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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:03:16 UTC

Update Date

2021-09-26 22:57:50 UTC

HMDB ID

HMDB0247901

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Acephate

Description

Acephate, also known as acetamidophos or acephic acid, belongs to the class of organic compounds known as organothiophosphorus compounds. These are organic derivatives of thiophosphonic acid, thiophosphoric acid, dithiophosphoric acid, or phosphorotrithioic acid, or derivatives thereof. Thiophosphonic acid, dithiophosphoric acid, thiophosphoric acid, and phosphorotrithioic acid are thiophosphorus compounds with the formula OP(O)(=S), OP(S)(=S)O, OP(O)(=S)O, and OP(=S)(S)S, respectively. Based on a literature review a significant number of articles have been published on Acephate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Acephate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Acephate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Acetamidophos	ChEBI
Acetylphosphoramidothioic acid O,S-dimethyl ester	ChEBI
N-(Methoxy(methylthio)phosphinoyl)acetamide	ChEBI
O,S-Dimethyl acetylamidothiophosphate	ChEBI
O,S-Dimethylacetylphosphoroamidothioate	ChEBI
Acetylphosphoramidothioate O,S-dimethyl ester	Generator
O,S-Dimethyl acetylamidothiophosphoric acid	Generator
O,S-Dimethylacetylphosphoroamidothioic acid	Generator
Acephic acid	Generator
Orthene	HMDB
O,S-Dimethyl N-acetyl phosphoramidothioate	HMDB

Chemical Formula

C₄H₁₀NO₃PS

Average Molecular Weight

183.166

Monoisotopic Molecular Weight

183.011900393

IUPAC Name

N-[methoxy(methylsulfanyl)phosphoryl]ethanimidic acid

Traditional Name

orthene

CAS Registry Number

Not Available

SMILES

COP(=O)(SC)N=C(C)O

InChI Identifier

InChI=1S/C4H10NO3PS/c1-4(6)5-9(7,8-2)10-3/h1-3H3,(H,5,6,7)

InChI Key

YASYVMFAVPKPKE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organothiophosphorus compounds. These are organic derivatives of thiophosphonic acid, thiophosphoric acid, dithiophosphoric acid, or phosphorotrithioic acid, or derivatives thereof. Thiophosphonic acid, dithiophosphoric acid, thiophosphoric acid, and phosphorotrithioic acid are thiophosphorus compounds with the formula OP(O)(=S), OP(S)(=S)O, OP(O)(=S)O, and OP(=S)(S)S, respectively.

Kingdom

Organic compounds

Super Class

Organophosphorus compounds

Class

Organothiophosphorus compounds

Sub Class

Not Available

Direct Parent

Organothiophosphorus compounds

Alternative Parents

Substituents

Sulfenyl compound
Organothiophosphorus compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic thiophosphate (CHEBI:34520 )
organothiophosphate insecticide (CHEBI:34520 )
mixed diacylamine (CHEBI:34520 )
phosphoramide (CHEBI:34520 )
Phosphoramido insecticides (C14426 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0247901)
Extracellular (HMDB: HMDB0247901)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Industrial application

Agrochemical (HMDB: HMDB0247901)

Agriculture

Pesticide

Acaricide (HMDB: HMDB0247901)

