1-(5-((cis)-3-(Hydroxymethyl)cyclobutyl)-4-((5-methylpyridin-3-yl)oxy)pyridin-2-yl)-3-methylurea

ID: ALA4529989

PubChem CID: 155545937

Max Phase: Preclinical

Molecular Formula: C18H22N4O3

Molecular Weight: 342.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)Nc1cc(Oc2cncc(C)c2)c([C@H]2C[C@@H](CO)C2)cn1

Standard InChI:  InChI=1S/C18H22N4O3/c1-11-3-14(8-20-7-11)25-16-6-17(22-18(24)19-2)21-9-15(16)13-4-12(5-13)10-23/h3,6-9,12-13,23H,4-5,10H2,1-2H3,(H2,19,21,22,24)/t12-,13+

Standard InChI Key:  ZFKQRXNFXUUWGJ-BETUJISGSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   26.9033  -18.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9022  -19.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6170  -19.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3335  -19.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3306  -18.4968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6152  -18.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1874  -19.7397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1867  -20.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4718  -20.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4708  -21.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1855  -22.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9026  -21.7969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9001  -20.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7558  -22.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0486  -19.7387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7625  -19.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4776  -19.7364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7612  -18.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4750  -18.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1888  -18.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9758  -17.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1790  -17.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3927  -18.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4644  -17.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7500  -17.5052    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
  2  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
  4 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 20  1  1  1
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 20  1  0
 22 24  1  1
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4529989

   ---

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: 342.40

Molecular Weight (Monoisotopic): 342.1692

AlogP: 2.81

#Rotatable Bonds: 5

Polar Surface Area: 96.37

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.82

CX Basic pKa: 5.39

CX LogP: 1.43

CX LogD: 1.42

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -0.53

References

1. Kohn TJ, Du X, Lai S, Xiong Y, Komorowski R, Veniant M, Fu Z, Jiao X, Pattaropong V, Chow D, Cardozo M, Jin L, Conn M, DeWolf WE, Kraser CF, Hinklin RJ, Boys ML, Medina JC, Houze J, Dransfield P, Coward P..  (2016)  5-Alkyl-2-urea-Substituted Pyridines: Identification of Efficacious Glucokinase Activators with Improved Properties.,  7  (7): [PMID:27437074] [10.1021/acsmedchemlett.6b00145]

Source

Source(1):

• Scientific Literature