muramyl dipeptide   Click here for help

GtoPdb Ligand ID: 5024

Abbreviated name: MDP
PDB Ligand
Comment: Muramyl dipeptide (MDP) is the minimal bioactive peptidoglycan motif common to all bacteria. It is a ligand for the NOD2 pattern recognition receptor [1,3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 15
Hydrogen bond donors 8
Rotatable bonds 15
Topological polar surface area 246.84
Molecular weight 492.21
XLogP -3.78
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(O)C(C(C1O)OC(C(=O)NC(C(=O)NC(C(=O)N)CCC(=O)O)C)C)NC(=O)C
Isomeric SMILES OC[C@H]1O[C@@H](O)[C@@H]([C@H]([C@@H]1O)O[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N)CCC(=O)O)C)C)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
InChI Key BSOQXXWZTUDTEL-ZUYCGGNHSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
(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
Database Links Click here for help
CAS Registry No. 53678-77-6
ChEBI CHEBI:59414
ChEMBL Ligand CHEMBL369794
GtoPdb PubChem SID 178101721
PubChem CID 451714
RCSB PDB Ligand 3LT
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Wikipedia Muramyl_dipeptide

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Tocris
Muramyl Dipeptide
Cat. No. 6366