2-Oxo-2H-chromene-3-carboxylic Acid [3-(4-Hydroxyphenyl)-propyl]amide

ID: ALA4092206

PubChem CID: 110667198

Max Phase: Preclinical

Molecular Formula: C19H17NO4

Molecular Weight: 323.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCCc1ccc(O)cc1)c1cc2ccccc2oc1=O

Standard InChI:  InChI=1S/C19H17NO4/c21-15-9-7-13(8-10-15)4-3-11-20-18(22)16-12-14-5-1-2-6-17(14)24-19(16)23/h1-2,5-10,12,21H,3-4,11H2,(H,20,22)

Standard InChI Key:  YSSVZZNDRWDQQF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   14.2664  -13.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2653  -13.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9733  -14.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9715  -12.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6801  -13.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6790  -13.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3891  -14.3657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1049  -13.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1061  -13.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3914  -12.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8114  -14.3670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8148  -12.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5215  -13.1347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8168  -11.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2302  -12.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9369  -13.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6456  -12.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3523  -13.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3454  -13.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0513  -14.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7610  -13.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7603  -13.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0539  -12.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4682  -14.3721    0.0000 O   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
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092206

   N-[3-(4-hydroxyphenyl)propyl]-2-oxochromene-3-carboxamide

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: 323.35

Molecular Weight (Monoisotopic): 323.1158

AlogP: 2.86

#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: 9.51

CX Basic pKa: ┄

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.56

Np Likeness Score: -0.48

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