(S)-1-carboxy-2-((S)-2-carboxy-7-methyl-2,3-dihydro-benzofuran-2-yl)-ethyl-ammonium trifluoroacetate

ID: ALA1161821

PubChem CID: 46905554

Max Phase: Preclinical

Molecular Formula: C15H16F3NO7

Molecular Weight: 265.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc2c1O[C@@](C[C@H](N)C(=O)O)(C(=O)O)C2.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C13H15NO5.C2HF3O2/c1-7-3-2-4-8-5-13(12(17)18,19-10(7)8)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:  COMPBAGTFXINEX-NAWISMDQSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
    9.9375  -10.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6520  -10.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3664  -10.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6520   -9.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2208  -11.3125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3480  -11.6198    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.5269  -10.1886    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0434   -8.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4566   -7.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7905   -7.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1269   -7.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8679   -8.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4157   -9.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2227   -9.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4789   -8.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9293   -7.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5719   -7.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1541   -6.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7731   -6.8204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2006   -8.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -9.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4617   -9.6426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8926   -9.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8770  -10.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6158   -9.2700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1850   -6.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
 17 19  1  0
 12 13  1  0
 10 20  1  1
  9 10  1  0
 20 21  1  0
 13 14  2  0
 21 22  1  1
 10  8  1  0
 21 23  1  0
 14 15  1  0
 23 24  1  0
  8 12  1  0
 23 25  2  0
 16 26  1  0
 15 16  2  0
 16 11  1  0
 10 17  1  6
 11 12  2  0
 17 18  2  0
 11  9  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: 1.84

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: 0.69

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