Phosphoric acid diethyl ester 4-nitro-phenyl ester

ID: ALA23838

Cas Number: 311-45-5

PubChem CID: 9395

Product Number: P114563, Order Now?

Max Phase: Unknown

Molecular Formula: C10H14NO6P

Molecular Weight: 275.20

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Diethyl p-nitrophenyl phosphate | Miotisal | Parathion oxygen analog | Phosphacol | E-600 | NSC-404110 | PARAOXON|311-45-5|Phosphacol|Diethyl paraoxon|Diethyl 4-nitrophenyl phosphate|Diethyl p-nitrophenyl phosphate|Miotisal|Ethyl paraoxon|Phosphachole|Mintacol|Paraoxon-ethyl|Chinorto|Fosfakol|Oxyparathion|Phosphakol|Phosphoric acid, diethyl 4-nitrophenyl ester|Chinorta|Mintaco|Paraoxone|Paroxan|Eticol|Miotisal A|Diethylparaoxon|Soluglacit|Soluglaucit|Ethyl paraoxan|p-Nitrophenyl diethyl phosphatShow More⌵

Canonical SMILES:  CCOP(=O)(OCC)Oc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

Standard InChI Key:  WYMSBXTXOHUIGT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    6.8042   -2.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5186   -2.3333    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -1.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9351   -3.0455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1015   -1.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0897   -2.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752   -2.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5266   -3.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9431   -4.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9482   -2.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9522   -3.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6704   -3.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3812   -3.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3694   -2.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6506   -1.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1022   -3.5309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8115   -3.1095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1125   -4.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  2  0
  3 10  1  0
  2  3  1  0
 10 11  2  0
  1  6  1  0
 11 12  1  0
  1  2  1  0
 12 13  2  0
  6  7  1  0
 13 14  1  0
  2  4  1  0
 14 15  2  0
 15 10  1  0
  4  8  1  0
  8  9  1  0
 16 17  2  0
 16 18  1  0
 13 16  1  0
M  CHG  2  16   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA23838

   PARAOXON

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 275.20

Molecular Weight (Monoisotopic): 275.0559

AlogP: 3.15

#Rotatable Bonds: 7

Polar Surface Area: 87.90

Molecular Species: ┄

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.43

Np Likeness Score: -0.57

References

1. Hill CM, Wu F, Cheng TC, DeFrank JJ, Raushel FM..  (2000)  Substrate and stereochemical specificity of the organophosphorus acid anhydrolase from Alteromonas sp. JD6.5 toward p-nitrophenyl phosphotriesters.,  10  (11): [PMID:10866401] [10.1016/s0960-894x(00)00213-4]

2. Bargota RS, Akhtar M, Biggadike K, Gani D, Allemann RK..  (2003)  Structure-activity relationship on human serum paraoxonase (PON1) using substrate analogues and inhibitors.,  13  (10): [PMID:12729627] [10.1016/s0960-894x(03)00290-7]

3. Cates LA, Li VS, Yakshe CC, Fadeyi MO, Andree TH, Karbon EW, Enna SJ..  (1984)  Phosphorus analogues of gamma-aminobutyric acid, a new class of anticonvulsants.,  27  (5): [PMID:6325692] [10.1021/jm00371a017]

4. Degorre F, Kiffer D, Terrier F..  (1988)  Sulfur derivatives of 2-oxopropanal oxime as reactivators of organophosphate-inhibited acetylcholinesterase in vitro: synthesis and structure-reactivity relationships.,  31  (4): [PMID:3351852] [10.1021/jm00399a012]

5. Nomura DK, Hudak CS, Ward AM, Burston JJ, Issa RS, Fisher KJ, Abood ME, Wiley JL, Lichtman AH, Casida JE..  (2008)  Monoacylglycerol lipase regulates 2-arachidonoylglycerol action and arachidonic acid levels.,  18  (22): [PMID:18752948] [10.1016/j.bmcl.2008.08.007]

6. Bharate SB, Guo L, Reeves TE, Cerasoli DM, Thompson CM..  (2010)  Bisquaternary pyridinium oximes: Comparison of in vitro reactivation potency of compounds bearing aliphatic linkers and heteroaromatic linkers for paraoxon-inhibited electric eel and recombinant human acetylcholinesterase.,  18  (2): [PMID:20005727] [10.1016/j.bmc.2009.11.052]

7. Guo L, Suarez AI, Braden MR, Gerdes JM, Thompson CM..  (2010)  Inhibition of acetylcholinesterase by chromophore-linked fluorophosphonates.,  20  (3): [PMID:20034789] [10.1016/j.bmcl.2009.12.007]

8. Nomura DK, Blankman JL, Simon GM, Fujioka K, Issa RS, Ward AM, Cravatt BF, Casida JE..  (2008)  Activation of the endocannabinoid system by organophosphorus nerve agents.,  4  (6): [PMID:18438404] [10.1038/nchembio.86]

9. Innocenti A, Supuran CT..  (2010)  Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of α- but not of β-, γ- and ζ-carbonic anhydrases.,  20  (21): [PMID:20833546] [10.1016/j.bmcl.2010.08.110]

10. PubChem BioAssay data set, 

11. Honda H, Tomizawa M, Casida JE..  (2007)  Insect muscarinic acetylcholine receptor: pharmacological and toxicological profiles of antagonists and agonists.,  55  (6): [PMID:17319687] [10.1021/jf0631934]

12. Finkelstein BL, Benner EA, Hendrixson MC, Kranis KT, Rauh JJ, Sethuraman MR, McCann SF..  (2002)  Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors.,  10  (3): [PMID:11814848] [10.1016/s0968-0896(01)00326-1]

13. Gao JR, Zhu KY..  (2000)  Comparative toxicity of selected organophosphate insecticides against resistant and susceptible clones of the greenbug, Schizaphis graminum (Homoptera: aphididae).,  48  (10): [PMID:11052723] [10.1021/jf000548p]

14. Kaleem Ahmed S, Belabassi Y, Sankaranarayanan L, Chao CK, Gerdes JM, Thompson CM..  (2013)  Synthesis and anti-acetylcholinesterase properties of novel β- and γ-substituted alkoxy organophosphonates.,  23  (7): [PMID:23453838] [10.1016/j.bmcl.2013.02.010]

15. PubChem BioAssay data set, 

16. PubChem BioAssay data set, 

17. WHO Anatomical Therapeutic Chemical Classification, 

18. Mohammed A, Sneathen J, Frojen SG, Kuo L, Dupureur CM..  (2017)  Stereospecific cholinesterase inhibition by O,S-diethylphenylphosphonothioate.,  25  (12): [PMID:28404526] [10.1016/j.bmc.2017.03.058]

19. Columbus I, Ghindes-Azaria L, Chen R, Yehezkel L, Redy-Keisar O, Fridkin G, Amir D, Marciano D, Drug E, Gershonov E, Klausner Z, Saphier S, Elias S, Pevzner A, Eichen Y, Parvari G, Smolkin B, Zafrani Y..  (2022)  Studying Lipophilicity Trends of Phosphorus Compounds by ³¹P-NMR Spectroscopy: A Powerful Tool for the Design of P-Containing Drugs.,  65  (12.0): [PMID:35678759] [10.1021/acs.jmedchem.2c00658]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• WHO Anatomical Therapeutic Chemical Classification