[((3S)-3-Amino-3-carboxy)propyl][(4-hydroxy-3-nitrophenyl)methyl]phosphinic Acid

ID: ALA4082813

PubChem CID: 137646034

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)Cc1ccc(O)c([N+](=O)[O-])c1)C(=O)O

Standard InChI:  InChI=1S/C11H15N2O7P/c12-8(11(15)16)3-4-21(19,20)6-7-1-2-10(14)9(5-7)13(17)18/h1-2,5,8,14H,3-4,6,12H2,(H,15,16)(H,19,20)/t8-/m0/s1

Standard InChI Key:  ZJMMIQORYZRSFH-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    7.0809   -6.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0798   -6.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7878   -7.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4975   -6.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4946   -6.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7860   -5.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3731   -5.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -6.0797    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.9577   -5.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2501   -6.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5423   -5.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8347   -6.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5421   -4.8544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1268   -5.6720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349   -6.8976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6584   -5.2622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6584   -6.8966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2008   -5.6645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9100   -6.0704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1977   -4.8473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2058   -7.3059    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
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4082813

   ---

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: 0.87

#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: 1.32

CX Basic pKa: 9.53

CX LogP: -2.38

CX LogD: -5.97

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.33

Np Likeness Score: 0.15

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