1-[4-(3-{1-[4-(2-Amino-pyrimidin-5-yl)-phenyl]-cyclobutyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-2-methyl-propan-2-ol

ID: ALA3417511

Chembl Id: CHEMBL3417511

PubChem CID: 68075088

Max Phase: Preclinical

Molecular Formula: C23H25N7O2

Molecular Weight: 431.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O)Cn1cc(-c2nc(C3(c4ccc(-c5cnc(N)nc5)cc4)CCC3)no2)cn1

Standard InChI:  InChI=1S/C23H25N7O2/c1-22(2,31)14-30-13-17(12-27-30)19-28-20(29-32-19)23(8-3-9-23)18-6-4-15(5-7-18)16-10-25-21(24)26-11-16/h4-7,10-13,31H,3,8-9,14H2,1-2H3,(H2,24,25,26)

Standard InChI Key:  YMEFXAYUHCDQHO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3417511

   1-[4-[3-[1-[4-(2-Aminopyrimidin-5-yl)phenyl]cyclobutyl]-1,2,4-oxadiazol-5-yl]pyrazol-1-yl]-2-methylpropan-2-ol

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: 431.50

Molecular Weight (Monoisotopic): 431.2070

AlogP: 3.21

#Rotatable Bonds: 6

Polar Surface Area: 128.77

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.16

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.48

Np Likeness Score: -0.80

References

1. Takahashi H, Riether D, Bartolozzi A, Bosanac T, Berger V, Binetti R, Broadwater J, Chen Z, Crux R, De Lombaert S, Dave R, Dines JA, Fadra-Khan T, Flegg A, Garrigou M, Hao MH, Huber J, Hutzler JM, Kerr S, Kotey A, Liu W, Lo HY, Loke PL, Mahaney PE, Morwick TM, Napier S, Olague A, Pack E, Padyana AK, Thomson DS, Tye H, Wu L, Zindell RM, Abeywardane A, Simpson T..  (2015)  Synthesis, SAR, and series evolution of novel oxadiazole-containing 5-lipoxygenase activating protein inhibitors: discovery of 2-[4-(3-{(r)-1-[4-(2-amino-pyrimidin-5-yl)-phenyl]-1-cyclopropyl-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-N,N-dimethyl-acetamide (BI 665915).,  58  (4): [PMID:25671290] [10.1021/jm501185j]

2. Bartolozzi A, Abeywardane A, Bosanac T, Broadwater JA, Chen Z, Hutzler JM, Huber JD, Nemoto P, Olague A, Riether D, Simpson T, Takahashi H, Wu L, Zhang Y, Zindell RM..  (2017)  Discovery and optimization of oxadiazole-based FLAP inhibitors.,  27  (20): [PMID:28927794] [10.1016/j.bmcl.2017.09.007]

Source

Source(1):

• Scientific Literature