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

ID: ALA2268796

PubChem CID: 11445349

Max Phase: Preclinical

Molecular Formula: C38H40N2O6S2

Molecular Weight: 684.88

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)c(OC)c4)cc3)cc2)cc1OC

Standard InChI:  InChI=1S/C38H40N2O6S2/c1-23-35(41)39(37(47-23)27-13-19-31(43-3)33(21-27)45-5)29-15-9-25(10-16-29)7-8-26-11-17-30(18-12-26)40-36(42)24(2)48-38(40)28-14-20-32(44-4)34(22-28)46-6/h9-24,37-38H,7-8H2,1-6H3/t23-,24-,37-,38-/m0/s1

Standard InChI Key:  XKLMJHQMYXPXON-XWDGWKTRSA-N

Molfile:  

     RDKit          2D

 48 53  0  0  0  0  0  0  0  0999 V2000
    6.7805   -9.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3674  -10.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7695  -10.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5845  -10.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9957  -10.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5913   -9.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5502  -10.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8129  -10.0331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2958  -10.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0737  -10.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0758   -9.6277    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2993   -9.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0429  -11.4725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0504   -8.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6007   -7.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3523   -7.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5531   -7.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0025   -7.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2538   -8.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9123  -10.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169   -9.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063   -8.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0913   -8.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6886   -9.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1015  -10.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1340   -9.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8714   -9.3431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3806   -8.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6058   -8.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6136   -9.7637    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3931  -10.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241   -7.9065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514  -10.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1084  -11.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3661  -12.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1675  -12.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106  -11.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500  -10.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117  -11.8754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7727  -12.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4268  -13.1054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853  -13.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9023   -6.6121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7007   -6.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3031   -6.2643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8520   -5.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0598   -8.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7335  -10.9270    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
 37 39  1  0
 39 40  1  0
 36 41  1  0
 41 42  1  0
 16 43  1  0
 43 44  1  0
 17 45  1  0
 45 46  1  0
 29 47  1  1
 10 48  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2268796

   (2S,5S)-2-(3,4-dimethoxyphenyl)-3-[4-[2-[4-[(2S,5S)-2-(3,4-dimethoxyphenyl)-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: 684.88

Molecular Weight (Monoisotopic): 684.2328

AlogP: 7.84

#Rotatable Bonds: 11

Polar Surface Area: 77.54

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.43

CX LogD: 7.43

Aromatic Rings: 4

Heavy Atoms: 48

QED Weighted: 0.16

Np Likeness Score: -0.16

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