diethyl 4,4'-(4,4'-oxybis(4,1-phenylene)bis(azanediyl))bis(4-oxobutanoate)

ID: ALA3736467

PubChem CID: 4652210

Max Phase: Preclinical

Molecular Formula: C24H28N2O7

Molecular Weight: 456.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CCC(=O)Nc1ccc(Oc2ccc(NC(=O)CCC(=O)OCC)cc2)cc1

Standard InChI:  InChI=1S/C24H28N2O7/c1-3-31-23(29)15-13-21(27)25-17-5-9-19(10-6-17)33-20-11-7-18(8-12-20)26-22(28)14-16-24(30)32-4-2/h5-12H,3-4,13-16H2,1-2H3,(H,25,27)(H,26,28)

Standard InChI Key:  IQXRIWGGSAJUPW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548    3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912    5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894    6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1872    7.5118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2296    5.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4854    8.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4837    9.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764   -7.5048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730   -8.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647   -9.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369   -7.6435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0387  -10.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470  -11.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3504  -12.7386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9891  -12.5999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586  -14.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4008  -14.8343    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
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 11 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3736467

   Ethyl 4-(4-{4-[(4-ethoxy-4-oxobutanoyl)amino]phenoxy}anilino)-4-oxobutanoate

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: 456.50

Molecular Weight (Monoisotopic): 456.1897

AlogP: 4.04

#Rotatable Bonds: 12

Polar Surface Area: 120.03

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: -0.60

References

1. Wang X, Sun C, Fang L, Yin D.  (2015)  Discovery of novel sphingosine kinase 1 inhibitors via structure-based hierarchical virtual screening,  6  (3): [10.1039/C4MD00312H]

Source

Source(1):

• Scientific Literature