2-((R)-1-((S)-2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)-isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-yl)-acetic Acid

ID: ALA4458575

Chembl Id: CHEMBL4458575

PubChem CID: 49868651

Max Phase: Preclinical

Molecular Formula: C27H25F3N4O5

Molecular Weight: 542.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@H]1CCCN(C[C@@H](O)c2ccc(-c3noc(-c4onc(-c5ccccc5)c4C(F)(F)F)n3)cc2)C1

Standard InChI:  InChI=1S/C27H25F3N4O5/c28-27(29,30)22-23(18-6-2-1-3-7-18)32-38-24(22)26-31-25(33-39-26)19-10-8-17(9-11-19)20(35)15-34-12-4-5-16(14-34)13-21(36)37/h1-3,6-11,16,20,35H,4-5,12-15H2,(H,36,37)/t16-,20-/m1/s1

Standard InChI Key:  YBQLZPRLWZZECJ-OXQOHEQNSA-N

Alternative Forms

1. Parent:

   

   ALA4458575

   (3R)-1-[(S)-2-[4-[5-[3-Phenyl-4-(trifluoromethyl)isoxazole-5-yl]-1,2,4-oxadiazole-3-yl]phenyl]-2-hydroxyethyl]piperidine-3beta-acetic 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: 542.51

Molecular Weight (Monoisotopic): 542.1777

AlogP: 5.30

#Rotatable Bonds: 8

Polar Surface Area: 125.72

Molecular Species: ZWITTERION

HBA: 8

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.83

CX Basic pKa: 9.23

CX LogP: 2.15

CX LogD: 2.15

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.31

Np Likeness Score: -1.02

References

1. Gilmore JL, Sheppeck JE, Watterson SH, Haque L, Mukhopadhyay P, Tebben AJ, Galella MA, Shen DR, Yarde M, Cvijic ME, Borowski V, Gillooly K, Taylor T, McIntyre KW, Warrack B, Levesque PC, Li JP, Cornelius G, D'Arienzo C, Marino A, Balimane P, Salter-Cid L, Barrish JC, Pitts WJ, Carter PH, Xie J, Dyckman AJ..  (2016)  Discovery and Structure-Activity Relationship (SAR) of a Series of Ethanolamine-Based Direct-Acting Agonists of Sphingosine-1-phosphate (S1P1).,  59  (13): [PMID:27309907] [10.1021/acs.jmedchem.6b00373]

2. Gilmore JL,Xiao HY,Dhar TGM,Yang MG,Xiao Z,Xie J,Lehman-McKeeman LD,Gong L,Sun H,Lecureux L,Chen C,Wu DR,Dabros M,Yang X,Taylor TL,Zhou XD,Heimrich EM,Thomas R,McIntyre KW,Borowski V,Warrack BM,Li Y,Shi H,Levesque PC,Yang Z,Marino AM,Cornelius G,D'Arienzo CJ,Mathur A,Rampulla R,Gupta A,Pragalathan B,Shen DR,Cvijic ME,Salter-Cid LM,Carter PH,Dyckman AJ.  (2019)  Identification and Preclinical Pharmacology of ((1 R,3 S)-1-Amino-3-(( S)-6-(2-methoxyphenethyl)-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopentyl)methanol (BMS-986166): A Differentiated Sphingosine-1-phosphate Receptor 1 (S1P) Modulator Advanced into Clinical Trials.,  62  (5.0): [PMID:30785748] [10.1021/acs.jmedchem.8b01695]

Source

Source(1):

• Scientific Literature