rac-amino(3-fluorophenyl)methylphosphonic acid

ID: ALA2252808

PubChem CID: 15255735

Max Phase: Preclinical

Molecular Formula: C7H9FNO3P

Molecular Weight: 205.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(c1cccc(F)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C7H9FNO3P/c8-6-3-1-2-5(4-6)7(9)13(10,11)12/h1-4,7H,9H2,(H2,10,11,12)

Standard InChI Key:  VRYPTNKNNGXIOV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   12.6426  -20.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2344  -21.0196    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.0590  -21.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3795  -21.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3784  -21.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0930  -22.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8093  -21.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8063  -21.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0911  -20.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5191  -20.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5160  -19.7886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2380  -21.8478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6651  -20.6198    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10  2  1  0
 10 11  1  0
  2 12  2  0
  4 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252808

   AMINO(3-FLUOROPHENYL)METHYLPHOSPHONIC 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: 205.12

Molecular Weight (Monoisotopic): 205.0304

AlogP: 0.96

#Rotatable Bonds: 2

Polar Surface Area: 83.55

Molecular Species: ZWITTERION

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -0.34

CX Basic pKa: 9.23

CX LogP: -0.90

CX LogD: -1.56

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.63

Np Likeness Score: -0.63

References

1. Forlani G, Occhipinti A, Berlicki L, Dziedzioła G, Wieczorek A, Kafarski P..  (2008)  Tailoring the structure of aminobisphosphonates to target plant P5C reductase.,  56  (9): [PMID:18399639] [10.1021/jf800029t]

2. Occhipinti A, Berlicki Ł, Giberti S, Dziedzioła G, Kafarski P, Forlani G..  (2010)  Effectiveness and mode of action of phosphonate inhibitors of plant glutamine synthetase.,  66  (1): [PMID:19697446] [10.1002/ps.1830]

Source

Source(1):

• Scientific Literature