CHEBI:183049 - ManNAz-DBCO-Pam3CSK4

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ChEBI Name ManNAz-DBCO-Pam3CSK4
ChEBI ID CHEBI:183049
ChEBI ASCII Name ManNAz-DBCO-Pam3CSK4
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C109H188N16O22S
Net Charge 0
Average Mass 2106.850
Monoisotopic Mass 2105.38048
InChI InChI=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
InChIKey HACHPVCYFLSKSB-UMJDSZQGSA-N
SMILES [H][C@]1(O[C@@](O)(C[C@H](O)[C@H]1NC(=O)N1N=NC2C1C1=CC=CC=C1N(CC1=C2C=CC=C1)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)C(O)=O)[C@H](O)[C@H](O)CO
Roles Classification
Biological Role(s): neoantigen
A mainly tumour-specific antigen generated by mutations in tumour cells. Neoantigens are only expressed in tumour cells.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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
MDP ChEBI
Citation Waiting for Citations Type Source
34158858 PubMed citation Europe PMC
Last Modified
22 October 2021