2-tert-butoxy-2-(1-(4-methoxyphenyl)-3-methyl-1H-indol-2-yl)acetic acid

ID: ALA4513790

PubChem CID: 155539121

Max Phase: Preclinical

Molecular Formula: C22H25NO4

Molecular Weight: 367.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(-n2c(C(OC(C)(C)C)C(=O)O)c(C)c3ccccc32)cc1

Standard InChI:  InChI=1S/C22H25NO4/c1-14-17-8-6-7-9-18(17)23(15-10-12-16(26-5)13-11-15)19(14)20(21(24)25)27-22(2,3)4/h6-13,20H,1-5H3,(H,24,25)

Standard InChI Key:  PDVIKDBXKUUQAM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   21.2694   -6.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7527   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2725   -4.8697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4927   -5.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4966   -5.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7903   -4.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0797   -5.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0798   -5.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7867   -6.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5699   -5.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9760   -6.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9809   -4.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7981   -4.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2091   -4.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2042   -5.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6148   -4.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5650   -6.9523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7932   -6.2489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5240   -4.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3251   -3.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5795   -3.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0339   -2.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2306   -2.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9799   -3.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2872   -1.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0867   -1.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5194   -6.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  1  2  2  0
  2  3  1  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
  2 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 11 17  2  0
 11 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  3 19  1  0
 22 25  1  0
 25 26  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513790

   ---

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: 367.45

Molecular Weight (Monoisotopic): 367.1784

AlogP: 4.89

#Rotatable Bonds: 5

Polar Surface Area: 60.69

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.95

CX Basic pKa: ┄

CX LogP: 4.85

CX LogD: 1.66

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -0.51

References

1. Patel PA, Kvaratskhelia N, Mansour Y, Antwi J, Feng L, Koneru P, Kobe MJ, Jena N, Shi G, Mohamed MS, Li C, Kessl JJ, Fuchs JR..  (2016)  Indole-based allosteric inhibitors of HIV-1 integrase.,  26  (19): [PMID:27568085] [10.1016/j.bmcl.2016.08.037]

Source

Source(1):

• Scientific Literature