Diethylphosphate
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Basic Info
| Common Name | Diethylphosphate(F05169) |
| 2D Structure | |
| Description | Diethylphosphate is product of metabolism and of environmental degradation of Chlorpyrifos (CPF; a commonly used diethylphosphorothionate organophosphorus (OP) insecticide) and are routinely measured in urine as biomarkers of exposure. (A3200). |
| FRCD ID | F05169 |
| CAS Number | 598-02-7 |
| PubChem CID | 654 |
| Formula | C4H11O4P |
| IUPAC Name | diethyl hydrogen phosphate |
| InChI Key | UCQFCFPECQILOL-UHFFFAOYSA-N |
| InChI | InChI=1S/C4H11O4P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3,(H,5,6) |
| Canonical SMILES | CCOP(=O)(O)OCC |
| Isomeric SMILES | CCOP(=O)(O)OCC |
| Synonyms |
phosphoric acid, diethyl ester
diethyl hydrogen phosphate
Diethyl phosphate
598-02-7
Diethyl acid phosphate
diethylphosphate
diethyl phosphoric acid
Diethylphosphoric acid
Ethyl phosphate, di-
O,O-Diethyl hydrogen phosphate
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic phosphoric acids and derivatives |
| Subclass | Phosphate esters |
| Intermediate Tree Nodes | Alkyl phosphates |
| Direct Parent | Dialkyl phosphates |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Dialkyl phosphate - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 154.102 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Complexity | 103 |
| Monoisotopic Mass | 154.039 |
| Exact Mass | 154.039 |
| XLogP | -0.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9072 |
| Human Intestinal Absorption | HIA+ | 0.8237 |
| Caco-2 Permeability | Caco2- | 0.5821 |
| P-glycoprotein Substrate | Non-substrate | 0.7950 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8864 |
| Non-inhibitor | 0.9384 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9344 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7790 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8629 |
| CYP450 2D6 Substrate | Non-substrate | 0.8446 |
| CYP450 3A4 Substrate | Non-substrate | 0.6540 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9360 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8896 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9246 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8669 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9496 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9520 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8439 |
| Non-inhibitor | 0.9184 | |
| AMES Toxicity | Non AMES toxic | 0.7811 |
| Carcinogens | Carcinogens | 0.7179 |
| Fish Toxicity | High FHMT | 0.5179 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7800 |
| Honey Bee Toxicity | High HBT | 0.8710 |
| Biodegradation | Not ready biodegradable | 0.8509 |
| Acute Oral Toxicity | III | 0.8425 |
| Carcinogenicity (Three-class) | Non-required | 0.5473 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.1442 | LogS |
| Caco-2 Permeability | 0.0386 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2499 | LD50, mol/kg |
| Fish Toxicity | 2.7033 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.7178 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Metabonomic analysis of the protective effect of quercetin on the toxicity induced by mixture of organophosphate pesticides in rat urine. | Hum Exp Toxicol | 2017 May | 27251765 |
| Efficiency of the intestinal bacteria in the degradation of the toxic pesticide, chlorpyrifos. | 3 Biotech | 2013 Apr | 28324568 |
| Urinary excretion of alkylphosphates in the general population (Italy). | Sci Total Environ | 1996 Jan 5 | 8584918 |
Targets
- General Function:
- Tetrahydrobiopterin binding
- Specific Function:
- Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH on 'Cys-247' implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM.
- Gene Name:
- NOS2
- Uniprot ID:
- P35228
- Molecular Weight:
- 131116.3 Da