(1R)-1-{2-[(dimethylamino)oxy]-2-oxoethyl}-3-(3-hydroxy-7-phenyl-hept-1-enyl)cyclohexanol

ID: ALA153555

PubChem CID: 44366638

Max Phase: Preclinical

Molecular Formula: C23H35NO4

Molecular Weight: 389.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)OC(=O)C[C@@]1(O)CCC[C@H](/C=C/C(O)CCCCc2ccccc2)C1

Standard InChI:  InChI=1S/C23H35NO4/c1-24(2)28-22(26)18-23(27)16-8-12-20(17-23)14-15-21(25)13-7-6-11-19-9-4-3-5-10-19/h3-5,9-10,14-15,20-21,25,27H,6-8,11-13,16-18H2,1-2H3/b15-14+/t20-,21?,23-/m1/s1

Standard InChI Key:  LPYQKIWRXVPWPT-RRYBTIKCSA-N

Molfile:  

     RDKit          2D

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   -0.1583   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3083   -1.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -2.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4125   -0.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8875   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -1.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8875   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -3.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0458   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3667   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5250   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  6
 11  4  1  1
  5  4  2  0
  6  1  1  0
  7  1  2  0
  8  6  1  0
  9  3  1  0
  3 10  1  0
 11  9  1  0
 12  5  1  0
 13  3  1  0
 14 20  1  0
 15 12  1  0
 16 13  1  0
 17  8  1  0
 18  8  1  0
 19 16  1  0
 20 24  1  0
 21 14  1  0
 22 14  2  0
 23 12  1  0
 24 25  1  0
 25 23  1  0
 26 22  1  0
 27 21  2  0
 28 26  2  0
 19 11  1  0
 28 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA153555

   dimethylamino 2-[(1R,3S)-1-hydroxy-3-[(E)-3-hydroxy-7-phenylhept-1-enyl]cyclohexyl]acetate

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: 389.54

Molecular Weight (Monoisotopic): 389.2566

AlogP: 3.65

#Rotatable Bonds: 10

Polar Surface Area: 70.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.87

CX LogP: 3.65

CX LogD: 3.65

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: 1.03

References

1. Poudrel JM, Hullot P, Vidal JP, Girard JP, Rossi JC, Muller A, Bonne C, Bezuglov V, Serkov I, Renard P, Pfeiffer B..  (1999)  Synthesis and structure-activity relationships of new 1, 3-disubstituted cyclohexanes as structurally rigid leukotriene B(4) receptor antagonists.,  42  (26): [PMID:10639274] [10.1021/jm9910573]

Source

Source(1):

• Scientific Literature