4-(5-chloro-2-hexyl-1-methyl-1H-indole-3-carbonyl)benzoic acid

ID: ALA4090987

PubChem CID: 137644937

Max Phase: Preclinical

Molecular Formula: C23H24ClNO3

Molecular Weight: 397.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCc1c(C(=O)c2ccc(C(=O)O)cc2)c2cc(Cl)ccc2n1C

Standard InChI:  InChI=1S/C23H24ClNO3/c1-3-4-5-6-7-20-21(18-14-17(24)12-13-19(18)25(20)2)22(26)15-8-10-16(11-9-15)23(27)28/h8-14H,3-7H2,1-2H3,(H,27,28)

Standard InChI Key:  QYBXSAOPBWBEIA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    6.0547  -11.8793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5494  -11.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0808  -10.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2826  -11.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3005  -10.7970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6050  -10.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8910  -10.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8770  -11.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5732  -12.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912  -10.3464    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2912  -12.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3467   -9.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1488   -9.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8104   -9.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3664  -11.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6817  -10.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4831  -10.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7497   -9.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2087   -8.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4092   -8.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5520   -9.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0891   -9.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8169   -8.3855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7602  -11.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5772  -11.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9710  -12.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7880  -12.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1818  -13.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  1  2  1  0
  2  3  2  0
  3  5  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  7 10  1  0
  1 11  1  0
  3 12  1  0
 12 13  1  0
 12 14  2  0
  2 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 13  1  0
 21 22  1  0
 21 23  2  0
 18 21  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090987

   ---

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: 397.90

Molecular Weight (Monoisotopic): 397.1445

AlogP: 5.88

#Rotatable Bonds: 8

Polar Surface Area: 59.30

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.75

CX Basic pKa: ┄

CX LogP: 6.52

CX LogD: 3.23

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.38

Np Likeness Score: -0.33

References

1. Ye Q, Chourey S, Wang R, Chintam NR, Gravel S, Powell WS, Rokach J..  (2017)  Structure-activity relationship study of β-oxidation resistant indole-based 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) receptor antagonists.,  27  (20): [PMID:28943042] [10.1016/j.bmcl.2017.08.034]

Source

Source(1):

• Scientific Literature