ID: ALA3794064

Max Phase: Preclinical

Molecular Formula: C23H17F3N4O4

Molecular Weight: 470.41

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)C1CN(Cc2ccc(-c3noc(-c4onc(-c5ccccc5)c4C(F)(F)F)n3)cc2)C1

Standard InChI:  InChI=1S/C23H17F3N4O4/c24-23(25,26)17-18(14-4-2-1-3-5-14)28-33-19(17)21-27-20(29-34-21)15-8-6-13(7-9-15)10-30-11-16(12-30)22(31)32/h1-9,16H,10-12H2,(H,31,32)

Standard InChI Key:  RRPYZEWVBYBTJC-UHFFFAOYSA-N

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

Properties

Molecular Weight: 470.41

Molecular Weight (Monoisotopic): 470.1202

AlogP: 4.59

#Rotatable Bonds: 6

Polar Surface Area: 105.49

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.12

CX Basic pKa: 8.39

CX LogP: 1.99

CX LogD: 1.96

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -1.26

References

1. Guo J, Watterson SH, Spergel SH, Kempson J, Langevine CM, Shen DR, Yarde M, Cvijic ME, Banas D, Liu R, Suchard SJ, Gillooly K, Taylor T, Rex-Rabe S, Shuster DJ, McIntyre KW, Cornelius G, D'Arienzo C, Marino A, Balimane P, Salter-Cid L, McKinnon M, Barrish JC, Carter PH, Pitts WJ, Xie J, Dyckman AJ..  (2016)  Identification and synthesis of potent and selective pyridyl-isoxazole based agonists of sphingosine-1-phosphate 1 (S1P1).,  26  (10): [PMID:27055941] [10.1016/j.bmcl.2016.03.105]

2. Watterson SH, Guo J, Spergel SH, Langevine CM, Moquin RV, Shen DR, Yarde M, Cvijic ME, Banas D, Liu R, Suchard SJ, Gillooly K, Taylor T, Rex-Rabe S, Shuster DJ, McIntyre KW, Cornelius G, D'Arienzo C, Marino A, Balimane P, Warrack B, Salter-Cid L, McKinnon M, Barrish JC, Carter PH, Pitts WJ, Xie J, Dyckman AJ..  (2016)  Potent and Selective Agonists of Sphingosine 1-Phosphate 1 (S1P1): Discovery and SAR of a Novel Isoxazole Based Series.,  59  (6): [PMID:26924461] [10.1021/acs.jmedchem.6b00089]

3. Xiao HY,Watterson SH,Langevine CM,Srivastava AS,Ko SS,Zhang Y,Cherney RJ,Guo WW,Gilmore JL,Sheppeck JE,Wu DR,Li P,Ramasamy D,Arunachalam P,Mathur A,Taylor TL,Shuster DJ,McIntyre KW,Shen DR,Yarde M,Cvijic ME,Marino AM,Balimane PV,Yang Z,Banas DM,Cornelius G,D'Arienzo CJ,Warrack BM,Lehman-McKeeman L,Salter-Cid LM,Xie J,Barrish JC,Carter PH,Dyckman AJ,Dhar TG.  (2016)  Identification of Tricyclic Agonists of Sphingosine-1-phosphate Receptor 1 (S1P) Employing Ligand-Based Drug Design.,  59  (21): [PMID:27726358] [10.1021/acs.jmedchem.6b01099]

Source

Source(1):

• Scientific Literature