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

ID: ALA4085750

PubChem CID: 137642874

Max Phase: Preclinical

Molecular Formula: C11H15N2O7P

Molecular Weight: 318.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCP(=O)(O)[C@@H](O)c1cccc([N+](=O)[O-])c1)C(=O)O

Standard InChI:  InChI=1S/C11H15N2O7P/c12-9(10(14)15)4-5-21(19,20)11(16)7-2-1-3-8(6-7)13(17)18/h1-3,6,9,11,16H,4-5,12H2,(H,14,15)(H,19,20)/t9-,11+/m0/s1

Standard InChI Key:  CAYKXAFYYYAPJS-GXSJLCMTSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    7.3318   -6.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3307   -6.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0455   -7.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7619   -6.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7590   -6.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0436   -5.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6173   -5.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9029   -6.0794    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.1884   -5.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4740   -6.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7594   -5.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0451   -6.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592   -4.8424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3304   -5.6678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452   -6.9051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8957   -5.2541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8957   -6.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6171   -4.8418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4720   -5.6602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1879   -6.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4688   -4.8352    0.0000 O   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
  7 18  1  1
  5 19  1  0
 19 20  1  0
 19 21  2  0
M  CHG  2  19   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4085750

   ---

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: 318.22

Molecular Weight (Monoisotopic): 318.0617

AlogP: 0.66

#Rotatable Bonds: 7

Polar Surface Area: 163.99

Molecular Species: ZWITTERION

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.01

CX Basic pKa: 9.53

CX LogP: -2.09

CX LogD: -5.21

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.32

Np Likeness Score: -0.03

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