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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:34 UTC

Update Date

2023-02-21 17:21:19 UTC

HMDB ID

HMDB0031803

Secondary Accession Numbers

HMDB31803

Metabolite Identification

Common Name

(±)-Methamidophos

Description

(±)-Methamidophos, also known as metamidophos or monitor, belongs to the class of organic compounds known as phosphoramidothioic-acid-o,s-diesters. These are organooxygen compounds containing a O,S-diester derivative of phosphoroamidothioic acid. They have the general structure RSP(=O)(OR')(NH2), where R,R' are organyl groups. Based on a literature review a significant number of articles have been published on (±)-Methamidophos.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Metamidophos	ChEBI
Methyl phosphoramidothioate	ChEBI
O,S-Dimethyl amidothiophosphate	ChEBI
O,S-Dimethyl phosphoramidothiolate	ChEBI
Phosphoramidothioic acid, O,S-dimethyl ester	ChEBI
Thiophosphoramidic acid O,S-dimethyl ester	ChEBI
Methyl phosphoramidothioic acid	Generator
O,S-Dimethyl amidothiophosphoric acid	Generator
O,S-Dimethyl phosphoramidothiolic acid	Generator
Phosphoramidothioate, O,S-dimethyl ester	Generator
Thiophosphoramidate O,S-dimethyl ester	Generator
Acephate-met	HMDB
Amidor	HMDB
Chevron 9006	HMDB
Chevron ortho 9006	HMDB
Filitox	HMDB
Hamidop	HMDB
Metamidofos estrella	HMDB
Methamidophos	HMDB
Methyl phosphoramidothioate ((meo)(mes)p(O)(NH2))	HMDB
Monitor	HMDB
Monitor (insecticide)	HMDB
MTD	HMDB
O,S-Dimethyl phosphoramidothioate	HMDB
O,S-Dimethyl phosphoroamidothioate	HMDB
O,S-Dimethylphosphoroamidothioate	HMDB
Ortho monitor	HMDB
Patrole	HMDB
Pillaron	HMDB
Sniper	HMDB
Tahmabon	HMDB
Tamanox	HMDB
Tamaron	HMDB

Chemical Formula

C₂H₈NO₂PS

Average Molecular Weight

141.129

Monoisotopic Molecular Weight

141.001335707

IUPAC Name

[methoxy(methylsulfanyl)phosphoryl]amine

Traditional Name

tamaron

CAS Registry Number

115182-35-9

SMILES

COP(N)(=O)SC

InChI Identifier

InChI=1S/C2H8NO2PS/c1-5-6(3,4)7-2/h1-2H3,(H2,3,4)

InChI Key

NNKVPIKMPCQWCG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphoramidothioic-acid-o,s-diesters. These are organooxygen compounds containing a O,S-diester derivative of phosphoroamidothioic acid. They have the general structure RSP(=O)(OR')(NH2), where R,R' are organyl groups.

Kingdom

Organic compounds

Super Class

Organophosphorus compounds

Class

Organothiophosphorus compounds

Sub Class

Phosphoramidothioic-acid-O,S-diesters

Direct Parent

Phosphoramidothioic-acid-O,S-diesters

Alternative Parents

Substituents

Phosphoramidothioic-acid-o,s-diester
Sulfenyl compound
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic thiophosphate (CHEBI:38721 )
organothiophosphate insecticide (CHEBI:38721 )
phosphoramide (CHEBI:38721 )
Phosphoramido insecticides (C18667 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0031803)
Hypotension (HMDB: HMDB0031803)

Blood and lymphatic system disorder

Hypoglycemia (HMDB: HMDB0031803)

Observation

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Mood disorder

Major depressive disorder (HMDB: HMDB0031803)

Neurotic, stress-related, or somatoform disorder

Anxiety (HMDB: HMDB0031803)

Coma (HMDB: HMDB0031803)

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031803)
Cytoplasm (HMDB: HMDB0031803)

Source

Endogenous

Endogenous (HMDB: HMDB0031803)

Exogenous

Food

Food (HMDB: HMDB0031803)

Synthetic

Synthetic (HMDB: HMDB0031803)

Exogenous (HMDB: HMDB0031803)

Process

Not Available

Role

Environmental role

Air pollutant (HMDB: HMDB0031803)

