2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(1H-pyrrol-1-yl)benzoic acid

ID: ALA2289311

PubChem CID: 76309358

Max Phase: Preclinical

Molecular Formula: C17H15N3O5

Molecular Weight: 341.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)nc(Oc2cccc(-n3cccc3)c2C(=O)O)n1

Standard InChI:  InChI=1S/C17H15N3O5/c1-23-13-10-14(24-2)19-17(18-13)25-12-7-5-6-11(15(12)16(21)22)20-8-3-4-9-20/h3-10H,1-2H3,(H,21,22)

Standard InChI Key:  HWMRSTZHOPPCIH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   18.4514   -3.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4503   -4.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1583   -4.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8680   -4.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8652   -3.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1565   -2.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5763   -4.5531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5776   -5.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8692   -5.7784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8702   -6.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5791   -7.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2885   -6.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2840   -5.7739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1629   -7.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4548   -6.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9982   -6.9940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0024   -7.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5729   -2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2821   -3.3173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5698   -2.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1582   -2.1001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8189   -1.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5639   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7456   -0.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4976   -1.6247    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
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 10 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  1  0
 18 19  1  0
 18 20  2  0
  5 18  1  0
 22 23  2  0
 21 22  1  0
 23 24  1  0
 24 25  2  0
 25 21  1  0
  6 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289311

   2-(4,6-Dimethoxypyrimidin-2-yl)oxy-6-pyrrol-1-ylbenzoic acid

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: 341.32

Molecular Weight (Monoisotopic): 341.1012

AlogP: 2.78

#Rotatable Bonds: 6

Polar Surface Area: 95.70

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.06

CX Basic pKa: 0.03

CX LogP: 3.72

CX LogD: 0.26

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -0.88

References

1. NEZU Y, WADA N, SAITOH Y, TAKAHASHI S, MIYAZAWA T.  (1996)  Synthesis and Herbicidal Activity of Pyrimidinyl Salicylic and Thiosalicylic Acids,  21  (3): [10.1584/jpestics.21.293]

Source

Source(1):

• Scientific Literature