2-Allyl-7-benzyloxy-3-thioxo-2,3-dihydro-imidazo[1,5-a]indol-1-one

ID: ALA151359

PubChem CID: 44367099

Max Phase: Preclinical

Molecular Formula: C20H16N2O2S

Molecular Weight: 348.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCN1C(=O)c2cc3cc(OCc4ccccc4)ccc3n2C1=S

Standard InChI:  InChI=1S/C20H16N2O2S/c1-2-10-21-19(23)18-12-15-11-16(8-9-17(15)22(18)20(21)25)24-13-14-6-4-3-5-7-14/h2-9,11-12H,1,10,13H2

Standard InChI Key:  LYAPIAKHRGNNFE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    5.7542   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750    0.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -0.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542    0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4875    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4875    1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -1.2042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542    1.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667    1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542    1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417    1.6583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542    0.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417    2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292    2.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292    3.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167    2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042    2.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167    4.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042    3.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  4  2  0
  7  2  1  0
  8  7  1  0
  9  1  2  0
 10  7  2  0
 11  5  2  0
 12  8  2  0
 13  3  1  0
 14 13  1  0
 15 18  2  0
 16 14  2  0
 17 15  1  0
 18 10  1  0
 19 17  1  0
 20 19  1  0
 21 20  2  0
 22 20  1  0
 23 22  2  0
 24 21  1  0
 25 23  1  0
  4  5  1  0
  8  6  1  0
 15 12  1  0
 25 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA151359

   6-Phenylmethoxy-2-prop-2-enyl-1-sulfanylideneimidazo[1,5-a]indol-3-one

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: 348.43

Molecular Weight (Monoisotopic): 348.0932

AlogP: 4.00

#Rotatable Bonds: 5

Polar Surface Area: 34.47

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.26

CX LogD: 4.26

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.52

Np Likeness Score: -0.95

References

1. Voss ME, Carter PH, Tebben AJ, Scherle PA, Brown GD, Thompson LA, Xu M, Lo YC, Yang G, Liu RQ, Strzemienski P, Everlof JG, Trzaskos JM, Decicco CP..  (2003)  Both 5-arylidene-2-thioxodihydropyrimidine-4,6(1H,5H)-diones and 3-thioxo-2,3-dihydro-1H-imidazo[1,5-a]indol-1-ones are light-dependent tumor necrosis factor-alpha antagonists.,  13  (3): [PMID:12565966] [10.1016/s0960-894x(02)00941-1]

Source

Source(1):

• Scientific Literature