[((3S,1'R)-3-Amino-3-carboxy)propyl][(4-hydroxy-5-methoxy-3-nitrophenyl)hydroxymethyl]phosphinic Acid

ID: ALA4085558

PubChem CID: 124425164

Max Phase: Preclinical

Molecular Formula: C12H17N2O9P

Molecular Weight: 364.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@H](O)P(=O)(O)CC[C@H](N)C(=O)O)cc([N+](=O)[O-])c1O

Standard InChI:  InChI=1S/C12H17N2O9P/c1-23-9-5-6(4-8(10(9)15)14(19)20)12(18)24(21,22)3-2-7(13)11(16)17/h4-5,7,12,15,18H,2-3,13H2,1H3,(H,16,17)(H,21,22)/t7-,12+/m0/s1

Standard InChI Key:  PEXVMHLARUAHNC-JVXZTZIISA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    6.9901   -7.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9890   -8.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6970   -8.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4067   -8.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4038   -7.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6952   -6.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2823   -6.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5747   -7.3096    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.8669   -6.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593   -7.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4515   -6.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439   -7.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513   -6.0843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361   -6.9019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441   -8.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5676   -6.4921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5676   -8.1265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1100   -6.8944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8192   -7.3004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1069   -6.0772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2821   -6.0837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1150   -8.5358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6968   -9.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9890   -9.7634    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  1
  4 22  1  0
  3 23  1  0
 23 24  1  0
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4085558

   ---

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: 364.25

Molecular Weight (Monoisotopic): 364.0672

AlogP: 0.37

#Rotatable Bonds: 8

Polar Surface Area: 193.45

Molecular Species: ZWITTERION

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.86

CX Basic pKa: 9.53

CX LogP: -2.64

CX LogD: -5.97

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.24

Np Likeness Score: 0.34

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