(R,E)-(1-(4-(3-(trifluoromethyl)styryl)benzyl)pyrrolidin-2-yl)methanol hydrochloride

ID: ALA4782103

PubChem CID: 162663938

Max Phase: Preclinical

Molecular Formula: C21H23ClF3NO

Molecular Weight: 361.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.OC[C@H]1CCCN1Cc1ccc(/C=C/c2cccc(C(F)(F)F)c2)cc1

Standard InChI:  InChI=1S/C21H22F3NO.ClH/c22-21(23,24)19-4-1-3-17(13-19)9-6-16-7-10-18(11-8-16)14-25-12-2-5-20(25)15-26;/h1,3-4,6-11,13,20,26H,2,5,12,14-15H2;1H/b9-6+;/t20-;/m1./s1

Standard InChI Key:  PTEZUOBYIYVMAG-BXUUGTGLSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   36.2168  -10.1785    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.4718  -12.6413    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.8870  -11.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0644  -11.9265    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.1630  -11.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1618  -11.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8743  -12.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5925  -11.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5896  -11.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8725  -10.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3044  -10.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0221  -11.1121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1148  -11.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9240  -12.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3366  -11.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7799  -10.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5030  -12.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6830  -13.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4486  -12.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7377  -11.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0244  -12.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3134  -11.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6005  -12.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5976  -13.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3135  -13.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0234  -13.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8926  -11.1123    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 13 17  1  6
 17 18  1  0
  6 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 23  3  1  0
  3 27  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 361.41

Molecular Weight (Monoisotopic): 361.1653

AlogP: 4.83

#Rotatable Bonds: 5

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.14

CX LogP: 4.91

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -0.75

References

1. Li H,Sibley CD,Kharel Y,Huang T,Brown AM,Wonilowicz LG,Bevan DR,Lynch KR,Santos WL.  (2021)  Lipophilic tail modifications of 2-(hydroxymethyl)pyrrolidine scaffold reveal dual sphingosine kinase 1 and 2 inhibitors.,  30  [PMID:33385956] [10.1016/j.bmc.2020.115941]

Source

Source(1):

• Scientific Literature