[(3S*R*,Z)-3-((3S*R*,E)-3-Hydroxy-7-phenyl-1-hepten-1-yl)cyclohexylidene]-N,N-dimethyl-acetamide

ID: ALA264039

PubChem CID: 44366652

Max Phase: Preclinical

Molecular Formula: C23H33NO3

Molecular Weight: 371.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H33NO3/c1-24(2)27-23(26)18-21-13-8-12-20(17-21)15-16-22(25)14-7-6-11-19-9-4-3-5-10-19/h3-5,9-10,15-16,18,20,22,25H,6-8,11-14,17H2,1-2H3/b16-15+,21-18-/t20-,22?/m1/s1

Standard InChI Key:  GROGAXYRPIVKQC-GJFTZNTESA-N

Molfile:  

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    3.5875   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1875   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3042   -2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7792   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3042   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 19  1  0
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 20 13  1  0
 21 13  2  0
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 27 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA264039

   dimethylamino (2Z)-2-[(3S)-3-[(E)-3-hydroxy-7-phenylhept-1-enyl]cyclohexylidene]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: 371.52

Molecular Weight (Monoisotopic): 371.2460

AlogP: 4.45

#Rotatable Bonds: 9

Polar Surface Area: 49.77

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.22

CX LogP: 5.00

CX LogD: 5.00

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.30

Np Likeness Score: 0.75

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