rac-amino(2,3-dimethoxyphenyl)methylphosphonic acid

ID: ALA2252825

PubChem CID: 24866950

Max Phase: Preclinical

Molecular Formula: C9H14NO5P

Molecular Weight: 247.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(C(N)P(=O)(O)O)c1OC

Standard InChI:  InChI=1S/C9H14NO5P/c1-14-7-5-3-4-6(8(7)15-2)9(10)16(11,12)13/h3-5,9H,10H2,1-2H3,(H2,11,12,13)

Standard InChI Key:  PZPWBGMCUWMVOI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   26.2108  -20.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8025  -20.8112    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.6273  -20.8064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9472  -20.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9459  -21.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6608  -22.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3771  -21.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3743  -20.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6590  -20.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0872  -20.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0841  -19.5799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8062  -21.6396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6564  -19.5860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9408  -19.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2326  -20.4113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5182  -20.8240    0.0000 C   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
 13 14  1  0
  4 15  1  0
 15 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252825

   AMINO(2,3-DIMETHOXYPHENYL)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: 247.19

Molecular Weight (Monoisotopic): 247.0610

AlogP: 0.84

#Rotatable Bonds: 4

Polar Surface Area: 102.01

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -0.33

CX Basic pKa: 8.86

CX LogP: -1.44

CX LogD: -2.12

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.68

Np Likeness Score: 0.17

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