(R)-1-tert-butyl-N-(8-(2-(1-methyl-1H-pyrazol-4-ylamino)pyrimidin-4-yl)-2-(oxetan-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-yl)-1H-1,2,3-triazole-4-carboxamide

ID: ALA5083772

Chembl Id: CHEMBL5083772

PubChem CID: 135355941

Max Phase: Phase

Molecular Formula: C28H34N10O2

Molecular Weight: 542.65

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Biib-091 | Biib091

Canonical SMILES:  Cn1cc(Nc2nccc(-c3ccc4c(c3)CN(C3COC3)CC[C@H]4NC(=O)c3cn(C(C)(C)C)nn3)n2)cn1

Standard InChI:  InChI=1S/C28H34N10O2/c1-28(2,3)38-15-25(34-35-38)26(39)32-24-8-10-37(21-16-40-17-21)13-19-11-18(5-6-22(19)24)23-7-9-29-27(33-23)31-20-12-30-36(4)14-20/h5-7,9,11-12,14-15,21,24H,8,10,13,16-17H2,1-4H3,(H,32,39)(H,29,31,33)/t24-/m1/s1

Standard InChI Key:  JSAQBOQCZJHWMA-XMMPIXPASA-N

Alternative Forms

1. Parent:

   

   ALA5083772

   BIIB-091

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 542.65

Molecular Weight (Monoisotopic): 542.2866

AlogP: 3.04

#Rotatable Bonds: 6

Polar Surface Area: 127.91

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.66

CX Basic pKa: 6.78

CX LogP: 2.65

CX LogD: 2.55

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.38

Np Likeness Score: -1.45

References

1. Hopkins BT, Bame E, Bajrami B, Black C, Bohnert T, Boiselle C, Burdette D, Burns JC, Delva L, Donaldson D, Grater R, Gu C, Hoemberger M, Johnson J, Kapadnis S, King K, Lulla M, Ma B, Marx I, Magee T, Meissner R, Metrick CM, Mingueneau M, Murugan P, Otipoby KL, Polack E, Poreci U, Prince R, Roach AM, Rowbottom C, Santoro JC, Schroeder P, Tang H, Tien E, Zhang F, Lyssikatos J..  (2022)  Discovery and Preclinical Characterization of BIIB091, a Reversible, Selective BTK Inhibitor for the Treatment of Multiple Sclerosis.,  65  (2.0): [PMID:34734694] [10.1021/acs.jmedchem.1c00926]

2. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Clinical Candidates