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

ID: ALA1788268

Cas Number: 107381-31-7

PubChem CID: 184819

Product Number: R342408, 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-/m1/s1

Standard InChI Key:  JWHAUXFOSRPERK-GOSISDBHSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    1.4609   -8.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714   -9.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -8.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714   -7.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933   -8.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1828  -10.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3198   -8.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -8.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933  -10.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980   -7.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933  -11.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0245   -7.6370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448   -9.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980   -6.8234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448   -7.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1828  -11.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151  -11.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7464   -8.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511   -7.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0344   -8.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1730   -8.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0344   -8.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151  -12.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1886  -12.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9047  -13.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  2  2  0
  6  2  1  0
  7 10  1  0
  8  4  1  0
  9  6  1  0
 10  8  1  0
 11  9  1  0
 12  7  1  0
 13  1  2  0
 10 14  1  6
 15  3  2  0
 16 11  2  0
 17 11  1  0
 18 12  1  0
 19 18  1  0
 20 13  1  0
 21 19  1  0
 22 20  2  0
 23 17  2  0
 24 16  1  0
 25 23  1  0
 15 22  1  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1788268

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

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

Source

Source(3):

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