(3S)-4-[((3-Amino-3-carboxy)propyl)(hydroxy)phosphinyl]-furanone

ID: ALA1092312

Max Phase: Preclinical

Molecular Formula: C8H14NO6P

Molecular Weight: 251.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCP(=O)(O)C1COC(=O)C1)C(=O)O

Standard InChI:  InChI=1S/C8H14NO6P/c9-6(8(11)12)1-2-16(13,14)5-3-7(10)15-4-5/h5-6H,1-4,9H2,(H,11,12)(H,13,14)/t5?,6-/m0/s1

Standard InChI Key:  GMZJHCHXTJKXKR-GDVGLLTNSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -3.4557  -23.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7412  -23.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0268  -23.4198    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118  -23.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0268  -24.2448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349  -22.5903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701  -23.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8846  -23.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5990  -23.0074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8846  -24.2448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701  -22.1824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5196  -23.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0478  -22.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458  -21.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3251  -22.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769  -22.5495    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
  4 12  1  0
  3  6  2  0
  1  2  1  0
  1  7  1  0
  3  4  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15  4  1  0
  7  8  1  0
 13 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092312

   ---

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: 251.17

Molecular Weight (Monoisotopic): 251.0559

AlogP: -0.63

#Rotatable Bonds: 5

Polar Surface Area: 126.92

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.59

CX Basic pKa: 9.53

CX LogP: -3.49

CX LogD: -6.66

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.44

Np Likeness Score: 1.51

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