1-(2-((4'-chloro-2'-fluorobiphenyl-2-yl)methyleneaminooxy)ethyl)pyrrolidine-3-carboxylic acid

ID: ALA4476777

PubChem CID: 155538624

Max Phase: Preclinical

Molecular Formula: C20H20ClFN2O3

Molecular Weight: 390.84

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)C1CCN(CCO/N=C/c2ccccc2-c2ccc(Cl)cc2F)C1

Standard InChI:  InChI=1S/C20H20ClFN2O3/c21-16-5-6-18(19(22)11-16)17-4-2-1-3-14(17)12-23-27-10-9-24-8-7-15(13-24)20(25)26/h1-6,11-12,15H,7-10,13H2,(H,25,26)/b23-12+

Standard InChI Key:  AEMYERASLKNPIX-FSJBWODESA-N

Molfile:  

 
     RDKit          2D

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    3.3905  -13.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2077  -13.1689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9819  -12.4612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9819  -13.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954  -18.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942  -19.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4023  -20.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1119  -19.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1091  -18.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005  -18.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862  -20.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2804  -19.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5729  -20.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5718  -20.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841  -21.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9888  -20.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876  -18.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9874  -17.5821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2796  -17.1737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794  -16.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5716  -15.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5714  -15.1309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346  -14.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646  -13.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9124  -14.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978  -21.2558    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.8643  -21.2591    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  2  0
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  5 17  1  0
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  4 24  1  0
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 16 26  1  0
 14 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476777

   ---

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: 390.84

Molecular Weight (Monoisotopic): 390.1146

AlogP: 3.90

#Rotatable Bonds: 7

Polar Surface Area: 62.13

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.23

CX Basic pKa: 8.37

CX LogP: 1.54

CX LogD: 1.51

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: -1.28

References

1. Huber SK, Höfner G, Wanner KT..  (2019)  Application of the concept of oxime library screening by mass spectrometry (MS) binding assays to pyrrolidine-3-carboxylic acid derivatives as potential inhibitors of γ-aminobutyric acid transporter 1 (GAT1).,  27  (13): [PMID:31097402] [10.1016/j.bmc.2019.05.001]

Source

Source(1):

• Scientific Literature