ethyl cyano-N,N-dimethylphosphonamidate

ID: ALA1097650

PubChem CID: 12443193

Max Phase: Preclinical

Molecular Formula: C5H11N2O2P

Molecular Weight: 162.13

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tabun | CHEMBL1097650

Canonical SMILES:  CCO[P@@](=O)(C#N)N(C)C

Standard InChI:  InChI=1S/C5H11N2O2P/c1-4-9-10(8,5-6)7(2)3/h4H2,1-3H3/t10-/m0/s1

Standard InChI Key:  PJVJTCIRVMBVIA-JTQLQIEISA-N

Molfile:  

     RDKit          2D

 10  9  0  0  0  0  0  0  0  0999 V2000
    8.4417   -5.5961    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.2645   -5.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6189   -5.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -4.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -3.9464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -6.4188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7278   -6.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1515   -6.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2034   -4.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6189   -4.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  4  5  3  0
  1  4  1  0
  1  6  1  1
  6  7  1  0
  6  8  1  0
  9 10  1  0
  3  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097650

   TABUN

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: 162.13

Molecular Weight (Monoisotopic): 162.0558

AlogP: 1.26

#Rotatable Bonds: 3

Polar Surface Area: 53.33

Molecular Species: ┄

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.12

CX LogD: -0.12

Aromatic Rings: ┄

Heavy Atoms: 10

QED Weighted: 0.59

Np Likeness Score: -0.49

References

1. Butini S, Campiani G, Borriello M, Gemma S, Panico A, Persico M, Catalanotti B, Ros S, Brindisi M, Agnusdei M, Fiorini I, Nacci V, Novellino E, Belinskaya T, Saxena A, Fattorusso C..  (2008)  Exploiting protein fluctuations at the active-site gorge of human cholinesterases: further optimization of the design strategy to develop extremely potent inhibitors.,  51  (11): [PMID:18479118] [10.1021/jm701253t]

2. Carletti E, Colletier JP, Dupeux F, Trovaslet M, Masson P, Nachon F..  (2010)  Structural evidence that human acetylcholinesterase inhibited by tabun ages through O-dealkylation.,  53  (10): [PMID:20408548] [10.1021/jm901853b]

Source

Source(1):

• Scientific Literature