[((3S)-3-Amino-3-carboxy)propyl][(3-nitro-4-trifluoromethylphenyl)hydroxymethyl]phosphinic Acid

ID: ALA4063142

PubChem CID: 57765622

Max Phase: Preclinical

Molecular Formula: C12H14F3N2O7P

Molecular Weight: 386.22

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H14F3N2O7P/c13-12(14,15)7-2-1-6(5-9(7)17(21)22)11(20)25(23,24)4-3-8(16)10(18)19/h1-2,5,8,11,20H,3-4,16H2,(H,18,19)(H,23,24)/t8-,11?/m0/s1

Standard InChI Key:  RGHRXKZPSJWWED-YMNIQAILSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    7.0892   -6.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0880   -7.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7961   -7.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5057   -7.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5029   -6.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943   -6.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3814   -6.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6737   -6.4759    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.9659   -6.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2583   -6.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5505   -6.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429   -6.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503   -5.2506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351   -6.0682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8431   -7.2938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -5.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -7.2928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2091   -6.0607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9183   -6.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2060   -5.2435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2141   -7.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2154   -8.5193    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.9211   -7.2924    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.9177   -8.1100    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3812   -5.2500    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
 21 22  1  0
 21 23  1  0
 21 24  1  0
  7 25  1  0
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4063142

   (2S)-2-amino-4-[hydroxy-[hydroxy-[3-nitro-4-(trifluoromethyl)phenyl]methyl]phosphoryl]butanoic 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: 386.22

Molecular Weight (Monoisotopic): 386.0491

AlogP: 1.68

#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: 0.95

CX Basic pKa: 9.53

CX LogP: -1.24

CX LogD: -4.33

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.31

Np Likeness Score: -0.02

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