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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:43:49 UTC

Update Date

2022-03-07 02:53:55 UTC

HMDB ID

HMDB0033956

Secondary Accession Numbers

HMDB33956

Metabolite Identification

Common Name

Dichlorvos

Description

Dichlorvos is used as a household and public health fumigant, for crop protection and as an anthelmintic in animal feeds.Dichlorvos or 2,2-dichlorovinyl dimethyl phosphate (DDVP) is a highly volatile organophosphate, widely used as a insecticide to control household pests, in public health, and protecting stored product from insects. It is effective against mushroom flies, aphids, spider mites, caterpillars, thrips, and whiteflies in greenhouse, outdoor fruit, and vegetable crops. (Wikipedia

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,2-Dichloroethenyl dimethyl phosphate	ChEBI
DDVP	ChEBI
Dimethyl 2,2-dichlorovinyl phosphate	ChEBI
Dimethyl-2,2-dichlorovinyl phosphate	ChEBI
Phosphoric acid, 2,2-dichloroethenyl dimethyl ester	ChEBI
Phosphoric acid, 2,2-dichlorovinyl dimethyl ester	ChEBI
Atgard	Kegg
2,2-Dichloroethenyl dimethyl phosphoric acid	Generator
Dimethyl 2,2-dichlorovinyl phosphoric acid	Generator
Dimethyl-2,2-dichlorovinyl phosphoric acid	Generator
Phosphate, 2,2-dichloroethenyl dimethyl ester	Generator
Phosphate, 2,2-dichlorovinyl dimethyl ester	Generator
Dichlofos	MeSH
Dichlorophos	MeSH
Dimethyl dichlorovinyl phosphate	MeSH
Divipan	MeSH
Novotox	MeSH
Phosphoric acid 2,2 dichloroethenyl dimethyl ester	MeSH
Phosphoric acid 2,2-dichloroethenyl dimethyl ester	MeSH
2,2-Dichloroethenol dimethyl phosphate	HMDB
2,2-Dichloroethenyl phosphoric acid dimethyl ester	HMDB
2,2-Dichlorovinyl alcohol dimethyl phosphate	HMDB
2,2-Dichlorovinyl dimethyl phosphate, 8ci	HMDB
2,2-Dichlorovinyl dimethyl phosphoric acid ester	HMDB
2,2-Dichlorovinyl-O,O-dimethyl phosphate	HMDB
2,2-Dimethyldichlorovinyl phosphate	HMDB
Algard	HMDB
Apavap	HMDB
Aquaguard	HMDB
Astrobot	HMDB
Benfos	HMDB
Bibesol	HMDB
Brevinyl	HMDB
Canogard	HMDB
Cekusan	HMDB
Chlorvinphos	HMDB
Cyanophos	HMDB
Cypona	HMDB
DDVP (Insecticide)	HMDB
Dichloroethenyl dimethyl phosphate	HMDB
Diclorvos	HMDB
Dimethyl 2,2-dichloroethenyl phosphate	HMDB
Dimethyl O,O-dichlorovinyl-2,2-phosphate	HMDB
Dimethyldichlorovinyl phosphate	HMDB
Duravos	HMDB
Equigand	HMDB
Equigard	HMDB
Equigel	HMDB
Equiguard	HMDB
Ethenol, 2,2-dichloro-, dimethyl phosphate	HMDB
Fecama	HMDB
Herkal	HMDB
Herkol	HMDB
Insectigas D	HMDB
Krecalvin	HMDB
Lindan	HMDB
Lindanmafu	HMDB
Nerkol	HMDB
Nogos	HMDB
NSC 6738	HMDB
Nuvan	HMDB
O,O-Dimethyl 2,2-dichlorovinyl phosphate	HMDB
O,O-Dimethyl dichlorovinyl phosphate	HMDB
O-(2,2-Dichloroethenyl) O,O-dimethyl phosphate, 9ci	HMDB
O-(2,2-Dichlorvinyl)-O,O-dimethylphosphate	HMDB
Panaplate	HMDB
Phosphoric acid 2,2-dichlorovinyl dimethyl ester	HMDB
Phosvit	HMDB
Tetravos	HMDB
Topanol	HMDB
Unifos	HMDB
Unitox	HMDB
Vapona	HMDB
Verdican	HMDB
Verdipor	HMDB
Verdisol	HMDB

Chemical Formula

C₄H₇Cl₂O₄P

Average Molecular Weight

220.976

Monoisotopic Molecular Weight

219.945900638

IUPAC Name

2,2-dichloroethenyl dimethyl phosphate

Traditional Name

dichlorvos

CAS Registry Number

62-73-7

SMILES

COP(=O)(OC)OC=C(Cl)Cl

InChI Identifier

InChI=1S/C4H7Cl2O4P/c1-8-11(7,9-2)10-3-4(5)6/h3H,1-2H3

InChI Key

OEBRKCOSUFCWJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Dialkyl phosphates

Alternative Parents

Substituents

Dialkyl phosphate
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organochlorine acaricide (CHEBI:34690 )
dialkyl phosphate (CHEBI:34690 )
organophosphate insecticide (CHEBI:34690 )
alkenyl phosphate (CHEBI:34690 )
Organophosphorus insecticides (C14430 )
a small molecule (CPD-10185 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0033956)
Hypotension (HMDB: HMDB0033956)

Nervous system disorder

Headache (HMDB: HMDB0033956)
Tremor (HMDB: HMDB0033956)

Central nervous system disorder

Psychiatric disorder

Depression (HMDB: HMDB0033956)
Anxiety (HMDB: HMDB0033956)

Digestive system disorder

Gastrointestinal disorder

Vomiting (HMDB: HMDB0033956)
Nausea (HMDB: HMDB0033956)

