1-[2-(3-Diethylamino-2-hydroxy-propoxy)-phenyl]-3-phenyl-propan-1-one

ID: ALA93496

PubChem CID: 2856987

Max Phase: Preclinical

Molecular Formula: C22H29NO3

Molecular Weight: 355.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SJ000150489 | CHEMBL93496|1-{2-[3-(diethylamino)-2-hydroxypropoxy]phenyl}-3-phenylpropan-1-one|MLS000107538|1-(2-(3-(diethylamino)-2-hydroxypropoxy)phenyl)-3-phenylpropan-1-one|CBMicro_026350|SCHEMBL1331282|HMS2487J21|BDBM50134982|AKOS003377641|AKOS022066752|SMR000111904|BIM-0026533.P001|SJ000150489|1-[2-(3-Diethylamino-2-hydroxy-propoxy)-phenyl]-3-phenyl-propan-1-one|1-(2-(3-(diethylamino)-2-hydroxypropoxy)phenyl)-3-phenylpropan-1-one | 1-{2-[3-(diethylamino)-2-hydroxypropoxy]phenyl}-3-phenylprShow More⌵

Canonical SMILES:  CCN(CC)CC(O)COc1ccccc1C(=O)CCc1ccccc1

Standard InChI:  InChI=1S/C22H29NO3/c1-3-23(4-2)16-19(24)17-26-22-13-9-8-12-20(22)21(25)15-14-18-10-6-5-7-11-18/h5-13,19,24H,3-4,14-17H2,1-2H3

Standard InChI Key:  XBYIRYDJOVXGAL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   11.0194   -7.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0182   -8.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7331   -8.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4495   -8.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4466   -7.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7313   -6.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1596   -6.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8756   -7.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1564   -6.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5885   -6.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3045   -7.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3045   -8.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0197   -8.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7336   -8.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7278   -7.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0120   -6.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1646   -8.5049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1659   -9.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8810   -9.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8823  -10.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5949   -9.3277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5974  -10.9777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5987  -11.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3139  -12.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3113  -10.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0264  -10.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
 16 11  1  0
  7  8  1  0
  4 17  1  0
 17 18  1  0
  7  9  2  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  1  0
 19 21  1  0
  2  3  1  0
 20 22  1  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  1  0
 11 12  2  0
 22 25  1  0
  6  1  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA93496

   1-{2-[3-(Diethylamino)-2-hydroxypropoxy]phenyl}-3-phenylpropan-1-one

2. Alternative Forms:

   

   ALA93496

   1-[2-[3-(Diethylamino)-2-hydroxypropoxy]phenyl]-3-phenylpropan-1-one;hydrochloride

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: 355.48

Molecular Weight (Monoisotopic): 355.2147

AlogP: 3.58

#Rotatable Bonds: 11

Polar Surface Area: 49.77

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.56

CX LogP: 3.75

CX LogD: 2.57

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.68

References

1. Chiba P, Burghofer S, Richter E, Tell B, Moser A, Ecker G..  (1995)  Synthesis, pharmacologic activity, and structure-activity relationships of a series of propafenone-related modulators of multidrug resistance.,  38  (14): [PMID:7629817] [10.1021/jm00014a031]

2. Ecker G, Chiba P, Hitzler M, Schmid D, Visser K, Cordes HP, Csöllei J, Seydel JK, Schaper KJ..  (1996)  Structure-activity relationship studies on benzofuran analogs of propafenone-type modulators of tumor cell multidrug resistance.,  39  (24): [PMID:8941391] [10.1021/jm960384x]

3. Fleischer R, Wiese M..  (2003)  Three-dimensional quantitative structure-activity relationship analysis of propafenone-type multidrug resistance modulators: influence of variable selection on test set predictivity.,  46  (23): [PMID:14584949] [10.1021/jm030876r]

4. Kaiser D, Terfloth L, Kopp S, Schulz J, de Laet R, Chiba P, Ecker GF, Gasteiger J..  (2007)  Self-organizing maps for identification of new inhibitors of P-glycoprotein.,  50  (7): [PMID:17352460] [10.1021/jm060604z]

5. Guiguemde WA, Shelat AA, Bouck D, Duffy S, Crowther GJ, Davis PH, Smithson DC, Connelly M, Clark J, Zhu F, Jiménez-Díaz MB, Martinez MS, Wilson EB, Tripathi AK, Gut J, Sharlow ER, Bathurst I, El Mazouni F, Fowble JW, Forquer I, McGinley PL, Castro S, Angulo-Barturen I, Ferrer S, Rosenthal PJ, Derisi JL, Sullivan DJ, Lazo JS, Roos DS, Riscoe MK, Phillips MA, Rathod PK, Van Voorhis WC, Avery VM, Guy RK..  (2010)  Chemical genetics of Plasmodium falciparum.,  465  (7296): [PMID:20485428] [10.1038/nature09099]

6. PubChem BioAssay data set, 

Source

Source(3):

• Scientific Literature
• St Jude Malaria Screening
• PubChem BioAssays