{(S)-1-[(7-Iodo-2,3-dioxo-1,2,3,4-tetrahydro-quinoxalin-5-ylmethyl)-amino]-ethyl}-phosphonic acid

ID: ALA354295

PubChem CID: 10048025

Max Phase: Preclinical

Molecular Formula: C11H13IN3O5P

Molecular Weight: 425.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](NCc1cc(I)cc2nc(O)c(O)nc12)P(=O)(O)O

Standard InChI:  InChI=1S/C11H13IN3O5P/c1-5(21(18,19)20)13-4-6-2-7(12)3-8-9(6)15-11(17)10(16)14-8/h2-3,5,13H,4H2,1H3,(H,14,16)(H,15,17)(H2,18,19,20)/t5-/m0/s1

Standard InChI Key:  OQCIHSFMLURANM-YFKPBYRVSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  1  0  0  0  0  0999 V2000
    8.9417   -2.6750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -1.4500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.9417   -4.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6542   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2250   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6542   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5125   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5125   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -1.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -0.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8000   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8000   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3750   -2.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3667   -4.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -2.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -1.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -4.3292    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  3  6  1  0
  4  1  2  0
  5  1  1  0
  6  5  2  0
  7  4  1  0
  8  5  1  0
  9 11  1  0
 10  6  1  0
 11 14  1  0
 12  2  2  0
 13  8  2  0
 14  8  1  0
 15 13  1  0
 16  4  1  0
 17  7  1  0
 18  2  1  0
 19  2  1  0
 20 15  1  0
  9 21  1  6
  7  3  2  0
 10 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA354295

   {(S)-1-[(7-Iodo-2,3-dioxo-1,2,3,4-tetrahydro-quinoxalin-5-ylmethyl)-amino]-ethyl}-phosphonic acid

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: 425.12

Molecular Weight (Monoisotopic): 424.9638

AlogP: 1.26

#Rotatable Bonds: 4

Polar Surface Area: 135.80

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -0.62

CX Basic pKa: 8.35

CX LogP: 0.12

CX LogD: -0.73

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.37

Np Likeness Score: -0.39

References

1. Ametamey SM, Kokic M, Carrey-Rémy N, Bläuenstein P, Willmann M, Bischoff S, Schmutz M, Schubiger PA, Auberson YP..  (2000)  Synthesis, radiolabelling and biological characterization of (D)-7-iodo-N-(1-phosphonoethyl)-5-aminomethylquinoxaline-2,3-dione, a glycine-binding site antagonist of NMDA receptors.,  10  (1): [PMID:10636248] [10.1016/s0960-894x(99)00576-4]

Source

Source(1):

• Scientific Literature