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033956)
Cytoplasm (HMDB: HMDB0033956)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0033956)
Inhalation (HMDB: HMDB0033956)

Enteral

Ingestion (HMDB: HMDB0033956)

Source

Exogenous

Food

Food (HMDB: HMDB0033956)

Synthetic

Synthetic (HMDB: HMDB0033956)

Process

Not Available

Role

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-60 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	8 mg/mL at 20 °C	Not Available
LogP	1.43	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	138.69	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001270

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.77 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.37	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	-9.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.19 m³·mol⁻¹	ChemAxon
Polarizability	16.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	137.902	30932474
DeepCCS	[M-H]-	135.014	30932474
DeepCCS	[M-2H]-	171.437	30932474
DeepCCS	[M+Na]+	146.975	30932474
AllCCS	[M+H]+	144.6	32859911
AllCCS	[M+H-H2O]+	141.1	32859911
AllCCS	[M+NH4]+	147.8	32859911
AllCCS	[M+Na]+	148.8	32859911
AllCCS	[M-H]-	139.6	32859911
AllCCS	[M+Na-2H]-	141.7	32859911
AllCCS	[M+HCOO]-	144.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dichlorvos	COP(=O)(OC)OC=C(Cl)Cl	1932.0	Standard polar	33892256
Dichlorvos	COP(=O)(OC)OC=C(Cl)Cl	1324.7	Standard non polar	33892256
Dichlorvos	COP(=O)(OC)OC=C(Cl)Cl	1251.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dichlorvos EI-B (Non-derivatized)	splash10-0a4i-1900000000-09877a8cb478a3cc6839	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dichlorvos EI-B (Non-derivatized)	splash10-0a4i-1900000000-09877a8cb478a3cc6839	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dichlorvos GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-7950000000-d8cdc825bf993c643600	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dichlorvos GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dichlorvos GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-7900000000-0efae19e253ed849b729	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , negative-QTOF	splash10-001i-0900000000-f98de9faf1be0bb7aa83	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , negative-QTOF	splash10-001i-0900000000-93c62701332435cee993	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , negative-QTOF	splash10-001i-0900000000-f922e6ba3c6c6b90775a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , negative-QTOF	splash10-001i-1900000000-40a51b0033ce31d71432	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , negative-QTOF	splash10-001i-1900000000-9ef61f0d99a23257c13d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , negative-QTOF	splash10-001i-3900000000-c65f2474371722a3bcc8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos 45V, Negative-QTOF	splash10-001i-0900000000-f922e6ba3c6c6b90775a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos 30V, Negative-QTOF	splash10-001i-0900000000-93c62701332435cee993	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos 60V, Negative-QTOF	splash10-001i-1900000000-40a51b0033ce31d71432	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos 75V, Negative-QTOF	splash10-001i-1900000000-9ef61f0d99a23257c13d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos 15V, Negative-QTOF	splash10-001i-0900000000-f98de9faf1be0bb7aa83	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos 90V, Negative-QTOF	splash10-001i-3900000000-c65f2474371722a3bcc8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , positive-QTOF	splash10-00fr-0690000000-26446ccc45ba04ecd6a2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , positive-QTOF	splash10-004i-0930000000-5337a3d357153a9b46f2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , positive-QTOF	splash10-004i-0900000000-65501644b18b2b26ba71	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , positive-QTOF	splash10-004i-2900000000-051c8cc88647cdf4959e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , positive-QTOF	splash10-004i-4900000000-dccb667225335d52f6d1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , positive-QTOF	splash10-004i-6900000000-8c14f2901d28ffb6e55a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-cc2455ee44a59b12a9f4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-ITFT , positive-QTOF	splash10-004i-2900000000-c792ae223d6916b397d8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-ITFT , positive-QTOF	splash10-0a4l-0900000000-ca0ee2a0d7d29061a4c4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-ITFT , positive-QTOF	splash10-052f-0900000000-347f95538a81149f9317	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos LC-ESI-QFT , positive-QTOF	splash10-004i-0930000000-62f725b3cb5b2d33fd64	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos 45V, Positive-QTOF	splash10-004i-0900000000-a16d9953cbbf3ee35661	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dichlorvos 30V, Positive-QTOF	splash10-004i-0930000000-2ea542aeab9013b4a45e	2021-09-20	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11397

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012175

KNApSAcK ID

Not Available

Chemspider ID

2931

KEGG Compound ID

C14430

BioCyc ID

CPD-10185

BiGG ID

Not Available

Wikipedia Link

Dichlorvos

METLIN ID

Not Available

PubChem Compound

3039

PDB ID

Not Available

ChEBI ID

34690

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Choudhary S, Raheja G, Gupta V, Gill KD: Possible involvement of dopaminergic neurotransmitter system in dichlorvos induced delayed neurotoxicity. J Biochem Mol Biol Biophys. 2002 Feb;6(1):29-36. [PubMed:12186780 ]
Ebeigbe AB, Campbell PI: Inhibitory effect of dichlorvos on arterial smooth muscle contraction. Pharmacol Res Commun. 1986 Mar;18(3):283-91. [PubMed:3725847 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Dichlorvos (HMDB0033956)

MOL for HMDB0033956 (Dichlorvos)

3D MOL for HMDB0033956 (Dichlorvos)

3D SDF for HMDB0033956 (Dichlorvos)

3D-SDF for HMDB0033956 (Dichlorvos)

PDB for HMDB0033956 (Dichlorvos)

3D PDB for HMDB0033956 (Dichlorvos)

SMILES for HMDB0033956 (Dichlorvos)

INCHI for HMDB0033956 (Dichlorvos)

Structure for HMDB0033956 (Dichlorvos)

3D Structure for HMDB0033956 (Dichlorvos)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra