8-amino-9-fluoro-7-oxo-10-(2-(pyridin-2-ylamino)ethylamino)-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1'-cyclopentane]-6-carboxylic acid

ID: ALA1834330

Chembl Id: CHEMBL1834330

PubChem CID: 25195477

Max Phase: Preclinical

Molecular Formula: C23H24FN5O4

Molecular Weight: 453.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1c(F)c(NCCNc2ccccn2)c2c3c1c(=O)c(C(=O)O)cn3C1(CCCC1)CO2

Standard InChI:  InChI=1S/C23H24FN5O4/c24-16-17(25)15-19-21(18(16)28-10-9-27-14-5-1-4-8-26-14)33-12-23(6-2-3-7-23)29(19)11-13(20(15)30)22(31)32/h1,4-5,8,11,28H,2-3,6-7,9-10,12,25H2,(H,26,27)(H,31,32)

Standard InChI Key:  WAYOWHQFYFTAPH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1834330

   8-Amino-7-fluoro-10-oxo-6-[2-(pyridin-2-ylamino)ethylamino]spiro[4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-2,1'-cyclopentane]-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: 453.47

Molecular Weight (Monoisotopic): 453.1812

AlogP: 3.00

#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: 5.83

CX Basic pKa: 6.70

CX LogP: 1.43

CX LogD: 0.88

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: -0.37

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. Seto S, Yumoto K, Okada K, Asahina Y, Iwane A, Iwago M, Terasawa R, Shreder KR, Murakami K, Kohno Y..  (2012)  Quinolone derivatives containing strained spirocycle as orally active glycogen synthase kinase 3β (GSK-3β) inhibitors for type 2 diabetics.,  20  (3): [PMID:22261023] [10.1016/j.bmc.2011.12.046]

Source

Source(1):

• Scientific Literature