1-[2-(4-Amino-2-hydroxy-heptyloxy)-phenyl]-3-phenyl-propan-1-one

ID: ALA1322675

Cas Number: 107381-32-8

PubChem CID: 184820

Product Number: P342409, Order Now?

Max Phase: Preclinical

Molecular Formula: C21H27NO3

Molecular Weight: 341.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC[C@H](O)COc1ccccc1C(=O)CCc1ccccc1

Standard InChI:  InChI=1S/C21H27NO3/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17/h3-11,18,22-23H,2,12-16H2,1H3/t18-/m0/s1

Standard InChI Key:  JWHAUXFOSRPERK-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    7.7185   -1.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7173   -2.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4339   -2.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1521   -2.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1493   -1.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4321   -0.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8627   -0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5728   -1.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2872   -0.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0015   -1.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0013   -2.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7148   -2.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4274   -2.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4221   -1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7081   -0.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2854   -0.0498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7028   -0.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4164    0.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1353   -0.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8489    0.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1406   -0.8631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5636   -0.0276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2771    0.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9960   -0.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7096    0.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
  6  1  1  0
 13 14  1  0
  2  3  1  0
 14 15  2  0
 15 10  1  0
  5  7  1  0
  9 16  2  0
 15 17  1  0
  7  8  1  0
 17 18  1  0
  3  4  2  0
 18 19  1  0
  8  9  1  0
 19 20  1  0
  1  2  2  0
 19 21  1  6
  9 10  1  0
 20 22  1  0
  4  5  1  0
 22 23  1  0
 10 11  2  0
 23 24  1  0
 24 25  1  0
 11 12  1  0
  5  6  2  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA1322675

   (S)-(-)-propafenone hydrochloride

2. Parent:

   

   ALA1322675

   (S)-Propafenone

Molecule Features

Natural Product: Yes

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: 341.45

Molecular Weight (Monoisotopic): 341.1991

AlogP: 3.24

#Rotatable Bonds: 11

Polar Surface Area: 58.56

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.63

CX LogP: 3.54

CX LogD: 1.34

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.49

Np Likeness Score: -0.36

References

1. Chiba P, Rebitzer S, Richter E, Hitzler M, Ecker G..  (1998)  Synthesis and pharmacological activity of the stereoisomers of GP-88, a propafenone-type modulator of multidrug resistance.,  8  (7): [PMID:9871549] [10.1016/s0960-894x(98)00115-2]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. Ecker GF and Chiba P. Structure-activity data for a series of P-glycoprotein inhibitors (Supplementary Data to CHEMBL1142990),  [10.6019/CHEMBL2449286]

8. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• Deposited Supplementary Bioactivity Data
• AstraZeneca Deposited Data