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CHEBI:59414 - muramyl dipeptide

ChEBI IDCHEBI:59414
ChEBI Namemuramyl dipeptide
Stars
DefinitionA glycopeptide that is N-propionyl-L-alanyl-D-α-glutamine in which the pro-R hydrogen of the propionyl group has been replaced by the oxygen at position 3 of 2-acetamido-2-deoxy-β-D-glucopyranose. A peptidoglycan constituent of both Gram-positive and Gram-negative bacteria.
Secondary ChEBI IDCHEBI:378548
Last Modified26 November 2019
Submittersjupe
DownloadsMolfile
FormulaC19H32N4O11
Net Charge0
Average Mass492.482
Monoisotopic Mass492.20676
SMILESCC(=O)N[C@@H]1[C@@H](O[C@H](C)C(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(N)=O)[C@H](O)[C@@H](CO)O[C@H]1O
InChIInChI=1S/C19H32N4O11/c1-7(17(30)23-10(16(20)29)4-5-12(26)27)21-18(31)8(2)33-15-13(22-9(3)25)19(32)34-11(6-24)14(15)28/h7-8,10-11,13-15,19,24,28,32H,4-6H2,1-3H3,(H2,20,29)(H,21,31)(H,22,25)(H,23,30)(H,26,27)/t7-,8+,10+,11+,13+,14+,15+,19+/m0/s1
InChIKeyBSOQXXWZTUDTEL-ZUYCGGNHSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
immunological adjuvant  A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
Application:
immunological adjuvant  A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
ChEBI Ontology
Outgoing Relation(s)
muramyl dipeptide (CHEBI:59414) has role immunological adjuvant (CHEBI:50847)
muramyl dipeptide (CHEBI:59414) is a glycopeptide (CHEBI:24396)
muramyl dipeptide (CHEBI:59414) is conjugate acid of N-acetyl-β-D-muramoyl-L-alanyl-D-isoglutamine(1−) (CHEBI:194491)
Incoming Relation(s)
N-acetyl-β-D-muramoyl-L-alanyl-D-isoglutamine(1−) (CHEBI:194491) is conjugate base of muramyl dipeptide (CHEBI:59414)
Synonyms  Source
MDPSUBMITTER
Acetylmuramyl-L-alanyl-D-isoglutamineSUBMITTER
N-acetylmuramyl-L-alanyl-D-isoglutamineChEBI
Acetylmuramyl-alanyl-isoglutamineChemIDplus
N2-(N-(N-Acetylmuramoyl)-L-alanyl)-D-α-glutamineChemIDplus
MurNAc-L-Ala-γ-D-GluChEBI
Manual XrefsDatabases
DE2450355Patent
US4235771Patent
Registry NumbersSources
Beilstein:5323915Beilstein
CAS:53678-77-6ChemIDplus