1-(3,4-dichlorobenzyl)-4-fluoro-5-hydroxy-1H-indole-2-carboxylic acid

ID: ALA4092536

PubChem CID: 9928514

Max Phase: Preclinical

Molecular Formula: C16H10Cl2FNO3

Molecular Weight: 354.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c(F)c(O)ccc2n1Cc1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C16H10Cl2FNO3/c17-10-2-1-8(5-11(10)18)7-20-12-3-4-14(21)15(19)9(12)6-13(20)16(22)23/h1-6,21H,7H2,(H,22,23)

Standard InChI Key:  XVJRJCHFAPOINJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   24.1068   -7.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5553   -6.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8113   -5.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2556   -5.2090    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.6148   -5.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8708   -4.8686    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.1664   -6.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9102   -7.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4660   -7.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2100   -8.4441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4259   -8.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7130   -8.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9961   -8.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9961   -9.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2831   -9.9356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7130   -9.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7130  -10.7607    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.4259   -9.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2100   -9.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6947   -9.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5198   -9.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9303   -8.3977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9303   -9.8234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  1  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 11 18  2  0
 18 19  1  0
 19 20  2  0
 10 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092536

   1-[(3,4-Dichlorophenyl)methyl]-4-fluoro-5-hydroxyindole-2-carboxylic 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: 354.16

Molecular Weight (Monoisotopic): 353.0022

AlogP: 4.54

#Rotatable Bonds: 3

Polar Surface Area: 62.46

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.39

CX Basic pKa: ┄

CX LogP: 4.64

CX LogD: 1.11

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.73

Np Likeness Score: -1.17

References

1. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

Source

Source(1):

• Scientific Literature