2-((6-((4-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl)methyl)pyridin-2-yl)oxy)benzoic acid

ID: ALA4873321

PubChem CID: 164625323

Max Phase: Preclinical

Molecular Formula: C23H24N4O5

Molecular Weight: 436.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cn(C2CCN(Cc3cccc(Oc4ccccc4C(=O)O)n3)CC2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C23H24N4O5/c1-15-13-27(23(31)25-21(15)28)17-9-11-26(12-10-17)14-16-5-4-8-20(24-16)32-19-7-3-2-6-18(19)22(29)30/h2-8,13,17H,9-12,14H2,1H3,(H,29,30)(H,25,28,31)

Standard InChI Key:  UEEHBISYPBIBJH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   14.2540  -21.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2529  -22.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9609  -22.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6706  -22.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6678  -21.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9591  -21.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3789  -22.9027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0860  -22.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7946  -22.9030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5012  -22.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5003  -21.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7870  -21.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0834  -21.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2093  -22.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9166  -22.4924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6240  -22.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3292  -22.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3325  -21.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6245  -21.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9132  -21.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0413  -21.2754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7471  -21.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4538  -21.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4602  -20.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7538  -20.0567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0409  -20.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1588  -21.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1706  -20.0654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3346  -20.0507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9616  -23.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2537  -24.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6692  -24.1335    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
  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
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 26  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 23 27  1  0
 24 28  2  0
 26 29  2  0
 30 31  1  0
 30 32  2  0
  3 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873321

   ---

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: 436.47

Molecular Weight (Monoisotopic): 436.1747

AlogP: 2.57

#Rotatable Bonds: 6

Polar Surface Area: 117.52

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.51

CX Basic pKa: 7.32

CX LogP: -0.58

CX LogD: -0.83

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.61

Np Likeness Score: -1.02

References

1. Song L, Merceron R, Hulpia F, Lucía A, Gracia B, Jian Y, Risseeuw MDP, Verstraelen T, Cos P, Aínsa JA, Boshoff HI, Munier-Lehmann H, Savvides SN, Van Calenbergh S..  (2021)  Structure-aided optimization of non-nucleoside M. tuberculosis thymidylate kinase inhibitors.,  225  [PMID:34450493] [10.1016/j.ejmech.2021.113784]

Source

Source(1):

• Scientific Literature