3-{4-[(4-chlorobenzyl)oxy]-3-methoxyphenyl}-N-(4-chloro-2,5-dimethoxyphenyl)acrylamide

ID: ALA571713

PubChem CID: 45484038

Max Phase: Preclinical

Molecular Formula: C25H25Cl2NO5

Molecular Weight: 490.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(=O)CCc2ccc(OCc3ccc(Cl)cc3)c(OC)c2)c(OC)cc1Cl

Standard InChI:  InChI=1S/C25H25Cl2NO5/c1-30-22-14-20(23(31-2)13-19(22)27)28-25(29)11-7-16-6-10-21(24(12-16)32-3)33-15-17-4-8-18(26)9-5-17/h4-6,8-10,12-14H,7,11,15H2,1-3H3,(H,28,29)

Standard InChI Key:  NDZJQDZKTAJEHO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.8116   -4.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6355   -4.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0466   -3.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6350   -3.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8080   -3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4005   -3.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5748   -3.9448    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.8723   -3.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2850   -4.6559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1107   -4.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5200   -5.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3450   -5.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7589   -4.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3417   -3.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5181   -3.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1023   -3.2291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5121   -2.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5846   -4.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9981   -5.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8238   -5.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2360   -4.6543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2375   -6.0845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0617   -4.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4704   -5.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2953   -5.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7083   -4.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2902   -3.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4666   -3.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0491   -3.2260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4572   -2.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5340   -4.6492    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.7082   -6.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5332   -6.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  3  8  1  0
 16 17  1  0
 13 18  1  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
  2  3  1  0
 20 22  2  0
 10 11  2  0
 21 23  1  0
  5  6  2  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 12 13  2  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 28 23  1  0
 13 14  1  0
 28 29  1  0
  6  7  1  0
 29 30  1  0
 14 15  2  0
 15 10  1  0
  3  4  2  0
 26 31  1  0
 25 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA571713

   N-(4-chloro-2,5-dimethoxy-phenyl)-3-[4-[(4-chlorophenyl)methoxy]-3-methoxy-phenyl]propanamide

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: 490.38

Molecular Weight (Monoisotopic): 489.1110

AlogP: 6.17

#Rotatable Bonds: 10

Polar Surface Area: 66.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.25

CX Basic pKa: ┄

CX LogP: 5.79

CX LogD: 5.79

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -0.98

References

1. Gupta RK, Thakur TS, Desiraju GR, Tyagi JS..  (2009)  Structure-based design of DevR inhibitor active against nonreplicating Mycobacterium tuberculosis.,  52  (20): [PMID:19827833] [10.1021/jm900358q]

Source

Source(1):

• Scientific Literature