7-Hydroxy-2-(4-iodophenylimino)-2H-chromene-3-carboxylic acid pyridin-2-ylamide

ID: ALA2440426

PubChem CID: 136229867

Max Phase: Preclinical

Molecular Formula: C21H14IN3O3

Molecular Weight: 483.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccn1)c1cc2ccc(O)cc2o/c1=N\c1ccc(I)cc1

Standard InChI:  InChI=1S/C21H14IN3O3/c22-14-5-7-15(8-6-14)24-21-17(20(27)25-19-3-1-2-10-23-19)11-13-4-9-16(26)12-18(13)28-21/h1-12,26H,(H,23,25,27)/b24-21-

Standard InChI Key:  YFEMXNMSQVETGA-FLFQWRMESA-N

Molfile:  

     RDKit          2D

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   11.6335   -5.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9285   -5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2194   -5.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5104   -5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8013   -5.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8013   -6.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5104   -6.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2194   -6.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9285   -6.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3426   -5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3426   -4.2011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0475   -5.4268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7566   -5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4657   -5.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1707   -5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1707   -4.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4657   -3.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7566   -4.2011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3426   -6.6526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3426   -7.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0475   -7.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0475   -8.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3426   -9.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6335   -8.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6335   -7.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3426   -9.9255    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    8.0963   -6.6526    0.0000 O   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  1  0
  5  6  2  0
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 18 19  1  0
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 11 13  1  0
  2 11  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 20 21  1  0
 24 27  1  0
  1 20  2  0
  7 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2440426

   ---

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: 483.27

Molecular Weight (Monoisotopic): 483.0080

AlogP: 4.62

#Rotatable Bonds: 3

Polar Surface Area: 87.72

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.76

CX Basic pKa: 3.98

CX LogP: 4.97

CX LogD: 4.81

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -1.32

References

1. Endo S, Hu D, Suyama M, Matsunaga T, Sugimoto K, Matsuya Y, El-Kabbani O, Kuwata K, Hara A, Kitade Y, Toyooka N..  (2013)  Synthesis and structure-activity relationship of 2-phenyliminochromene derivatives as inhibitors for aldo-keto reductase (AKR) 1B10.,  21  (21): [PMID:24071447] [10.1016/j.bmc.2013.08.059]

Source

Source(1):

• Scientific Literature