2-[(1S,3S)-1-Hydroxy-3-((E)-3-hydroxy-7-phenyl-hept-1-enyl)-cyclohexyl]-N,N-dimethyl-acetamide

ID: ALA2112887

PubChem CID: 71452714

Max Phase: Preclinical

Molecular Formula: C23H35NO3

Molecular Weight: 373.54

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H35NO3/c1-24(2)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:  LQQOFRLZJKZLCO-DVUTXCTHSA-N

Molfile:  

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    1.9308   -4.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527   -3.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6484   -4.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -3.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5058   -3.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7953   -4.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3589   -3.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6370   -2.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3589   -2.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  1
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  6  5  2  0
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 20 13  1  0
 21 13  2  0
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 26 20  2  0
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 10 18  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA2112887

   2-[(1S,3S)-1-hydroxy-3-[(E,3S)-3-hydroxy-7-phenylhept-1-enyl]cyclohexyl]-N,N-dimethylacetamide

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: 373.54

Molecular Weight (Monoisotopic): 373.2617

AlogP: 3.72

#Rotatable Bonds: 9

Polar Surface Area: 60.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: 0.76

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