rac-amino(2-bromophenyl)methylphosphonic acid

ID: ALA2252824

Cas Number: 174587-52-1

PubChem CID: 12038585

Max Phase: Preclinical

Molecular Formula: C7H9BrNO3P

Molecular Weight: 266.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(c1ccccc1Br)P(=O)(O)O

Standard InChI:  InChI=1S/C7H9BrNO3P/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:  WVJZCUVVKSVAMZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   17.8621  -19.2451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4539  -19.9616    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.2785  -19.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5990  -19.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5979  -20.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3124  -21.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0287  -20.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0259  -19.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3106  -19.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7386  -19.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7354  -18.7305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4575  -20.7898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3082  -18.7366    0.0000 Br  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:

   

   ALA2252824

   AMINO(2-BROMOPHENYL)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: 266.03

Molecular Weight (Monoisotopic): 264.9503

AlogP: 1.58

#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: 9.18

CX LogP: -0.28

CX LogD: -0.94

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.71

Np Likeness Score: -0.14

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