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

ID: ALA4072316

PubChem CID: 137639752

Max Phase: Preclinical

Molecular Formula: C11H15N2O8P

Molecular Weight: 334.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCP(=O)(O)[C@H](O)c1ccc(O)c([N+](=O)[O-])c1)C(=O)O

Standard InChI:  InChI=1S/C11H15N2O8P/c12-7(10(15)16)3-4-22(20,21)11(17)6-1-2-9(14)8(5-6)13(18)19/h1-2,5,7,11,14,17H,3-4,12H2,(H,15,16)(H,20,21)/t7-,11-/m0/s1

Standard InChI Key:  GAGSUJFFXBSIDN-CPCISQLKSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    7.5860   -6.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5848   -7.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2997   -7.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0160   -7.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0132   -6.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2979   -6.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715   -6.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1570   -6.6378    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.4425   -6.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7281   -6.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135   -6.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992   -6.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0133   -5.4008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5846   -6.2261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2994   -7.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1499   -5.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1499   -7.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7262   -6.2186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4421   -6.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7230   -5.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7312   -7.8757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8713   -5.4001    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
  5 18  1  0
 18 19  1  0
 18 20  2  0
  4 21  1  0
  7 22  1  6
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4072316

   ---

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: 334.22

Molecular Weight (Monoisotopic): 334.0566

AlogP: 0.36

#Rotatable Bonds: 7

Polar Surface Area: 184.22

Molecular Species: ZWITTERION

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.97

CX Basic pKa: 9.53

CX LogP: -2.41

CX LogD: -6.26

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.27

Np Likeness Score: 0.38

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