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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:59414
CAS Number: 87420-48-2
TTD ID: D05UGC
VARIDT ID: DR01361

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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Beta-2-microglobulin (B2M)	OTDWN6NX	B2MG_HUMAN	Gene/Protein Processing	[4]
CD83 antigen (CD83)	OT1V4WQF	CD83_HUMAN	Gene/Protein Processing	[5]
Interleukin-12 subunit beta (IL12B)	OT0JF8A3	IL12B_HUMAN	Protein Interaction/Cellular Processes	[4]
Interleukin-6 (IL6)	OTUOSCCU	IL6_HUMAN	Protein Interaction/Cellular Processes	[4]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[5]
NF-kappa-B inhibitor alpha (NFKBIA)	OTFT924M	IKBA_HUMAN	Post-Translational Modifications	[6]
T-lymphocyte activation antigen CD80 (CD80)	OTJBLUQE	CD80_HUMAN	Gene/Protein Processing	[5]
T-lymphocyte activation antigen CD86 (CD86)	OTJCSBPC	CD86_HUMAN	Gene/Protein Processing	[5]
Toll-like receptor 2 (TLR2)	OTGO5P4R	TLR2_HUMAN	Gene/Protein Processing	[4]
Toll-like receptor 4 (TLR4)	OTP7ML3S	TLR4_HUMAN	Gene/Protein Processing	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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	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.
5	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.
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.