4-(3-(4-hydroxy-3-methoxyphenyl)-3-oxoprop-1-enyl)benzoic acid

ID: ALA4646138

PubChem CID: 9448557

Max Phase: Preclinical

Molecular Formula: C17H14O5

Molecular Weight: 298.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)/C=C/c2ccc(C(=O)O)cc2)ccc1O

Standard InChI:  InChI=1S/C17H14O5/c1-22-16-10-13(7-9-15(16)19)14(18)8-4-11-2-5-12(6-3-11)17(20)21/h2-10,19H,1H3,(H,20,21)/b8-4+

Standard InChI Key:  GADBODJYJJFTRG-XBXARRHUSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    6.8126  -26.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8115  -26.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5195  -27.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292  -26.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2264  -26.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5177  -25.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1048  -25.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3972  -26.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6894  -25.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6892  -24.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9375  -27.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9388  -28.1237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6446  -26.8968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9826  -26.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745  -25.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5674  -26.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5671  -26.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2799  -27.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9841  -26.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8598  -25.6697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600  -24.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8601  -27.3063    0.0000 O   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 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  9 14  1  0
 16 20  1  0
 20 21  1  0
 17 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4646138

   4-[(E)-3-(4-hydroxy-3-methoxyphenyl)-3-oxoprop-1-enyl]benzoic acid

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: 298.29

Molecular Weight (Monoisotopic): 298.0841

AlogP: 3.00

#Rotatable Bonds: 5

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.11

CX Basic pKa: ┄

CX LogP: 3.09

CX LogD: -0.05

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.65

Np Likeness Score: 0.38

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