4-Chloro-2-hydroxy-N-[2-(5-methyl-1H-indol-3-yl)-ethyl]-benzamide

ID: ALA4514372

PubChem CID: 155539356

Max Phase: Preclinical

Molecular Formula: C18H17ClN2O2

Molecular Weight: 328.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc2[nH]cc(CCNC(=O)c3ccc(Cl)cc3O)c2c1

Standard InChI:  InChI=1S/C18H17ClN2O2/c1-11-2-5-16-15(8-11)12(10-21-16)6-7-20-18(23)14-4-3-13(19)9-17(14)22/h2-5,8-10,21-22H,6-7H2,1H3,(H,20,23)

Standard InChI Key:  JTPINNNLYHPHNK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.6317  -16.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1737  -16.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750  -16.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892  -15.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6885  -15.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2373  -16.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9904  -15.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9071  -14.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1024  -14.6777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6968  -16.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4058  -15.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1122  -16.0859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8213  -15.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5276  -16.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8239  -14.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5219  -16.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2274  -17.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9374  -16.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9375  -16.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2314  -15.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8120  -17.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9135  -17.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6444  -17.3231    0.0000 Cl  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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
 16 21  1  0
  2 22  1  0
 18 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514372

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 328.80

Molecular Weight (Monoisotopic): 328.0979

AlogP: 3.81

#Rotatable Bonds: 4

Polar Surface Area: 65.12

Molecular Species: NEUTRAL

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.45

CX Basic pKa: ┄

CX LogP: 4.62

CX LogD: 4.35

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -0.89

References

1. Xiong R, He D, Deng X, Liu J, Lei X, Xie Z, Cao X, Chen Y, Peng J, Tang G..  (2019)  Design, synthesis and biological evaluation of tryptamine salicylic acid derivatives as potential antitumor agents.,  10  (4): [PMID:31057737] [10.1039/C8MD00484F]

Source

Source(1):

• Scientific Literature