4-(3-(naphthalen-1-yl)-3-oxoprop-1-enyl)benzoic acid

ID: ALA4637558

PubChem CID: 25756573

Max Phase: Preclinical

Molecular Formula: C20H14O3

Molecular Weight: 302.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(/C=C/C(=O)c2cccc3ccccc23)cc1

Standard InChI:  InChI=1S/C20H14O3/c21-19(13-10-14-8-11-16(12-9-14)20(22)23)18-7-3-5-15-4-1-2-6-17(15)18/h1-13H,(H,22,23)/b13-10+

Standard InChI Key:  JVSJPWANJHSPSI-JLHYYAGUSA-N

Molfile:  

 
     RDKit          2D

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   30.7382  -25.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7370  -26.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4451  -27.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1547  -26.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1519  -25.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4433  -25.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0304  -25.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3228  -25.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6150  -25.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6148  -24.5492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8631  -27.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8644  -27.8182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5702  -26.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9082  -25.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4927  -26.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2055  -26.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9097  -26.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4929  -25.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1993  -25.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1986  -24.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4921  -24.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7850  -24.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7893  -25.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 14 19  2  0
 18 15  2  0
 15 16  1  0
 16 17  2  0
 17 14  1  0
  9 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4637558

   (2e)-1-(2'-Naphthyl)-3-(4-carboxyphenyl)-2-propen-1-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 302.33

Molecular Weight (Monoisotopic): 302.0943

AlogP: 4.43

#Rotatable Bonds: 4

Polar Surface Area: 54.37

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.11

CX Basic pKa: ┄

CX LogP: 4.54

CX LogD: 1.44

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.57

Np Likeness Score: -0.12

References

1. de Souza ACA, Mori M, Sens L, Rocha RF, Tizziani T, de Souza LFS, Domeneghini Chiaradia-Delatorre L, Botta M, Nunes RJ, Terenzi H, Menegatti ACO..  (2020)  A chalcone derivative binds a putative allosteric site of YopH: Inhibition of a virulence factor of Yersinia.,  30  (16): [PMID:32631548] [10.1016/j.bmcl.2020.127350]

Source

Source(1):

• Scientific Literature