4-{2-[2-(3-Acetylamino-2,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid

ID: ALA369794

Chembl Id: CHEMBL369794

Cas Number: 87420-48-2

PubChem CID: 451714

Max Phase: Preclinical

Molecular Formula: C19H32N4O11

Molecular Weight: 492.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: muramyldipeptide | Muramyl Dipeptide|muramyldipeptide|87420-48-2|CHEBI:59414|MurNAc-L-Ala-gamma-D-Glu|Acetylmuramyl-L-alanyl-D-isoglutamine|(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|(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|MDP|53678-77-6|D-alpha-GShow More⌵

Canonical SMILES:  CC(=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

Standard 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

Standard InChI Key:  BSOQXXWZTUDTEL-ZUYCGGNHSA-N

Alternative Forms

1. Parent:

   

   ALA369794

   MURAMYLDIPEPTIDE

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 492.48

Molecular Weight (Monoisotopic): 492.2068

AlogP: -4.33

#Rotatable Bonds: 12

Polar Surface Area: 246.84

Molecular Species: ACID

HBA: 10

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 15

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.05

CX Basic pKa:

CX LogP: -4.76

CX LogD: -7.89

Aromatic Rings: 0

Heavy Atoms: 34

QED Weighted: 0.13

Np Likeness Score: 1.03

References

1. Durette PL, Dorn CP, Friedman A, Schlabach A..  (1982)  Synthesis and immunoadjuvant activities of 2-acetamido-5-O-acetyl-6-O-acyl-2-deoxy-3-O-[(R)-2-propionyl-L-alanyl-D- isoglutamine]-D-glucofuranoses as potential prodrug forms of 6-O-Acyl Derivatives of N-acetylmuramyl dipeptide.,  25  (9): [PMID:7131480] [10.1021/jm00351a005]

2. Ponpipom MM, Bugianesi RL, Shen TY, Friedman A..  (1980)  Glycolipids as potential immunologic adjuvants.,  23  (11): [PMID:7452668] [10.1021/jm00185a007]

3. Hiebert CK, Kopp WC, Richerson HB, Barfknecht CF..  (1983)  Synthesis of a biologically active fluorescent muramyl dipeptide congener.,  26  (12): [PMID:6644742] [10.1021/jm00366a014]

4. Hiebert CK, Kopp WC, Richerson HB, Barfknecht CF..  (1988)  Synthesis of fluorescent muramyl dipeptide congeners. 2.,  31  (10): [PMID:3172138] [10.1021/jm00118a029]

5. Lederer E..  (1980)  Synthetic immunostimulants derived from the bacterial cell wall.,  23  (8): [PMID:6995612] [10.1021/jm00182a001]

6. Lefrancier P, Derrien M, Jamet X, Choay J, Lederer E, Audibert F, Parant M, Parant F, Chedid L..  (1982)  Apyrogenic, adjuvant-active N-acetylmuramyl-dipeptides.,  25  (1): [PMID:7086827] [10.1021/jm00343a018]

7. Jakopin Ž, Corsini E, Gobec M, Mlinarič-Raščan I, Dolenc MS..  (2011)  Design, synthesis and biological evaluation of novel desmuramyldipeptide analogs.,  46  (9): [PMID:21669478] [10.1016/j.ejmech.2011.05.042]

8. Gobec M, Mlinarič-Raščan I, Dolenc MS, Jakopin Ž..  (2016)  Structural requirements of acylated Gly-l-Ala-d-Glu analogs for activation of the innate immune receptor NOD2.,  116  [PMID:27039337] [10.1016/j.ejmech.2016.03.030]

9. Gobec M, Tomašič T, Štimac A, Frkanec R, Trontelj J, Anderluh M, Mlinarič-Raščan I, Jakopin Ž..  (2018)  Discovery of Nanomolar Desmuramylpeptide Agonists of the Innate Immune Receptor Nucleotide-Binding Oligomerization Domain-Containing Protein 2 (NOD2) Possessing Immunostimulatory Properties.,  61  (7): [PMID:29543461] [10.1021/acs.jmedchem.7b01052]

10. Guzelj S, Nabergoj S, Gobec M, Pajk S, Klančič V, Slütter B, Frkanec R, Štimac A, Šket P, Plavec J, Mlinarič-Raščan I, Jakopin Ž..  (2021)  Structural Fine-Tuning of Desmuramylpeptide NOD2 Agonists Defines Their In Vivo Adjuvant Activity.,  64  (11.0): [PMID:34043358] [10.1021/acs.jmedchem.1c00644]

Source

Source(1):

• Scientific Literature