7-Hydroxy-2-oxo-2H-chromene-3-carboxylic Acid [3-(3,5-Difluorophenyl)propyl]amide

ID: ALA4068704

PubChem CID: 137633456

Max Phase: Preclinical

Molecular Formula: C19H15F2NO4

Molecular Weight: 359.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCCc1cc(F)cc(F)c1)c1cc2ccc(O)cc2oc1=O

Standard InChI:  InChI=1S/C19H15F2NO4/c20-13-6-11(7-14(21)9-13)2-1-5-22-18(24)16-8-12-3-4-15(23)10-17(12)26-19(16)25/h3-4,6-10,23H,1-2,5H2,(H,22,24)

Standard InChI Key:  VHBFRXWQXCNSTM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   13.3997   -8.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3985   -9.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1066   -9.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1048   -7.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8134   -8.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8122   -9.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5223   -9.5575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2382   -9.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2394   -8.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5247   -7.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9447   -9.5588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9481   -7.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6548   -8.3265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9501   -7.0990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3635   -7.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0702   -8.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7789   -7.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4856   -8.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4787   -9.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1846   -9.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8942   -9.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8936   -8.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1872   -7.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6905   -9.5522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1822  -10.3786    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.6009   -7.9237    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  8 11  2  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  2 24  1  0
 20 25  1  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4068704

   ---

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: 359.33

Molecular Weight (Monoisotopic): 359.0969

AlogP: 3.14

#Rotatable Bonds: 5

Polar Surface Area: 79.54

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.69

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -0.57

References

1. Endo S, Xia S, Suyama M, Morikawa Y, Oguri H, Hu D, Ao Y, Takahara S, Horino Y, Hayakawa Y, Watanabe Y, Gouda H, Hara A, Kuwata K, Toyooka N, Matsunaga T, Ikari A..  (2017)  Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.,  60  (20): [PMID:28976752] [10.1021/acs.jmedchem.7b00830]

Source

Source(1):

• Scientific Literature