(3S)-3-[((3-Amino-3-carboxy)propyl)(hydroxy)phosphinyl]-3-trifluoromethypropanoic Acid

ID: ALA1093010

PubChem CID: 24780087

Max Phase: Preclinical

Molecular Formula: C8H13F3NO6P

Molecular Weight: 307.16

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C8H13F3NO6P/c9-8(10,11)5(3-6(13)14)19(17,18)2-1-4(12)7(15)16/h4-5H,1-3,12H2,(H,13,14)(H,15,16)(H,17,18)/t4-,5?/m0/s1

Standard InChI Key:  BKCHYPGHBXGCNX-ROLXFIACSA-N

Molfile:  

     RDKit          2D

 19 18  0  0  0  0  0  0  0  0999 V2000
    5.2572  -14.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9716  -14.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6861  -14.6989    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.4006  -14.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6861  -15.5239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6780  -13.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5426  -14.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282  -14.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1137  -14.2864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282  -15.5239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5426  -13.4614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1150  -14.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8296  -14.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5440  -14.6989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8296  -13.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4006  -13.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1150  -13.0489    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6861  -13.0489    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.3930  -12.6318    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
  8  9  1  0
 16 18  1  0
  3  5  1  0
 16 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093010

   (3S)-3-[((3-Amino-3-carboxy)propyl)(hydroxy)phosphinyl]-3-trifluoromethypropanoic 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: 307.16

Molecular Weight (Monoisotopic): 307.0433

AlogP: 0.46

#Rotatable Bonds: 7

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: 1.50

CX Basic pKa: 9.53

CX LogP: -2.50

CX LogD: -8.65

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.50

Np Likeness Score: 0.49

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