2-Methyl-furan-3-carboxylic acid [4-({2-[4-([1,4']bipiperidinyl-1'-carbonyl)-phenoxy]-phenyl}-methyl-carbamoyl)-phenyl]-amide

ID: ALA1794053

PubChem CID: 53239961

Max Phase: Preclinical

Molecular Formula: C18H12Br2ClN3O2S

Molecular Weight: 493.18

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GW407323A | CHEMBL1794053|CHEMBL1852697|BDBM50366798|NCGC00242055-01

Canonical SMILES:  Cl.Nc1nc(-c2ccc3c(c2)C(=Cc2cc(Br)c(O)c(Br)c2)C(=O)N3)cs1

Standard InChI:  InChI=1S/C18H11Br2N3O2S.ClH/c19-12-4-8(5-13(20)16(12)24)3-11-10-6-9(15-7-26-18(21)23-15)1-2-14(10)22-17(11)25;/h1-7,24H,(H2,21,23)(H,22,25);1H

Standard InChI Key:  UBABNUZHWFXYNS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    8.3677   -0.3262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5472   -0.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9952   -0.8530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2415   -0.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3278    0.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1347    0.4745    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5271   -0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5271   -1.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8126   -2.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0981   -1.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -2.0099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8286   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0036   -1.3425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0586    0.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6106    0.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556    1.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077    2.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6527    2.9050    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.7147    1.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667    2.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9696    1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7766    0.9927    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.4176    0.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0981   -0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8126   -0.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  2  6  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  3
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 16 24  1  0
 14 25  1  0
 10 25  1  0
 25 26  2  0
  7 26  1  0
M  END

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: 493.18

Molecular Weight (Monoisotopic): 490.8939

AlogP: 5.12

#Rotatable Bonds: 2

Polar Surface Area: 88.24

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.65

CX Basic pKa: 4.07

CX LogP: 5.05

CX LogD: 4.24

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.43

Np Likeness Score: -0.62

References

1. Kakefuda A, Tsukada J, Kusayama T, Tahara A, Tsukamoto S..  (2002)  N-Methylbenzanilide derivatives as a novel class of selective V(1A) receptor antagonists.,  12  (2): [PMID:11755361] [10.1016/s0960-894x(01)00723-5]

2. Compounds: GSK PKIS; Assays: Nanosyn kinase panel,  [10.6019/CHEMBL1961873]

3. Compounds: GSK PKIS; Assays: UNC Frye lab,  [10.6019/CHEMBL2007661]

4. Data associated with the publication PLoS ONE, 8(3), e57888, (2013) PMID: 23505445. Compounds: GSK PKIS; Assays: NIH NCATS, 

Source

Source(2):

• Scientific Literature
• GSK Published Kinase Inhibitor Set