8-Hydroxy-2-(4-methoxy-phenylimino)-2H-chromene-3-carboxylic acid pyridin-2-ylamide

ID: ALA2440418

PubChem CID: 72205881

Max Phase: Preclinical

Molecular Formula: C22H17N3O4

Molecular Weight: 387.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/N=c2\oc3c(O)cccc3cc2C(=O)Nc2ccccn2)cc1

Standard InChI:  InChI=1S/C22H17N3O4/c1-28-16-10-8-15(9-11-16)24-22-17(21(27)25-19-7-2-3-12-23-19)13-14-5-4-6-18(26)20(14)29-22/h2-13,26H,1H3,(H,23,25,27)/b24-22-

Standard InChI Key:  ZKNWQBUIILUEBV-GYHWCHFESA-N

Molfile:  

     RDKit          2D

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   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
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   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
   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
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   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0571  -10.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4711   -3.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7566   -4.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4711   -5.4308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1856   -5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1856   -4.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5104   -7.4776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  1 10  1  0
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  2 11  1  0
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 20 21  2  0
 16 21  1  0
 15 16  1  0
 19 22  1  0
  1 15  2  0
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 25 14  2  0
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 24 25  1  0
 26 27  2  0
 27 28  1  0
 24 28  2  0
  8 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2440418

   8-hydroxy-2-(4-methoxyphenyl)imino-N-pyridin-2-ylchromene-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: 387.40

Molecular Weight (Monoisotopic): 387.1219

AlogP: 4.03

#Rotatable Bonds: 4

Polar Surface Area: 96.95

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.23

CX Basic pKa: 3.98

CX LogP: 4.53

CX LogD: 4.53

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -1.08

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