Details of the Drug

General Information of Drug (ID: DM4FR71)

Drug Name
muramyl dipeptide
Synonyms
Muramyl Dipeptide; N-Acetylmuramyl-L-alanyl-D-isoglutamine; muramyldipeptide; CHEBI:59414; MurNAc-L-Ala-gamma-D-Glu; Acetylmuramyl-L-alanyl-D-isoglutamine; Acetylmuramyl-alanyl-isoglutamine; 87420-48-2; 53678-77-6; (4r)-4-[[(2s)-2-[[(2r)-2-[(2r,3s,4r,5r,6r)-5-Acetamido-2-(Hydroxymethyl)-3,6-Bis(Oxidanyl)oxan-4-Yl]oxypropanoyl]amino]propanoyl]amino]-5-Azanyl-5-Oxidanylidene-Pentanoic Acid
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 492.5
Logarithm of the Partition Coefficient (xlogp) -3.7
Rotatable Bond Count (rotbonds) 12
Hydrogen Bond Donor Count (hbonddonor) 8
Hydrogen Bond Acceptor Count (hbondacc) 11
Chemical Identifiers
Formula
C19H32N4O11
IUPAC Name
(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
Canonical SMILES
C[C@@H](C(=O)N[C@H](CCC(=O)O)C(=O)N)NC(=O)[C@@H](C)O[C@@H]1[C@H]([C@@H](O[C@@H]([C@H]1O)CO)O)NC(=O)C
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
Cross-matching ID
PubChem CID
451714
ChEBI ID
CHEMBL59414
CAS Number
87420-48-2
TTD ID
D05UGC
VARIDT ID
DR01361
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
NLR pyrin domain containing 1 (NLRP1) TTQX29T NLRP1_HUMAN Agonist [2]
Pattern recognition receptor NOD2 (NOD2) TTYPUHA NOD2_HUMAN Agonist [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
CD83 antigen (CD83) OT1V4WQF CD83_HUMAN Gene/Protein Processing [4]
Interleukin-12 subunit beta (IL12B) OT0JF8A3 IL12B_HUMAN Protein Interaction/Cellular Processes [5]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [4]
T-lymphocyte activation antigen CD80 (CD80) OTJBLUQE CD80_HUMAN Gene/Protein Processing [4]
Transcription factor p65 (RELA) OTUJP9CN TF65_HUMAN Gene/Protein Processing [6]
Tumor necrosis factor receptor superfamily member 5 (CD40) OT5YU2XB TNR5_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5024).
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 1768).
3 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 1763).
4 Synergistic effect of Nod1 and Nod2 agonists with toll-like receptor agonists on human dendritic cells to generate interleukin-12 and T helper type 1 cells. Infect Immun. 2005 Dec;73(12):7967-76. doi: 10.1128/IAI.73.12.7967-7976.2005.
5 Dendritic cell maturation induced by muramyl dipeptide (MDP) derivatives: monoacylated MDP confers TLR2/TLR4 activation. J Immunol. 2005 Jun 1;174(11):7096-103. doi: 10.4049/jimmunol.174.11.7096.
6 Inhibition of Nod2 signaling and target gene expression by curcumin. Mol Pharmacol. 2008 Jul;74(1):274-81. doi: 10.1124/mol.108.046169. Epub 2008 Apr 15.