[((3S)-3-Amino-3-carboxy)propyl][(4,5-dihydroxy-3-nitrophenyl)hydroxymethyl]phosphinic Acid

ID: ALA4094241

PubChem CID: 58058356

Max Phase: Preclinical

Molecular Formula: C11H15N2O9P

Molecular Weight: 350.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCP(=O)(O)C(O)c1cc(O)c(O)c([N+](=O)[O-])c1)C(=O)O

Standard InChI:  InChI=1S/C11H15N2O9P/c12-6(10(16)17)1-2-23(21,22)11(18)5-3-7(13(19)20)9(15)8(14)4-5/h3-4,6,11,14-15,18H,1-2,12H2,(H,16,17)(H,21,22)/t6-,11?/m0/s1

Standard InChI Key:  QOLNTYLPEHVBQY-OCAOPBLFSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    7.0850   -6.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0839   -7.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7919   -7.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5016   -7.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4988   -6.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7901   -6.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3772   -6.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696   -6.7236    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618   -6.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542   -6.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5464   -6.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -6.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462   -5.4983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1310   -6.3158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -7.5414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6626   -5.9061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6626   -7.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2049   -6.3084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9142   -6.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2019   -5.4912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2099   -7.9498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -8.7689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3770   -5.4976    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
  3 22  1  0
  7 23  1  0
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4094241

   (2S)-2-amino-4-[[(3,4-dihydroxy-5-nitrophenyl)-hydroxymethyl]-hydroxyphosphoryl]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: 350.22

Molecular Weight (Monoisotopic): 350.0515

AlogP: 0.07

#Rotatable Bonds: 7

Polar Surface Area: 204.45

Molecular Species: ZWITTERION

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.86

CX Basic pKa: 9.51

CX LogP: -2.79

CX LogD: -6.35

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.17

Np Likeness Score: 0.54

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