4-methyl-(4'-hydroxy)cinnamanilide

ID: ALA2336346

PubChem CID: 71716445

Max Phase: Preclinical

Molecular Formula: C16H15NO2

Molecular Weight: 253.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)/C=C/c2ccc(O)cc2)cc1

Standard InChI:  InChI=1S/C16H15NO2/c1-12-2-7-14(8-3-12)17-16(19)11-6-13-4-9-15(18)10-5-13/h2-11,18H,1H3,(H,17,19)/b11-6+

Standard InChI Key:  JKPCWPAVEKIDRM-IZZDOVSWSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   28.2123   -8.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2112   -9.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9192  -10.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6289   -9.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6260   -8.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9174   -8.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3322   -8.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0415   -8.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7476   -8.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4575   -8.7890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7451   -7.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1634   -8.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8690   -8.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5745   -8.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5715   -7.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8571   -7.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1545   -7.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5031  -10.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2769   -7.1439    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
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  2 18  1  0
 15 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336346

   4-METHYL-(4'-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: 9.42

CX Basic pKa: ┄

CX LogP: 3.78

CX LogD: 3.78

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.82

Np Likeness Score: -0.52

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