(2S,2'S,5S,5'S)-3,3'-(4,4'-(ethane-1,2-diyl)bis(4,1-phenylene))bis(2-(4-methoxyphenyl)-5-methylthiazolidin-4-one)

ID: ALA2268794

PubChem CID: 11250599

Max Phase: Preclinical

Molecular Formula: C36H36N2O4S2

Molecular Weight: 624.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc([C@@H]2S[C@@H](C)C(=O)N2c2ccc(CCc3ccc(N4C(=O)[C@H](C)S[C@H]4c4ccc(OC)cc4)cc3)cc2)cc1

Standard InChI:  InChI=1S/C36H36N2O4S2/c1-23-33(39)37(35(43-23)27-11-19-31(41-3)20-12-27)29-15-7-25(8-16-29)5-6-26-9-17-30(18-10-26)38-34(40)24(2)44-36(38)28-13-21-32(42-4)22-14-28/h7-24,35-36H,5-6H2,1-4H3/t23-,24-,35-,36-/m0/s1

Standard InChI Key:  NZXKMBYOABFFEY-ZRERGLNCSA-N

Molfile:  

     RDKit          2D

 44 49  0  0  0  0  0  0  0  0999 V2000
   18.1304   -3.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7173   -4.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1193   -4.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9343   -4.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3456   -4.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9412   -3.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9001   -4.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1628   -4.0981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6457   -4.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4235   -4.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4257   -3.6928    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.6491   -3.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3927   -5.5376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4002   -2.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9506   -2.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7022   -1.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9029   -1.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3524   -1.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6036   -2.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2622   -4.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6667   -3.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2562   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4412   -2.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0385   -3.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4514   -4.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4839   -3.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2213   -3.4081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7305   -2.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9557   -3.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9634   -3.8287    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7430   -4.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9740   -1.9715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0013   -4.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4583   -5.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7160   -6.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5173   -6.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0605   -5.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7999   -5.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7767   -7.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2352   -7.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6530   -0.3293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2018    0.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2900   -2.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0834   -4.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  9 13  2  0
 12 14  1  6
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 21 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 27  1  0
 28 32  2  0
 31 33  1  6
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 33  1  0
 26  7  1  0
 36 39  1  0
 39 40  1  0
 17 41  1  0
 41 42  1  0
 29 43  1  1
 10 44  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2268794

   (2S,5S)-2-(4-methoxyphenyl)-3-[4-[2-[4-[(2S,5S)-2-(4-methoxyphenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]phenyl]ethyl]phenyl]-5-methyl-1,3-thiazolidin-4-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: 624.83

Molecular Weight (Monoisotopic): 624.2116

AlogP: 7.82

#Rotatable Bonds: 9

Polar Surface Area: 59.08

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.74

CX LogD: 7.74

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.19

Np Likeness Score: -0.23

References

1. Siddiqui IR, Singh PK, Singh J, Singh J..  (2003)  Synthesis and fungicidal activity of novel 4,4'-bis(2' '-aryl-5' '-methyl/unsubstituted-4' '-oxo-thiazolidin-3' '-yl) bibenzyl.,  51  (24): [PMID:14611172] [10.1021/jf0342324]

Source

Source(1):

• Scientific Literature