Thiopropazate

ID: ALA1697851

Cas Number: 84-06-0

PubChem CID: 6762

Max Phase: Approved

Molecular Formula: C23H28ClN3O2S

Molecular Weight: 446.02

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(3): Thiopropazate hydrochloride | Thiopropazate dihydrochloride | Dartalan

Canonical SMILES:  CC(=O)OCCN1CCN(CCCN2c3ccccc3Sc3ccc(Cl)cc32)CC1

Standard InChI:  InChI=1S/C23H28ClN3O2S/c1-18(28)29-16-15-26-13-11-25(12-14-26)9-4-10-27-20-5-2-3-6-22(20)30-23-8-7-19(24)17-21(23)27/h2-3,5-8,17H,4,9-16H2,1H3

Standard InChI Key:  AIUHRQHVWSUTGJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    3.2375   -6.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -7.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -7.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -7.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750   -6.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625   -5.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -4.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750   -7.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5417   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -4.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -4.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -5.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1375   -4.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -7.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -6.1917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -4.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0292   -6.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0292   -7.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7125   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -6.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -7.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  1  1  0
  5  2  2  0
  6  4  2  0
  7  2  1  0
  8 23  1  0
  9 15  1  0
 10 20  1  0
 11  5  1  0
 12 10  2  0
 13  1  1  0
 14  7  2  0
 15 17  1  0
 16  8  1  0
 17  8  1  0
 18 16  1  0
 19 13  1  0
 20 26  1  0
 21 14  1  0
 22 14  1  0
 23 19  1  0
 24  9  1  0
 25  4  1  0
 26 24  1  0
 27  6  1  0
 28 10  1  0
 29 25  2  0
 30 29  1  0
  5  3  1  0
 27 30  2  0
 11 21  2  0
 18  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1697851

   THIOPROPAZATE

2. Alternative Forms:

   

   ALA1697851

   THIOPROPAZATE HYDROCHLORIDE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 446.02

Molecular Weight (Monoisotopic): 445.1591

AlogP: 4.51

#Rotatable Bonds: 7

Polar Surface Area: 36.02

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.50

CX LogP: 4.13

CX LogD: 3.78

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.58

Np Likeness Score: -1.08

References

1. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

2. WHO Anatomical Therapeutic Chemical Classification, 

3. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(3):

• Scientific Literature
• WHO Anatomical Therapeutic Chemical Classification
• IMI-CARE SARS-CoV-2 Data