[((3S)-3-Amino-3-carboxy)propyl][(4-morpholino-3-nitrophenyl)hydroxymethyl]phosphinic Acid

ID: ALA4082270

PubChem CID: 57765549

Max Phase: Preclinical

Molecular Formula: C15H22N3O8P

Molecular Weight: 403.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCP(=O)(O)C(O)c1ccc(N2CCOCC2)c([N+](=O)[O-])c1)C(=O)O

Standard InChI:  InChI=1S/C15H22N3O8P/c16-11(14(19)20)3-8-27(24,25)15(21)10-1-2-12(13(9-10)18(22)23)17-4-6-26-7-5-17/h1-2,9,11,15,21H,3-8,16H2,(H,19,20)(H,24,25)/t11-,15?/m0/s1

Standard InChI Key:  BWTDMGDNYYGBNJ-VPHXOMNUSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    7.1676   -6.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1664   -7.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8745   -7.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5841   -7.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5813   -6.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8727   -5.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4598   -5.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7522   -6.3397    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.0444   -5.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3367   -6.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289   -5.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -6.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6287   -5.1144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2135   -5.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9215   -7.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7451   -5.5222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7451   -7.1566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2875   -5.9245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9967   -6.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2844   -5.1073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2925   -7.5659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4596   -5.1138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2895   -8.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9938   -8.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7033   -8.3845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7040   -7.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9952   -7.1544    0.0000 C   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  0
 21 23  1  0
 21 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4082270

   (2S)-2-amino-4-[hydroxy-[hydroxy-(4-morpholin-4-yl-3-nitrophenyl)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: 403.33

Molecular Weight (Monoisotopic): 403.1145

AlogP: 0.49

#Rotatable Bonds: 8

Polar Surface Area: 176.46

Molecular Species: ZWITTERION

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.03

CX Basic pKa: 9.53

CX LogP: -2.19

CX LogD: -5.32

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.27

Np Likeness Score: -0.48

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