(3S)-3-[((3-Amino-3-carboxy)propyl)(hydroxy)phosphinyl]-2-(phosphonomethyl)propanoic Acid

ID: ALA1092593

PubChem CID: 46197779

Max Phase: Preclinical

Molecular Formula: C8H17NO9P2

Molecular Weight: 333.17

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C8H17NO9P2/c9-6(8(12)13)1-2-19(14,15)5(3-7(10)11)4-20(16,17)18/h5-6H,1-4,9H2,(H,10,11)(H,12,13)(H,14,15)(H2,16,17,18)/t5?,6-/m0/s1

Standard InChI Key:  OTYXWVKEWNCHHC-GDVGLLTNSA-N

Molfile:  

     RDKit          2D

 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.8372  -19.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1226  -19.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081  -19.5117    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6937  -19.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081  -20.3367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4163  -18.6820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5516  -19.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2661  -19.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9806  -19.0992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2661  -20.3367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5516  -18.2742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0208  -19.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353  -19.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4497  -19.5117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353  -18.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6937  -18.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081  -17.8616    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081  -17.0366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1226  -18.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1267  -17.4445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  8  9  1  0
 17 18  2  0
  3  5  1  0
 17 19  1  0
  8 10  2  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092593

   (2S)-2-amino-4-[(1-carboxy-3-phosphonopropan-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: 333.17

Molecular Weight (Monoisotopic): 333.0379

AlogP: -0.92

#Rotatable Bonds: 9

Polar Surface Area: 195.45

Molecular Species: ZWITTERION

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.50

CX Basic pKa: 9.53

CX LogP: -5.00

CX LogD: -13.29

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.29

Np Likeness Score: 0.80

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