBI Ontology
Outgoing Relation(s)
ManNAz-DBCO-Pam3CSK4 (CHEBI:183049) has role epitope (CHEBI:53000)
ManNAz-DBCO-Pam3CSK4 (CHEBI:183049) has role neoantigen (CHEBI:183050)
ManNAz-DBCO-Pam3CSK4 (CHEBI:183049) is a carbohydrate derivative (CHEBI:63299)
IUPAC Name 
5-{[8-(3-{[(2R)-6-amino-2-{[(2R)-6-amino-2-{[(2R)-6-amino-2-({S-[2,3-bis(hexadecanoyloxy)propyl]-N-hexadecanoyl-D-cysteinyl-D-seryl-D-lysyl}amino)hexanoyl]amino}hexanoyl]amino}hexanoyl]amino}propanoyl)-3a,8,9,13b-tetrahydro-3H-dibenzo[b,f][1,2,3]triazolo[4,5-d]azocine-3-carbonyl]amino}-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonic acid
Synonym  Source
MDPChEBI
Citations