(1S,3S)-1-Hydroxy-3-((E)-3-hydroxy-7-phenyl-hept-1-enyl)-cyclohexanecarboxylic acid

ID: ALA2112037

PubChem CID: 71454435

Max Phase: Preclinical

Molecular Formula: C20H27NaO4

Molecular Weight: 332.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([O-])[C@]1(O)CCC[C@H](/C=C/[C@@H](O)CCCCc2ccccc2)C1.[Na+]

Standard InChI:  InChI=1S/C20H28O4.Na/c21-18(11-5-4-9-16-7-2-1-3-8-16)13-12-17-10-6-14-20(24,15-17)19(22)23;/h1-3,7-8,12-13,17-18,21,24H,4-6,9-11,14-15H2,(H,22,23);/q;+1/p-1/b13-12+;/t17-,18+,20+;/m1./s1

Standard InChI Key:  AXAJAOFKFBECNI-MONIANJWSA-M

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   -1.4143   -1.4732    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    1.6214   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8995   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0480   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7698   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8995   -1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1891   -2.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4745   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0495   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4745   -4.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6214   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3391   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7656   -3.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0495   -2.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1964   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6230   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -2.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4761   -3.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4761   -2.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  1
  9  4  1  1
  5  4  2  0
  6  2  1  0
  7  3  2  0
  2  8  1  6
  9  6  1  0
 10  3  1  0
 11  2  1  0
 12  5  1  0
 13 17  1  0
 12 14  1  6
 15 11  1  0
 16 15  1  0
 17 21  1  0
 18 13  2  0
 19 13  1  0
 20 12  1  0
 21 22  1  0
 22 20  1  0
 23 19  2  0
 24 18  1  0
 25 23  1  0
 16  9  1  0
 24 25  2  0
M  CHG  2   1   1  10  -1
M  END

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: 332.44

Molecular Weight (Monoisotopic): 332.1988

AlogP: 3.32

#Rotatable Bonds: 8

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.01

CX Basic pKa: ┄

CX LogP: 3.93

CX LogD: 0.77

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: 1.32

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]

2. 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