[((3S,1'S)-3-Amino-3-carboxy)propyl][(4-methoxy-3-nitrophenyl)hydroxymethyl]phosphinic Acid

ID: ALA4063720

PubChem CID: 137634883

Max Phase: Preclinical

Molecular Formula: C12H17N2O8P

Molecular Weight: 348.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc([C@@H](O)P(=O)(O)CC[C@H](N)C(=O)O)cc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C12H17N2O8P/c1-22-10-3-2-7(6-9(10)14(18)19)12(17)23(20,21)5-4-8(13)11(15)16/h2-3,6,8,12,17H,4-5,13H2,1H3,(H,15,16)(H,20,21)/t8-,12-/m0/s1

Standard InChI Key:  HSHWJQGGJKYMDI-UFBFGSQYSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    6.9282   -6.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9271   -7.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6351   -8.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3448   -7.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3419   -6.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6333   -6.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2204   -6.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5128   -6.7896    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.8050   -6.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -6.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3896   -6.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819   -6.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3894   -5.5643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9741   -6.3818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6821   -7.6075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5057   -5.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5057   -7.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0481   -6.3744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7573   -6.7803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0450   -5.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2202   -5.5636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0531   -8.0158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0544   -8.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  1
 12 14  1  0
 12 15  2  0
  8 16  2  0
  8 17  1  0
  5 18  1  0
 18 19  1  0
 18 20  2  0
  7 21  1  6
  4 22  1  0
 22 23  1  0
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4063720

   ---

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: 348.25

Molecular Weight (Monoisotopic): 348.0723

AlogP: 0.67

#Rotatable Bonds: 8

Polar Surface Area: 173.22

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.97

CX Basic pKa: 9.53

CX LogP: -2.27

CX LogD: -5.36

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.30

Np Likeness Score: 0.18

References

1. Selvam C, Lemasson IA, Brabet I, Oueslati N, Karaman B, Cabaye A, Tora AS, Commare B, Courtiol T, Cesarini S, McCort-Tranchepain I, Rigault D, Mony L, Bessiron T, McLean H, Leroux FR, Colobert F, Daniel H, Goupil-Lamy A, Bertrand HO, Goudet C, Pin JP, Acher FC..  (2018)  Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites.,  61  (5): [PMID:29397723] [10.1021/acs.jmedchem.7b01438]

Source

Source(1):

• Scientific Literature