(3R,5S)-7-(4-(4-fluorophenyl)-2-isopropylquinolin-3-yl)-3,5-dihydroxyhept-6-enoic acid

ID: ALA3951152

PubChem CID: 57494127

Max Phase: Preclinical

Molecular Formula: C25H26FNO4

Molecular Weight: 423.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1nc2ccccc2c(-c2ccc(F)cc2)c1/C=C/[C@@H](O)C[C@@H](O)CC(=O)O

Standard InChI:  InChI=1S/C25H26FNO4/c1-15(2)25-21(12-11-18(28)13-19(29)14-23(30)31)24(16-7-9-17(26)10-8-16)20-5-3-4-6-22(20)27-25/h3-12,15,18-19,28-29H,13-14H2,1-2H3,(H,30,31)/b12-11+/t18-,19-/m1/s1

Standard InChI Key:  HWEHUXJJTRFUKM-MCBHFWOFSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   16.6767   -6.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0933   -6.9438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0904   -6.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3818   -5.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3836   -7.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6756   -6.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9695   -7.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9702   -8.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6829   -8.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3861   -8.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9710   -5.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9721   -4.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2651   -4.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5566   -4.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5594   -5.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2669   -6.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3794   -4.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0859   -4.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0834   -3.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8394   -3.2519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3745   -3.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3721   -2.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6631   -2.0407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0786   -2.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7966   -5.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5059   -6.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7935   -4.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8482   -4.4912    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.0761   -1.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7826   -0.8086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3672   -0.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0
  5  2  2  0
  2  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  1 11  1  0
  4 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
  3 25  1  0
 25 26  1  0
 25 27  1  0
 14 28  1  0
 24 29  1  0
 29 30  1  0
 29 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3951152

   (E,3R,5S)-7-[4-(4-fluorophenyl)-2-propan-2-ylquinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid

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: 423.48

Molecular Weight (Monoisotopic): 423.1846

AlogP: 4.76

#Rotatable Bonds: 8

Polar Surface Area: 90.65

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.15

CX Basic pKa: 4.92

CX LogP: 3.33

CX LogD: 1.35

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: 0.18

References

1. Talele TT..  (2016)  The "Cyclopropyl Fragment" is a Versatile Player that Frequently Appears in Preclinical/Clinical Drug Molecules.,  59  (19): [PMID:27299736] [10.1021/acs.jmedchem.6b00472]

Source

Source(1):

• Scientific Literature