5-(5-Benzyloxy-1H-indol-3-ylmethylene)-1,3-diethyl-2-thioxo-dihydro-pyrimidine-4,6-dione

ID: ALA150992

PubChem CID: 135921196

Max Phase: Preclinical

Molecular Formula: C24H23N3O3S

Molecular Weight: 433.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)C(=Cc2c[nH]c3ccc(OCc4ccccc4)cc23)C(=O)N(CC)C1=S

Standard InChI:  InChI=1S/C24H23N3O3S/c1-3-26-22(28)20(23(29)27(4-2)24(26)31)12-17-14-25-21-11-10-18(13-19(17)21)30-15-16-8-6-5-7-9-16/h5-14,25H,3-4,15H2,1-2H3

Standard InChI Key:  FAIXVGXVZWCCOR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.7792   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9500   -1.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1417   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4917   -1.9292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   14.0500    1.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3875    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8542    1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0875    2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8917    2.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5292    3.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5917   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7500   -0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7542    3.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1292    3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5667    4.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
 13 10  1  0
 22 19  2  0
 31 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA150992

   ---

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: 433.53

Molecular Weight (Monoisotopic): 433.1460

AlogP: 4.13

#Rotatable Bonds: 6

Polar Surface Area: 65.64

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.50

CX LogD: 4.50

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: -0.90

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