6-(4-chloro-3-cyclopropoxyphenyl)pyrimidine-4-carboxylic acid

ID: ALA4740126

PubChem CID: 71282667

Max Phase: Preclinical

Molecular Formula: C14H11ClN2O3

Molecular Weight: 290.71

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(-c2ccc(Cl)c(OC3CC3)c2)ncn1

Standard InChI:  InChI=1S/C14H11ClN2O3/c15-10-4-1-8(5-13(10)20-9-2-3-9)11-6-12(14(18)19)17-7-16-11/h1,4-7,9H,2-3H2,(H,18,19)

Standard InChI Key:  SIYCDJHEVASOGW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    5.3227  -11.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216  -12.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0296  -12.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7393  -12.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7364  -11.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0278  -10.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4396  -10.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1491  -11.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8548  -10.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8522   -9.9708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1379   -9.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4352   -9.9780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5648  -11.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5675  -12.0137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2711  -10.7856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6149  -10.7970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9073  -11.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0888  -11.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4975  -11.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6135  -12.4330    0.0000 Cl  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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  5  7  1  0
 13 14  1  0
 13 15  2  0
  9 13  1  0
  1 16  1  0
 16 17  1  0
 18 17  1  0
 19 18  1  0
 17 19  1  0
  2 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740126

   6-(4-Chloro-3-cyclopropyloxyphenyl)pyrimidine-4-carboxylic 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: 290.71

Molecular Weight (Monoisotopic): 290.0458

AlogP: 3.04

#Rotatable Bonds: 4

Polar Surface Area: 72.31

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.76

CX Basic pKa: 5.24

CX LogP: 1.41

CX LogD: -0.30

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.94

Np Likeness Score: -0.62

References

1. Kimura H,Suda H,Kassai M,Endo M,Deai Y,Yahata M,Miyajima M,Isobe Y.  (2021)  N-(6-phenylpyridazin-3-yl)benzenesulfonamides as highly potent, brain-permeable, and orally active kynurenine monooxygenase inhibitors.,  33  [PMID:33359168] [10.1016/j.bmcl.2020.127753]

2. Tsuboi K, Kimura H, Nakatsuji Y, Kassai M, Deai Y, Isobe Y..  (2021)  Discovery of N-(6-(5-fluoro-2-(piperidin-1-yl)phenyl)pyridazin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)methanesulfonamide as a brain-permeable and metabolically stable kynurenine monooxygenase inhibitor.,  44  [PMID:34015507] [10.1016/j.bmcl.2021.128115]

Source

Source(1):

• Scientific Literature