2-[5-chloro-2-[(2,3,4,5,6-pentabromophenyl)methylcarbamoyl]phenoxy]acetic acid

ID: ALA4092708

PubChem CID: 122174240

Max Phase: Preclinical

Molecular Formula: C16H9Br5ClNO4

Molecular Weight: 714.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)COc1cc(Cl)ccc1C(=O)NCc1c(Br)c(Br)c(Br)c(Br)c1Br

Standard InChI:  InChI=1S/C16H9Br5ClNO4/c17-11-8(12(18)14(20)15(21)13(11)19)4-23-16(26)7-2-1-6(22)3-9(7)27-5-10(24)25/h1-3H,4-5H2,(H,23,26)(H,24,25)

Standard InChI Key:  QYSFXUVFRUYJCZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    9.2569  -25.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2569  -26.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5437  -25.1689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9619  -25.1689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9619  -26.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9619  -27.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6751  -28.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6751  -28.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9619  -29.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2569  -28.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2569  -28.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3842  -27.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0974  -28.0414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3842  -26.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8106  -27.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5437  -29.2755    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.5221  -28.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5174  -28.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2280  -29.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9412  -28.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9392  -28.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2280  -27.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2250  -26.8116    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.6458  -27.6278    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.6491  -29.2762    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.2269  -30.0973    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.8041  -29.2730    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
  5  6  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
  7 12  1  0
 10 16  1  0
  2  5  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 22 23  1  0
 21 24  1  0
 20 25  1  0
 19 26  1  0
 18 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092708

   ---

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: 714.22

Molecular Weight (Monoisotopic): 708.6137

AlogP: 6.55

#Rotatable Bonds: 6

Polar Surface Area: 75.63

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.90

CX Basic pKa: ┄

CX LogP: 6.54

CX LogD: 3.05

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.26

Np Likeness Score: -0.89

References

1. Endo S, Xia S, Suyama M, Morikawa Y, Oguri H, Hu D, Ao Y, Takahara S, Horino Y, Hayakawa Y, Watanabe Y, Gouda H, Hara A, Kuwata K, Toyooka N, Matsunaga T, Ikari A..  (2017)  Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.,  60  (20): [PMID:28976752] [10.1021/acs.jmedchem.7b00830]

Source

Source(1):

• Scientific Literature