CHEBI:59414 - muramyl dipeptide

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ChEBI Name muramyl dipeptide
ChEBI ID CHEBI:59414
Definition Muramyl dipeptide is a peptidoglycan constituent of both Gram positive and Gram negative bacteria. It is composed of N-acetylmuramic acid linked by its lactic acid moiety to the N-terminus of the dipeptide L-alanyl-D-isoglutamine.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Steve Jupe
Secondary ChEBI IDs CHEBI:378548
Supplier Information
Download Molfile XML SDF
Formula C19H32N4O11
Net Charge 0
Average Mass 492.47760
Monoisotopic Mass 492.207
InChI InChI=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
InChIKey BSOQXXWZTUDTEL-ZUYCGGNHSA-N
SMILES C[C@H](NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O)C(=O)N[C@H](CCC(O)=O)C(N)=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): 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(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing muramyl dipeptide (CHEBI:59414) has role immunological adjuvant (CHEBI:50847)
muramyl dipeptide (CHEBI:59414) is a glycopeptide (CHEBI:24396)
Synonyms Sources
Acetylmuramyl-alanyl-isoglutamine ChemIDplus
Acetylmuramyl-L-alanyl-D-isoglutamine SUBMITTER
MDP SUBMITTER
MurNAc-L-Ala-γ-D-Glu ChEBI
N-acetylmuramyl-L-alanyl-D-isoglutamine ChEBI
N2-(N-(N-Acetylmuramoyl)-L-alanyl)-D-α-glutamine ChemIDplus
Manual Xrefs Databases
DE2450355 Patent
US4235771 Patent
View more database links
Registry Numbers Types Sources
5323915 Beilstein Registry Number Beilstein
53678-77-6 CAS Registry Number ChemIDplus
Last Modified
20 September 2010