N-(3,4-Dichloro-phenyl)-2-((5aS,11bS)-2-oxo-5a,11b-dihydro-5H,6H-7-oxa-1,4-dithia-3-aza-cyclopenta[c]phenanthren-3-yl)-acetamide

ID: ALA4174740

PubChem CID: 1994107

Max Phase: Preclinical

Molecular Formula: C21H16Cl2N2O3S2

Molecular Weight: 479.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cn1c2c(sc1=O)[C@@H]1c3ccccc3OC[C@H]1CS2)Nc1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C21H16Cl2N2O3S2/c22-14-6-5-12(7-15(14)23)24-17(26)8-25-20-19(30-21(25)27)18-11(10-29-20)9-28-16-4-2-1-3-13(16)18/h1-7,11,18H,8-10H2,(H,24,26)/t11-,18-/m0/s1

Standard InChI Key:  QDEZDVNUPRLWTD-VOJFVSQTSA-N

Molfile:  

     RDKit          2D

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    4.4392   -9.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1547  -10.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8718   -9.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8690   -8.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4404   -8.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504   -8.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7334   -7.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7311   -8.5695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4434   -7.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1490   -7.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1539   -6.1201    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4428   -6.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8595   -6.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8566   -7.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6294   -7.5986    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1097   -6.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6339   -6.2826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7244   -6.9234    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599   -8.1621    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9355   -6.9449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8916   -5.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7000   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9579   -4.5446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2505   -5.9447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7662   -4.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3154   -4.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1230   -4.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3816   -4.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8263   -3.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0207   -3.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0814   -2.6370    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.1897   -3.8693    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  2  0
  5  6  1  0
  5  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  1  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  9 18  1  6
 10 19  1  1
 16 20  2  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 29 31  1  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4174740

   N-(3,4-dichlorophenyl)-2-[(1S,10S)-15-oxo-8-oxa-12,16-dithia-14-azatetracyclo[8.7.0.02,7.013,17]heptadeca-2,4,6,13(17)-tetraen-14-yl]acetamide

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: 479.41

Molecular Weight (Monoisotopic): 477.9979

AlogP: 5.10

#Rotatable Bonds: 3

Polar Surface Area: 60.33

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.23

CX Basic pKa: ┄

CX LogP: 4.80

CX LogD: 4.80

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -1.23

References

1. Szychowski KA, Leja ML, Kaminskyy DV, Kryshchyshyn AP, Binduga UE, Pinyazhko OR, Lesyk RB, Tobiasz J, Gmiński J..  (2017)  Anticancer properties of 4-thiazolidinone derivatives depend on peroxisome proliferator-activated receptor gamma (PPARγ).,  141  [PMID:29031063] [10.1016/j.ejmech.2017.09.071]

Source

Source(1):

• Scientific Literature