(R)-(1-(4-(4-butylphenethyl)benzyl)pyrrolidin-2-yl)methanol hydrochloride

ID: ALA4782258

PubChem CID: 162663948

Max Phase: Preclinical

Molecular Formula: C24H34ClNO

Molecular Weight: 351.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCc1ccc(CCc2ccc(CN3CCC[C@@H]3CO)cc2)cc1.Cl

Standard InChI:  InChI=1S/C24H33NO.ClH/c1-2-3-5-20-7-9-21(10-8-20)11-12-22-13-15-23(16-14-22)18-25-17-4-6-24(25)19-26;/h7-10,13-16,24,26H,2-6,11-12,17-19H2,1H3;1H/t24-;/m1./s1

Standard InChI Key:  MTWAHKYYJQXOLW-GJFSDDNBSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   23.5324  -15.7535    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.2804  -16.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2792  -17.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9933  -17.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7131  -17.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7102  -16.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9915  -16.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4265  -16.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1459  -16.5768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2388  -17.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0497  -17.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4632  -16.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9053  -16.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6255  -17.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8060  -18.7676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5643  -17.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8518  -17.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1370  -17.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4244  -17.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7100  -17.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7071  -18.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4246  -19.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1361  -18.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9927  -19.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2797  -18.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5654  -19.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8524  -18.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
 10 14  1  6
 14 15  1  0
  3 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 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: 351.53

Molecular Weight (Monoisotopic): 351.2562

AlogP: 4.77

#Rotatable Bonds: 9

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: 9.22

CX LogP: 6.07

CX LogD: 4.25

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -0.28

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