1,2-bis[3,5-bis(3,4-Dimethoxybenzylidene)-4-oxo-piperidin-1-yl]ethane-1,2-dione

ID: ALA2391209

PubChem CID: 71699612

Max Phase: Preclinical

Molecular Formula: C48H48N2O12

Molecular Weight: 844.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2\CN(C(=O)C(=O)N3C/C(=C\c4ccc(OC)c(OC)c4)C(=O)/C(=C/c4ccc(OC)c(OC)c4)C3)C/C(=C\c3ccc(OC)c(OC)c3)C2=O)cc1OC

Standard InChI:  InChI=1S/C48H48N2O12/c1-55-37-13-9-29(21-41(37)59-5)17-33-25-49(26-34(45(33)51)18-30-10-14-38(56-2)42(22-30)60-6)47(53)48(54)50-27-35(19-31-11-15-39(57-3)43(23-31)61-7)46(52)36(28-50)20-32-12-16-40(58-4)44(24-32)62-8/h9-24H,25-28H2,1-8H3/b33-17+,34-18+,35-19+,36-20+

Standard InChI Key:  HTNXCRNOCCJJPS-XRQSTUJTSA-N

Molfile:  

     RDKit          2D

 62 67  0  0  0  0  0  0  0  0999 V2000
   29.1388  -10.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8413  -10.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4253  -10.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8421  -11.7930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1379  -12.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1457  -13.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8576  -13.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5617  -13.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5540  -12.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8653  -14.2481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2722  -13.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9729  -12.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9624  -12.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6652  -11.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3784  -12.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3889  -12.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6861  -13.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4415  -13.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7289  -13.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7284  -12.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0191  -11.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3144  -12.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3148  -13.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0200  -13.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1476   -9.7493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8610   -9.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8719   -8.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1694   -8.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4559   -8.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4450   -9.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1802   -7.2944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7533   -8.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0399   -8.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3373   -8.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6260   -8.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6151   -9.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3177   -9.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0311   -9.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5854   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2918   -8.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3054   -9.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0201   -9.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7213   -9.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7078   -8.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9930   -8.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5514  -10.5770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9022   -9.6949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1998   -9.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6061  -11.8055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4355   -9.7169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1366   -9.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0806  -11.7431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7937  -12.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8990  -12.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3078  -10.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5952  -10.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0326  -10.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3313  -10.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1021  -13.3782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1133  -14.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6070  -13.4386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8994  -13.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  4  9  1  0
  7 10  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
  8 11  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
  6 18  2  0
  2  4  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 25 30  1  0
 28 31  2  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 33 38  2  0
 29 32  2  0
 39 40  1  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
 40 45  2  0
 27 39  2  0
  1 25  1  0
  2 46  2  0
 36 47  1  0
 47 48  1  0
 22 49  1  0
 43 50  1  0
 50 51  1  0
 15 52  1  0
 52 53  1  0
 49 54  1  0
 37 55  1  0
 55 56  1  0
 42 57  1  0
 57 58  1  0
 16 59  1  0
 59 60  1  0
 23 61  1  0
 61 62  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2391209

   1,2-bis[(3E,5E)-3,5-bis[(3,4-dimethoxyphenyl)methylidene]-4-oxopiperidin-1-yl]ethane-1,2-dione

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: 844.91

Molecular Weight (Monoisotopic): 844.3207

AlogP: 6.21

#Rotatable Bonds: 12

Polar Surface Area: 148.60

Molecular Species: NEUTRAL

HBA: 12

HBD: ┄

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.94

CX LogD: 5.94

Aromatic Rings: 4

Heavy Atoms: 62

QED Weighted: 0.12

Np Likeness Score: -0.11

References

1. Das S, Das U, Michel D, Gorecki DK, Dimmock JR..  (2013)  Novel 3,5-bis(arylidene)-4-piperidone dimers: potent cytotoxins against colon cancer cells.,  64  [PMID:23644215] [10.1016/j.ejmech.2013.03.055]

2. Santiago-Vazquez Y, Das S, Das U, Robles-Escajeda E, Ortega NM, Lema C, Varela-Ramírez A, Aguilera RJ, Balzarini J, De Clercq E, Dimmock SG, Gorecki DK, Dimmock JR..  (2014)  Novel 3,5-bis(arylidene)-4-oxo-1-piperidinyl dimers: structure-activity relationships and potent antileukemic and antilymphoma cytotoxicity.,  77  [PMID:24657568] [10.1016/j.ejmech.2014.03.009]

Source

Source(1):

• Scientific Literature