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

ID: ALA1161819

PubChem CID: 46905552

Max Phase: Preclinical

Molecular Formula: C14H14F3NO7

Molecular Weight: 251.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](C[C@@]1(C(=O)O)Cc2ccccc2O1)C(=O)O.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C12H13NO5.C2HF3O2/c13-8(10(14)15)6-12(11(16)17)5-7-3-1-2-4-9(7)18-12;3-2(4,5)1(6)7/h1-4,8H,5-6,13H2,(H,14,15)(H,16,17);(H,6,7)/t8-,12+;/m0./s1

Standard InChI Key:  ZMAFBLUEOUDVPC-JIHQIIETSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    6.3708   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0853   -3.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7998   -4.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0853   -2.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -4.5833    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.7813   -4.8906    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9602   -3.4594    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9291    1.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3416    0.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0109    0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7523    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2993    2.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1051    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3609    1.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8122    0.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4583   -0.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875    1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2948    2.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2923    1.0219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8846   -0.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4861   -1.5703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7095   -0.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1358   -1.5383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1080   -0.1096    0.0000 O   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
 11 12  2  0
 18 19  1  0
  8 12  1  0
 18 20  2  0
 12 13  1  0
 17 21  1  0
 11  9  1  0
 21 22  1  1
 13 14  2  0
 21 23  1  0
  9 10  1  0
 23 24  1  0
 14 15  1  0
 23 25  2  0
 10  8  1  0
 15 16  2  0
 16 11  1  0
 10 17  1  1
 10 18  1  6
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: 251.24

Molecular Weight (Monoisotopic): 251.0794

AlogP: 0.25

#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: 1.72

CX Basic pKa: 9.25

CX LogP: -1.81

CX LogD: -5.06

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.71

Np Likeness Score: 0.85

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