sodium 2-tert-butoxy-2-(3-(4-methoxyphenyl)-1-methyl-1H-indol-2-yl)acetate

ID: ALA4532605

PubChem CID: 155547190

Max Phase: Preclinical

Molecular Formula: C22H24NNaO4

Molecular Weight: 367.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2c(C(OC(C)(C)C)C(=O)[O-])n(C)c3ccccc23)cc1.[Na+]

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

Standard InChI Key:  WRCYZJHZKMJYRO-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    6.8803  -11.1699    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    3.7476  -10.9314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355  -10.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7507   -9.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9635  -10.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9673   -9.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2543   -9.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5369   -9.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5371  -10.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2507  -11.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0604  -10.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4705  -10.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754   -9.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3004   -9.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154   -8.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7104  -10.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1249   -9.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0555  -11.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2955  -10.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000  -11.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0046   -8.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8134   -8.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702   -7.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5194   -7.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -7.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4554   -8.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7751   -6.4612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5823   -6.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  3 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 12 18  2  0
 12 19  1  0
  2 20  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  4 21  1  0
 24 27  1  0
 27 28  1  0
M  CHG  2   1   1  19  -1
M  END

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: 4.79

#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: 4.01

CX Basic pKa: ┄

CX LogP: 4.32

CX LogD: 1.17

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -0.17

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