(S)-1-carboxy-2-((S)-2-carboxy-5-methyl-2,3-dihydro-benzofuran-2-yl)-ethyl-ammonium trifluoroacetate

ID: ALA1161820

PubChem CID: 46905553

Max Phase: Preclinical

Molecular Formula: C15H16F3NO7

Molecular Weight: 265.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)C[C@](C[C@H](N)C(=O)O)(C(=O)O)O2.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C13H15NO5.C2HF3O2/c1-7-2-3-10-8(4-7)5-13(19-10,12(17)18)6-9(14)11(15)16;3-2(4,5)1(6)7/h2-4,9H,5-6,14H2,1H3,(H,15,16)(H,17,18);(H,6,7)/t9-,13-;/m0./s1

Standard InChI Key:  WRBYOSJUFDCWEB-NAWISMDQSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
   -2.7274   -8.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3142   -7.6861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9803   -8.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -8.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9029   -8.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551   -9.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5481   -9.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919   -8.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8415   -8.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989   -7.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6167   -6.7827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9977   -7.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702   -8.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5859   -9.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3091   -9.9801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782  -10.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938  -10.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1550   -9.6075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0024  -10.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833  -12.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311  -11.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1456  -12.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311  -10.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000  -12.5583    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271  -12.8656    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6939  -11.4344    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  9  4  1  0
  3 10  1  6
  4  5  2  0
 10 11  2  0
  4  2  1  0
 10 12  1  0
  5  6  1  0
  3 13  1  1
  2  3  1  0
 13 14  1  0
  6  7  2  0
 14 15  1  1
  3  1  1  0
 14 16  1  0
  7  8  1  0
 16 17  1  0
  1  5  1  0
 16 18  2  0
  7 19  1  0
 20 24  1  0
 20 25  1  0
 21 22  1  0
 20 26  1  0
 21 23  2  0
 20 21  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: 265.26

Molecular Weight (Monoisotopic): 265.0950

AlogP: 0.56

#Rotatable Bonds: 4

Polar Surface Area: 109.85

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.82

CX Basic pKa: 9.25

CX LogP: -1.28

CX LogD: -4.51

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.73

Np Likeness Score: 0.76

References

1. Cohen JL, Limon A, Miledi R, Chamberlin AR..  (2006)  Design, synthesis, and biological evaluation of a scaffold for iGluR ligands based on the structure of (-)-dysiherbaine.,  16  (8): [PMID:16455241] [10.1016/j.bmcl.2006.01.047]

Source

Source(1):

• Scientific Literature