4-methyl-(3'-hydroxy)cinnamanilide

ID: ALA2336785

PubChem CID: 71719502

Max Phase: Preclinical

Molecular Formula: C16H15NO2

Molecular Weight: 253.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)/C=C/c2cccc(O)c2)cc1

Standard InChI:  InChI=1S/C16H15NO2/c1-12-5-8-14(9-6-12)17-16(19)10-7-13-3-2-4-15(18)11-13/h2-11,18H,1H3,(H,17,19)/b10-7+

Standard InChI Key:  JYPMYOZVAOWZEW-JXMROGBWSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    8.4759  -25.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4748  -25.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1828  -26.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8925  -25.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8896  -25.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1810  -24.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5958  -24.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3050  -25.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0112  -24.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7210  -25.0503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0087  -23.8272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7681  -24.6562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4270  -24.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1326  -25.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8381  -24.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8351  -23.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1207  -23.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4181  -23.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5405  -23.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  1 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336785

   4-METHYL-(3'-HYDROXY)CINNAMANILIDE

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: 253.30

Molecular Weight (Monoisotopic): 253.1103

AlogP: 3.35

#Rotatable Bonds: 3

Polar Surface Area: 49.33

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.40

CX Basic pKa: ┄

CX LogP: 3.78

CX LogD: 3.78

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.82

Np Likeness Score: -0.55

References

1. Vishnoi S, Agrawal V, Kasana VK..  (2009)  Synthesis and structure--activity relationships of substituted cinnamic acids and amide analogues: a new class of herbicides.,  57  (8): [PMID:19368353] [10.1021/jf8034385]

2. Shi ZH, Li NG, Shi QP, Tang H, Tang YP, Li W, Yin L, Yang JP, Duan JA..  (2013)  Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors.,  23  (5): [PMID:23375794] [10.1016/j.bmcl.2013.01.027]

Source

Source(1):

• Scientific Literature