(S)-8-amino-9-fluoro-3-methyl-7-oxo-10-(3-(pyridin-2-yl)propylamino)-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carbonitrile

ID: ALA1940990

Chembl Id: CHEMBL1940990

PubChem CID: 56945119

Max Phase: Preclinical

Molecular Formula: C21H20FN5O2

Molecular Weight: 393.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1COc2c(NCCCc3ccccn3)c(F)c(N)c3c(=O)c(C#N)cn1c23

Standard InChI:  InChI=1S/C21H20FN5O2/c1-12-11-29-21-18(26-8-4-6-14-5-2-3-7-25-14)16(22)17(24)15-19(21)27(12)10-13(9-23)20(15)28/h2-3,5,7,10,12,26H,4,6,8,11,24H2,1H3/t12-/m0/s1

Standard InChI Key:  ZGPDFKYQHBHSHB-LBPRGKRZSA-N

Alternative Forms

1. Parent:

   

   ALA1940990

   (2S)-8-amino-7-fluoro-2-methyl-10-oxo-6-(3-pyridin-2-ylpropylamino)-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carbonitrile

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: 393.42

Molecular Weight (Monoisotopic): 393.1601

AlogP: 2.99

#Rotatable Bonds: 5

Polar Surface Area: 105.96

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.59

CX LogP: 2.24

CX LogD: 2.23

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -0.93

References

1. Li B, Cociorva OM, Nomanbhoy T, Li Q, Nakamura K, Nomura M, Okada K, Yumoto K, Liyanage M, Zhang MC, Aban A, Szardenings AK, Kozarich JW, Kohno Y, Shreder KR..  (2012)  6-Position optimization of tricyclic 4-quinolone-based inhibitors of glycogen synthase kinase-3β: discovery of nitrile derivatives with picomolar potency.,  22  (2): [PMID:22202172] [10.1016/j.bmcl.2011.12.006]

Source

Source(1):

• Scientific Literature