amino(phenyl)methylphosphonic acid

ID: ALA1090366

Cas Number: 18108-22-0

PubChem CID: 98449

Max Phase: Preclinical

Molecular Formula: C7H10NO3P

Molecular Weight: 187.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(c1ccccc1)P(=O)(O)O

Standard InChI:  InChI=1S/C7H10NO3P/c8-7(12(9,10)11)6-4-2-1-3-5-6/h1-5,7H,8H2,(H2,9,10,11)

Standard InChI Key:  ZKFNOUUKULVDOB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 12 12  0  0  0  0  0  0  0  0999 V2000
    4.7917   -4.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5061   -4.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2206   -4.4750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.5061   -3.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2206   -5.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9351   -4.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6372   -5.0584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2243   -2.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5093   -1.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924   -2.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7956   -2.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  7  2  0
  2  4  1  0
  4  8  2  0
  8  9  1  0
  3  5  1  0
  9 10  2  0
  2  3  1  0
 10 11  1  0
  3  6  1  0
 11 12  2  0
 12  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090366

   AMINO(PHENYL)METHYLPHOSPHONIC ACID

Molecule Features

Natural Product: Yes

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: 187.13

Molecular Weight (Monoisotopic): 187.0398

AlogP: 0.82

#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: 9.37

CX LogP: -1.05

CX LogD: -1.71

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.60

Np Likeness Score: 0.16

References

1. Grzywa R, Sokol AM, Sieńczyk M, Radziszewicz M, Kościołek B, Carty MP, Oleksyszyn J..  (2010)  New aromatic monoesters of alpha-aminoaralkylphosphonic acids as inhibitors of aminopeptidase N/CD13.,  18  (8): [PMID:20347318] [10.1016/j.bmc.2010.02.056]

2. Homan KT, Balasubramaniam D, Zabell AP, Wiest O, Helquist P, Stauffacher CV..  (2010)  Identification of novel inhibitors for a low molecular weight protein tyrosine phosphatase via virtual screening.,  18  (14): [PMID:20538467] [10.1016/j.bmc.2010.04.050]

3. 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]

4. 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]

5. Arya T, Reddi R, Kishor C, Ganji RJ, Bhukya S, Gumpena R, McGowan S, Drag M, Addlagatta A..  (2015)  Identification of the molecular basis of inhibitor selectivity between the human and streptococcal type I methionine aminopeptidases.,  58  (5): [PMID:25699713] [10.1021/jm501790e]

Source

Source(1):

• Scientific Literature