4-(4-(2-chlorobenzyloxy)-3-methoxybenzylamino)benzoic acid

ID: ALA607576

Cas Number: 701224-85-3

PubChem CID: 1290536

Max Phase: Preclinical

Molecular Formula: C22H20ClNO4

Molecular Weight: 397.86

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ZINC 01112283 | CHEMBL607576|ZINC 01112283|4-({4-[(2-chlorobenzyl)oxy]-3-methoxybenzyl}amino)benzoic acid|4-[({4-[(2-CHLOROPHENYL)METHOXY]-3-METHOXYPHENYL}METHYL)AMINO]BENZOIC ACID|BDBM50481418|4-[[4-[(2-chlorophenyl)methoxy]-3-methoxyphenyl]methylamino]benzoic acid|AKOS001087544|EN300-1192275|AN-465/41988494|Z57038584|701224-85-3

Canonical SMILES:  COc1cc(CNc2ccc(C(=O)O)cc2)ccc1OCc1ccccc1Cl

Standard InChI:  InChI=1S/C22H20ClNO4/c1-27-21-12-15(13-24-18-9-7-16(8-10-18)22(25)26)6-11-20(21)28-14-17-4-2-3-5-19(17)23/h2-12,24H,13-14H2,1H3,(H,25,26)

Standard InChI Key:  VAZCMSUVFGJUFT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.6993   -3.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0152   -4.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297   -3.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297   -2.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0152   -2.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0152   -4.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297   -5.2548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993   -5.2548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0152   -1.5423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297   -1.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297   -0.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442    0.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442    0.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297    1.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0152    0.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0152    0.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586    1.3452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586    2.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297    2.1702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0152    2.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0152    3.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993    3.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0152    5.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297    4.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993    4.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297    3.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442    3.4077    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  3  7  1  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 12  1  0
 14 18  1  0
  7  9  2  0
 18 19  1  0
  4  5  1  0
 15 20  1  0
  6 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
 22 23  2  0
 10 11  1  0
 24 25  1  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  2  0
 22 27  1  0
 23 26  1  0
 26 24  2  0
 25 27  2  0
  1  2  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA607576

   4-({4-[(2-Chlorobenzyl)oxy]-3-methoxybenzyl}amino)benzoic acid

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: 397.86

Molecular Weight (Monoisotopic): 397.1081

AlogP: 5.24

#Rotatable Bonds: 8

Polar Surface Area: 67.79

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.73

CX Basic pKa: 2.38

CX LogP: 4.84

CX LogD: 2.22

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -1.00

References

1. Podvinec M, Lim SP, Schmidt T, Scarsi M, Wen D, Sonntag LS, Sanschagrin P, Shenkin PS, Schwede T..  (2010)  Novel inhibitors of dengue virus methyltransferase: discovery by in vitro-driven virtual screening on a desktop computer grid.,  53  (4): [PMID:20108931] [10.1021/jm900776m]

Source

Source(1):

• Scientific Literature