rac-amino(2-chlorophenyl)methylphosphonic acid

ID: ALA2252822

PubChem CID: 12069325

Max Phase: Preclinical

Molecular Formula: C7H9ClNO3P

Molecular Weight: 221.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(c1ccccc1Cl)P(=O)(O)O

Standard InChI:  InChI=1S/C7H9ClNO3P/c8-6-4-2-1-3-5(6)7(9)13(10,11)12/h1-4,7H,9H2,(H2,10,11,12)

Standard InChI Key:  HPVJMDWKOFMDCY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
    9.7631  -16.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3550  -16.8938    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.1795  -16.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004  -16.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4992  -17.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2138  -18.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9299  -17.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9271  -16.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2120  -16.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6398  -16.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6366  -15.6629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3586  -17.7220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2095  -15.6690    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
  9 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252822

   AMINO(2-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: 9.13

CX LogP: -0.48

CX LogD: -1.15

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.66

Np Likeness Score: -0.40

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