rac-amino(3-chlorophenyl)methylphosphonic acid

ID: ALA2252806

PubChem CID: 12069326

Max Phase: Preclinical

Molecular Formula: C7H9ClNO3P

Molecular Weight: 221.58

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C7H9ClNO3P/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:  FZNQUZMTQKQKPI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   21.7890  -16.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3809  -16.7240    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.2055  -16.7193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5262  -16.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5251  -17.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2396  -17.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9559  -17.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9529  -16.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2378  -16.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6657  -16.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6625  -15.4930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3845  -17.5521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8118  -16.3242    0.0000 Cl  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:

   

   ALA2252806

   AMINO(3-CHLOROPHENYL)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: 221.58

Molecular Weight (Monoisotopic): 221.0009

AlogP: 1.48

#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: 9.27

CX LogP: -0.48

CX LogD: -1.14

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.66

Np Likeness Score: -0.47

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