Biological role

Modulator

Inhibitor

EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0247901)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.46	ALOGPS
logP	0.038	ChemAxon
logS	-0.72	ALOGPS
pKa (Strongest Acidic)	7.61	ChemAxon
pKa (Strongest Basic)	0.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	41.57 m³·mol⁻¹	ChemAxon
Polarizability	16.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	132.606	30932474
DeepCCS	[M-H]-	129.844	30932474
DeepCCS	[M-2H]-	166.393	30932474
DeepCCS	[M+Na]+	141.673	30932474
AllCCS	[M+H]+	138.5	32859911
AllCCS	[M+H-H2O]+	134.8	32859911
AllCCS	[M+NH4]+	141.8	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	139.5	32859911
AllCCS	[M+HCOO]-	142.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acephate	COP(=O)(SC)N=C(C)O	2495.4	Standard polar	33892256
Acephate	COP(=O)(SC)N=C(C)O	1424.9	Standard non polar	33892256
Acephate	COP(=O)(SC)N=C(C)O	1432.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acephate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2020-08-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acephate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acephate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acephate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000g-9400000000-d893efedc95eeaf8effb	2014-10-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate LC-ESI-QTOF 10V, positive-QTOF	splash10-0006-0900000000-31a41e18b6879b3677e3	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate LC-ESI-QTOF 20V, positive-QTOF	splash10-0006-0900000000-6872feb4d8bb8fba6ae2	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate LC-ESI-QTOF 30V, positive-QTOF	splash10-006x-0900000000-9383d699f5d76d8695d7	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate LC-ESI-QTOF 40V, positive-QTOF	splash10-00dl-0900000000-eb6e1d653dc0e1c0c7a6	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate LC-ESI-QTOF 50V, positive-QTOF	splash10-00dl-0900000000-373ac93df09e3d99a747	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate NA , positive-QTOF	splash10-0006-0900000000-a0e0c32a7141fe16454c	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate NA , positive-QTOF	splash10-01ox-0900000000-7342f038060b24e1b3db	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate LC-ESI-QTOF 10V, negative-QTOF	splash10-001l-0900000000-1eae652f6550bcc1c3f9	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate NA , negative-QTOF	splash10-002f-2900000000-465a27f63f9ec638ae8a	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate 75V, Negative-QTOF	splash10-056r-9000000000-5d481d53939db5ab38d0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate 60V, Positive-QTOF	splash10-056r-9100000000-7516b07de3c668545f6e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate 90V, Negative-QTOF	splash10-004i-9000000000-a3d4c621409fbe04fe4f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate 60V, Negative-QTOF	splash10-056r-9100000000-11570f52ad761e8bb3dc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate 45V, Negative-QTOF	splash10-0a6u-9400000000-f7d9a542694720e5d5a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate 40V, Positive-QTOF	splash10-00dl-0900000000-7ada730c27884b185eac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate 75V, Positive-QTOF	splash10-01t9-9000000000-12bcc503c0ca532e898f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate 15V, Negative-QTOF	splash10-0006-3900000000-43fa8373838fd1cadd9e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate 50V, Positive-QTOF	splash10-00dl-0900000000-373ac93df09e3d99a747	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acephate 10V, Positive-QTOF	splash10-0006-0900000000-f5c73e90c92244ac1e98	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acephate 10V, Positive-QTOF	splash10-0002-8900000000-8fb8f18f81b00a48a9c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acephate 20V, Positive-QTOF	splash10-0002-9500000000-68f3aca4d8b0edadea8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acephate 40V, Positive-QTOF	splash10-0002-9400000000-2a66e01029c1323c88ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acephate 10V, Negative-QTOF	splash10-001j-1900000000-c74cd1ef6c4627e11bb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acephate 20V, Negative-QTOF	splash10-0002-9300000000-5607a2c51154cefeb2c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acephate 40V, Negative-QTOF	splash10-0002-9200000000-fc4140606bfa154b08fe	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1905

KEGG Compound ID

C14426

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acephate

METLIN ID

Not Available

PubChem Compound

1982

PDB ID

Not Available

ChEBI ID

34520

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Acephate (HMDB0247901)

MOL for HMDB0247901 (Acephate)

3D MOL for HMDB0247901 (Acephate)

3D SDF for HMDB0247901 (Acephate)

3D-SDF for HMDB0247901 (Acephate)

PDB for HMDB0247901 (Acephate)

3D PDB for HMDB0247901 (Acephate)

SMILES for HMDB0247901 (Acephate)

INCHI for HMDB0247901 (Acephate)

Structure for HMDB0247901 (Acephate)

3D Structure for HMDB0247901 (Acephate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra