(4S)-3-[((4-Amino-4-carboxy)butyl)(hydroxy)phosphinyl]propanoic acid

ID: ALA1089175

PubChem CID: 46197881

Max Phase: Preclinical

Molecular Formula: C8H16NO6P

Molecular Weight: 253.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCCP(=O)(O)CCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C8H16NO6P/c9-6(8(12)13)2-1-4-16(14,15)5-3-7(10)11/h6H,1-5,9H2,(H,10,11)(H,12,13)(H,14,15)/t6-/m0/s1

Standard InChI Key:  NATYYJMHIDXUEG-LURJTMIESA-N

Molfile:  

     RDKit          2D

 16 15  0  0  0  0  0  0  0  0999 V2000
   13.7091   -3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4235   -3.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9946   -3.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2801   -3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5655   -3.1304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2801   -4.3680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9946   -2.3054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1380   -3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8526   -3.1304    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.8526   -2.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8450   -3.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5600   -3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2762   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9889   -3.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7051   -3.1397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9854   -4.3741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  4  5  1  0
  9 10  2  0
  1  3  1  0
  9 11  1  0
  4  6  2  0
  9 12  1  0
  1  2  1  0
 12 13  1  0
  3  7  1  1
 13 14  1  0
  3  4  1  0
 14 15  1  0
  2  8  1  0
 14 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1089175

   (2S)-2-amino-5-[2-carboxyethyl(hydroxy)phosphoryl]pentanoic 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: 253.19

Molecular Weight (Monoisotopic): 253.0715

AlogP: -0.08

#Rotatable Bonds: 8

Polar Surface Area: 137.92

Molecular Species: ZWITTERION

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.70

CX Basic pKa: 9.53

CX LogP: -3.23

CX LogD: -9.09

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.44

Np Likeness Score: 1.06

References

1. Selvam C, Oueslati N, Lemasson IA, Brabet I, Rigault D, Courtiol T, Cesarini S, Triballeau N, Bertrand HO, Goudet C, Pin JP, Acher FC..  (2010)  A virtual screening hit reveals new possibilities for developing group III metabotropic glutamate receptor agonists.,  53  (7): [PMID:20218620] [10.1021/jm901523t]

Source

Source(1):

• Scientific Literature