(E)-3-(6-(2,6-dichlorostyryl)-2H-spiro[benzofuran-3,4'-piperidine]-1'-yl)propanoic acid hydrochloride

ID: ALA4218826

PubChem CID: 66655655

Max Phase: Preclinical

Molecular Formula: C23H24Cl3NO3

Molecular Weight: 432.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(O)CCN1CCC2(CC1)COc1cc(/C=C/c3c(Cl)cccc3Cl)ccc12

Standard InChI:  InChI=1S/C23H23Cl2NO3.ClH/c24-19-2-1-3-20(25)17(19)6-4-16-5-7-18-21(14-16)29-15-23(18)9-12-26(13-10-23)11-8-22(27)28;/h1-7,14H,8-13,15H2,(H,27,28);1H/b6-4+;

Standard InChI Key:  JBIYFAVZTBQJSB-CVDVRWGVSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   11.0876  -21.7991    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2414  -20.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0160  -20.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1854  -19.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5756  -19.0319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7888  -19.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6237  -20.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0286  -20.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0298  -21.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7547  -22.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7430  -20.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4595  -20.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630  -21.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2429  -21.9758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7256  -21.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7553  -18.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5390  -17.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7231  -17.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5109  -16.9179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1112  -16.6103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3079  -22.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2994  -22.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5864  -23.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8733  -22.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1525  -23.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1509  -24.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8686  -24.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5862  -24.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3094  -24.6340    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8727  -22.1419    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  9  2  0
  9 10  1  0
 10 13  2  0
 12 11  2  0
 11  8  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15  2  1  0
  2 12  1  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  9 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 28 29  1  0
 24 30  1  0
M  END

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: 432.35

Molecular Weight (Monoisotopic): 431.1055

AlogP: 5.36

#Rotatable Bonds: 5

Polar Surface Area: 49.77

Molecular Species: ZWITTERION

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.32

CX Basic pKa: 9.42

CX LogP: 2.37

CX LogD: 2.37

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: -0.07

References

1. Stoit AR, Lange JHM, Coolen HKAC, Rensink A, van den Hoogenband A, den Hartog AP, van Schaik S, Kruse CG..  (2018)  Spiro-1-benzofuranpiperidinylalkanoic acids as a novel and selective sphingosine S1P5 receptor agonist chemotype.,  28  (3): [PMID:29254642] [10.1016/j.bmcl.2017.12.018]

Source

Source(1):

• Scientific Literature