rac-2-(7-(5-(3-cyano-5-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

ID: ALA2048293

Chembl Id: CHEMBL2048293

PubChem CID: 44138103

Max Phase: Preclinical

Molecular Formula: C23H15F3N4O4

Molecular Weight: 468.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cc(OC(F)(F)F)cc(-c2nc(-c3ccc4c(c3)cc3n4CCC3CC(=O)O)no2)c1

Standard InChI:  InChI=1S/C23H15F3N4O4/c24-23(25,26)33-17-6-12(11-27)5-16(8-17)22-28-21(29-34-22)14-1-2-18-15(7-14)9-19-13(10-20(31)32)3-4-30(18)19/h1-2,5-9,13H,3-4,10H2,(H,31,32)

Standard InChI Key:  HHVPFOZVFPAJBT-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2048293

   2-(7-(5-(3-Cyano-5-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic 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: 468.39

Molecular Weight (Monoisotopic): 468.1045

AlogP: 5.09

#Rotatable Bonds: 5

Polar Surface Area: 114.17

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.46

CX Basic pKa: ┄

CX LogP: 5.70

CX LogD: 2.84

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: -1.29

References

1. Buzard DJ, Han S, Lopez L, Kawasaki A, Moody J, Thoresen L, Ullman B, Lehmann J, Calderon I, Zhu X, Gharbaoui T, Sengupta D, Krishnan A, Gao Y, Edwards J, Barden J, Morgan M, Usmani K, Chen C, Sadeque A, Thatte J, Solomon M, Fu L, Whelan K, Liu L, Al-Shamma H, Gatlin J, Le M, Xing C, Espinola S, Jones RM..  (2012)  Fused tricyclic indoles as S1P₁ agonists with robust efficacy in animal models of autoimmune disease.,  22  (13): [PMID:22633692] [10.1016/j.bmcl.2012.04.129]

2. Buzard DJ, Han S, Lopez L, Kawasaki A, Moody J, Thoresen L, Ullman B, Lehmann J, Calderon I, Zhu X, Gharbaoui T, Sengupta D, Krishnan A, Gao Y, Edwards J, Barden J, Morgan M, Usmani K, Chen C, Sadeque A, Thatte J, Solomon M, Fu L, Whelan K, Liu L, Al-Shamma H, Gatlin J, Le M, Xing C, Espinola S, Jones RM..  (2012)  Fused tricyclic indoles as S1P₁ agonists with robust efficacy in animal models of autoimmune disease.,  22  (13): [PMID:22633692] [10.1016/j.bmcl.2012.04.129]

3. Buzard DJ, Han S, Lopez L, Kawasaki A, Moody J, Thoresen L, Ullman B, Lehmann J, Calderon I, Zhu X, Gharbaoui T, Sengupta D, Krishnan A, Gao Y, Edwards J, Barden J, Morgan M, Usmani K, Chen C, Sadeque A, Thatte J, Solomon M, Fu L, Whelan K, Liu L, Al-Shamma H, Gatlin J, Le M, Xing C, Espinola S, Jones RM..  (2012)  Fused tricyclic indoles as S1P₁ agonists with robust efficacy in animal models of autoimmune disease.,  22  (13): [PMID:22633692] [10.1016/j.bmcl.2012.04.129]

Source

Source(1):

• Scientific Literature