(3S)-3-[((3-Amino-3-carboxylate)propyl)(hydroxy)phosphinate]-3-hydroxymethylpropanoate

ID: ALA1092313

PubChem CID: 46197782

Max Phase: Preclinical

Molecular Formula: C8H16NO7P

Molecular Weight: 269.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCP(=O)(O)C(CO)CC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C8H16NO7P/c9-6(8(13)14)1-2-17(15,16)5(4-10)3-7(11)12/h5-6,10H,1-4,9H2,(H,11,12)(H,13,14)(H,15,16)/t5?,6-/m0/s1

Standard InChI Key:  CLUHLHVRNKPCNZ-GDVGLLTNSA-N

Molfile:  

     RDKit          2D

 17 16  0  0  0  0  0  0  0  0999 V2000
    5.1289  -23.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8433  -22.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5578  -23.2518    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.2724  -22.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5578  -24.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5498  -22.4221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4144  -22.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6999  -23.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854  -22.8393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6999  -24.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4144  -22.0142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9868  -23.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7013  -22.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4158  -23.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7013  -22.0142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2724  -22.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9868  -21.6017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  3  5  1  0
  8 10  2  0
  2  3  1  0
  7 11  1  1
  3  6  2  0
  4 12  1  0
  1  2  1  0
 12 13  1  0
  1  7  1  0
 13 14  1  0
  3  4  1  0
 13 15  2  0
  7  8  1  0
  4 16  1  0
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092313

   (2S)-2-amino-4-[(1-carboxy-3-hydroxypropan-2-yl)-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: 269.19

Molecular Weight (Monoisotopic): 269.0664

AlogP: -1.11

#Rotatable Bonds: 8

Polar Surface Area: 158.15

Molecular Species: ZWITTERION

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.59

CX Basic pKa: 9.53

CX LogP: -4.16

CX LogD: -10.17

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.35

Np Likeness Score: 0.99

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