(S)-8-amino-9-fluoro-3-methyl-7-oxo-10-(2-(pyridin-2-ylamino)ethylamino)-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

ID: ALA1834323

Chembl Id: CHEMBL1834323

PubChem CID: 53484135

Max Phase: Preclinical

Molecular Formula: C20H20FN5O4

Molecular Weight: 413.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1COc2c(NCCNc3ccccn3)c(F)c(N)c3c(=O)c(C(=O)O)cn1c23

Standard InChI:  InChI=1S/C20H20FN5O4/c1-10-9-30-19-16(25-7-6-24-12-4-2-3-5-23-12)14(21)15(22)13-17(19)26(10)8-11(18(13)27)20(28)29/h2-5,8,10,25H,6-7,9,22H2,1H3,(H,23,24)(H,28,29)/t10-/m0/s1

Standard InChI Key:  BEOOHAUYYYZCER-JTQLQIEISA-N

Alternative Forms

1. Parent:

   

   ALA1834323

   (2S)-8-amino-7-fluoro-2-methyl-10-oxo-6-[2-(pyridin-2-ylamino)ethylamino]-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

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: 413.41

Molecular Weight (Monoisotopic): 413.1499

AlogP: 2.29

#Rotatable Bonds: 6

Polar Surface Area: 131.50

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.70

CX Basic pKa: 6.68

CX LogP: 0.49

CX LogD: -0.11

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -0.51

References

1. Cociorva OM, Li B, Nomanbhoy T, Li Q, Nakamura A, Nakamura K, Nomura M, Okada K, Seto S, Yumoto K, Liyanage M, Zhang MC, Aban A, Leen B, Szardenings AK, Rosenblum JS, Kozarich JW, Kohno Y, Shreder KR..  (2011)  Synthesis and structure-activity relationship of 4-quinolone-3-carboxylic acid based inhibitors of glycogen synthase kinase-3β.,  21  (19): [PMID:21873061] [10.1016/j.bmcl.2011.07.073]

2. 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