N-(5-((5-chloro-4-(((3R,3aR,6R,6aR)-6-methoxyhexahydrofuro[3,2-b]furan-3-yl)oxy)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)acrylamide

ID: ALA5193702

Chembl Id: CHEMBL5193702

PubChem CID: 164887513

Max Phase: Preclinical

Molecular Formula: C25H33ClN6O5

Molecular Weight: 533.03

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cc(Nc2ncc(Cl)c(O[C@@H]3CO[C@H]4[C@@H]3OC[C@H]4OC)n2)ccc1N(C)CCN(C)C

Standard InChI:  InChI=1S/C25H33ClN6O5/c1-6-21(33)29-17-11-15(7-8-18(17)32(4)10-9-31(2)3)28-25-27-12-16(26)24(30-25)37-20-14-36-22-19(34-5)13-35-23(20)22/h6-8,11-12,19-20,22-23H,1,9-10,13-14H2,2-5H3,(H,29,33)(H,27,28,30)/t19-,20-,22-,23-/m1/s1

Standard InChI Key:  MXXJXRACSRJBKS-OHUMZHCVSA-N

Alternative Forms

1. Parent:

   

   ALA5193702

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 533.03

Molecular Weight (Monoisotopic): 532.2201

AlogP: 2.56

#Rotatable Bonds: 11

Polar Surface Area: 110.31

Molecular Species: BASE

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.85

CX Basic pKa: 8.89

CX LogP: 3.09

CX LogD: 1.59

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.42

Np Likeness Score: -0.84

References

1. Li S, Si H, Song X, Lei C, He X, Wang J, Liu Y, Zhou Y, Song JG, Peng L, Tang X, Chan S, Ren X, Tu Z, Li Z, Wang Z, Zhang Z, Ding K..  (2022)  Discovery of Hexahydrofuro[3,2-b]furans as New Kinase-Selective and Orally Bioavailable JAK3 Inhibitors for the Treatment of Leukemia Harboring a JAK3 Activating Mutant.,  65  (15.0): [PMID:35860875] [10.1021/acs.jmedchem.2c00922]

Source

Source(1):

• Scientific Literature