N-(3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)acetamide

ID: ALA204232

Cas Number: 852315-00-5

PubChem CID: 11386747

Max Phase: Preclinical

Molecular Formula: C25H18Cl3N3O3

Molecular Weight: 514.80

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Naphthyridinone | NAPHTHYRIDINONE|CB1 inverse agonist 1|CHEMBL204232|N-(3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)acetamide|N-[3-Acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide|SCHEMBL762298|MRL-650|VHSIAYLBCLUAFT-UHFFFAOYSA-N|BDBM50176435|AKOS040732727|852315-00-5|HY-135280|CS-0110581

Canonical SMILES:  CC(=O)Nc1c(C(C)=O)c(=O)n(C)c2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12

Standard InChI:  InChI=1S/C25H18Cl3N3O3/c1-12(32)21-23(29-13(2)33)19-11-18(14-4-6-15(26)7-5-14)22(30-24(19)31(3)25(21)34)17-9-8-16(27)10-20(17)28/h4-11H,1-3H3,(H,29,33)

Standard InChI Key:  VHSIAYLBCLUAFT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -1.2473   -0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2484   -1.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336   -1.9235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5354   -0.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -0.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1788   -1.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957   -1.9280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6183   -1.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981   -0.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933   -2.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316   -1.9293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3350   -0.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0485   -0.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3370    0.5540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981    0.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836    0.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837    1.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5308    0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597   -0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9586    0.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6723    0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3877    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3848   -0.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6705   -0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9613   -1.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6757   -1.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3900   -1.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911   -2.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6720   -3.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9606   -2.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2453   -3.1556    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.1054   -3.1581    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.1028    0.9659    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
 16 17  1  0
  5 10  1  0
 17 18  2  0
  6  7  1  0
 17 19  1  0
  7  8  1  0
  8  9  1  0
 20 21  2  0
  9 10  2  0
 21 22  1  0
  5  6  1  0
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  7 11  1  0
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  1 20  1  0
  8 12  2  0
  2  3  1  0
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  9 13  1  0
 27 28  1  0
  3  6  2  0
 28 29  2  0
 13 14  1  0
 29 30  1  0
  1  2  2  0
 30 31  2  0
 31 26  1  0
  2 26  1  0
 13 15  2  0
 31 32  1  0
  5  4  2  0
 29 33  1  0
 10 16  1  0
 23 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA204232

   NAPHTHYRIDINONE

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: Yes

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: 514.80

Molecular Weight (Monoisotopic): 513.0414

AlogP: 6.39

#Rotatable Bonds: 4

Polar Surface Area: 81.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.16

CX Basic pKa: 0.46

CX LogP: 4.68

CX LogD: 4.68

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.32

Np Likeness Score: -0.96

References

1. Debenham JS, Madsen-Duggan CB, Walsh TF, Wang J, Tong X, Doss GA, Lao J, Fong TM, Schaeffer MT, Xiao JC, Huang CR, Shen CP, Feng Y, Marsh DJ, Stribling DS, Shearman LP, Strack AM, MacIntyre DE, Van der Ploeg LH, Goulet MT..  (2006)  Synthesis of functionalized 1,8-naphthyridinones and their evaluation as novel, orally active CB1 receptor inverse agonists.,  16  (3): [PMID:16263284] [10.1016/j.bmcl.2005.10.028]

2. Debenham JS, Madsen-Duggan CB, Wang J, Tong X, Lao J, Fong TM, Schaeffer MT, Xiao JC, Huang CC, Shen CP, Sloan Stribling D, Shearman LP, Strack AM, Euan Macintyre D, Hale JJ, Walsh TF..  (2009)  Pyridopyrimidine based cannabinoid-1 receptor inverse agonists: Synthesis and biological evaluation.,  19  (9): [PMID:19328684] [10.1016/j.bmcl.2009.03.005]

3. Debenham JS, Madsen-Duggan CB, Toupence RB, Walsh TF, Wang J, Tong X, Kumar S, Lao J, Fong TM, Xiao JC, Huang CR, Shen CP, Feng Y, Marsh DJ, Stribling DS, Shearman LP, Strack AM, Goulet MT..  (2010)  Furo[2,3-b]pyridine-based cannabinoid-1 receptor inverse agonists: synthesis and biological evaluation. Part 1.,  20  (4): [PMID:20096577] [10.1016/j.bmcl.2009.12.065]

4. Madsen-Duggan CB, Debenham JS, Walsh TF, Yan L, Huo P, Wang J, Tong X, Lao J, Fong TM, Xiao JC, Huang CR, Shen CP, Stribling DS, Shearman LP, Strack AM, Goulet MT, Hale JJ..  (2010)  Dihydro-pyrano[2,3-b]pyridines and tetrahydro-1,8-naphthyridines as CB1 receptor inverse agonists: synthesis, SAR and biological evaluation.,  20  (12): [PMID:20483606] [10.1016/j.bmcl.2010.04.071]

5. SGC Frankfurt.  (2021)  Data for DCP probe MRL-650,  [10.6019/CHEMBL4507287]

6.  (2021)  EUbOPEN Chemogenomics Library wave 1,  [10.6019/CHEMBL4689842]

7. EUbOPEN.  (2022)  EUbOPEN Chemogenomics Library wave 2 - DSF,  [10.6019/CHEMBL5060014]

8. EUbOPEN.  (2023)  Affinity On-target Cellular Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5210121]

9. EUbOPEN.  (2023)  Affinity Biochemical Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5210307]

10. EUbOPEN.  (2023)  Selectivity Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5212743]

Source

Source(4):

• Scientific Literature
• Donated Chemical Probes - SGC Frankfurt
• EUbOPEN Chemogenomic Library
• Literature data from EUbOPEN Chemogenomic Library