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
Water Solubility	30.6 g/L	ALOGPS
logP	-0.94	ALOGPS
logP	-0.32	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	15.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	31.68 m³·mol⁻¹	ChemAxon
Polarizability	12.07 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
DarkChem	[M+H]+	127.34	31661259
DarkChem	[M-H]-	122.689	31661259
DeepCCS	[M+H]+	121.579	30932474
DeepCCS	[M-H]-	119.496	30932474
DeepCCS	[M-2H]-	155.461	30932474
DeepCCS	[M+Na]+	129.987	30932474
AllCCS	[M+H]+	132.4	32859911
AllCCS	[M+H-H2O]+	128.6	32859911
AllCCS	[M+NH4]+	136.0	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	134.0	32859911
AllCCS	[M+Na-2H]-	138.1	32859911
AllCCS	[M+HCOO]-	142.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.05 minutes	32390414
Predicted by Siyang on May 30, 2022	9.1403 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.11 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	323.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	497.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	343.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	61.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	226.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	67.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	279.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	238.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	802.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	596.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	36.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	675.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	696.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	468.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	365.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-Methamidophos	COP(N)(=O)SC	1811.4	Standard polar	33892256
(??)-Methamidophos	COP(N)(=O)SC	1085.4	Standard non polar	33892256
(??)-Methamidophos	COP(N)(=O)SC	1183.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(±)-Methamidophos,1TMS,isomer #1	COP(=O)(N[Si](C)(C)C)SC	1338.9	Semi standard non polar	33892256
(±)-Methamidophos,1TMS,isomer #1	COP(=O)(N[Si](C)(C)C)SC	1275.6	Standard non polar	33892256
(±)-Methamidophos,2TMS,isomer #1	COP(=O)(SC)N([Si](C)(C)C)[Si](C)(C)C	1461.9	Semi standard non polar	33892256
(±)-Methamidophos,2TMS,isomer #1	COP(=O)(SC)N([Si](C)(C)C)[Si](C)(C)C	1511.8	Standard non polar	33892256
(±)-Methamidophos,1TBDMS,isomer #1	COP(=O)(N[Si](C)(C)C(C)(C)C)SC	1613.0	Semi standard non polar	33892256
(±)-Methamidophos,1TBDMS,isomer #1	COP(=O)(N[Si](C)(C)C(C)(C)C)SC	1550.5	Standard non polar	33892256
(±)-Methamidophos,2TBDMS,isomer #1	COP(=O)(SC)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1922.1	Semi standard non polar	33892256
(±)-Methamidophos,2TBDMS,isomer #1	COP(=O)(SC)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1933.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Methamidophos GC-MS (Non-derivatized) - 70eV, Positive	splash10-08i4-9300000000-56d4e3bc363cce753683	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Methamidophos GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Methamidophos GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 10V, Positive-QTOF	splash10-0007-7900000000-32e474674de8c15ed60a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 20V, Positive-QTOF	splash10-0005-9300000000-b1c907e2fd5c6190ef90	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 40V, Positive-QTOF	splash10-01ot-9000000000-19efb41eb42da7683de1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 10V, Negative-QTOF	splash10-000f-9700000000-bc4a47915aa2f2d4402f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 20V, Negative-QTOF	splash10-0002-9000000000-d2352d752bc864cb342c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 40V, Negative-QTOF	splash10-0a4j-9500000000-66b182cec233c6816900	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 10V, Negative-QTOF	splash10-01ox-9000000000-ac78ce24adc5437da9cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 20V, Negative-QTOF	splash10-01tc-9000000000-e3aebff85244210b523d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 40V, Negative-QTOF	splash10-06r2-9200000000-c0c6e8d9e2352da18aa8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 10V, Positive-QTOF	splash10-0006-6900000000-f28bfe26553972983789	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 20V, Positive-QTOF	splash10-0006-9600000000-551cd5d207c6e8ea8c71	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Methamidophos 40V, Positive-QTOF	splash10-03dj-9000000000-48066750a628bea43a42	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008476

KNApSAcK ID

Not Available

Chemspider ID

3954

KEGG Compound ID

C18667

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4096

PDB ID

Not Available

ChEBI ID

38721

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (±)-Methamidophos (HMDB0031803)

MOL for HMDB0031803 ((±)-Methamidophos)

3D MOL for HMDB0031803 ((±)-Methamidophos)

3D SDF for HMDB0031803 ((±)-Methamidophos)

3D-SDF for HMDB0031803 ((±)-Methamidophos)

PDB for HMDB0031803 ((±)-Methamidophos)

3D PDB for HMDB0031803 ((±)-Methamidophos)

SMILES for HMDB0031803 ((±)-Methamidophos)

INCHI for HMDB0031803 ((±)-Methamidophos)

Structure for HMDB0031803 ((±)-Methamidophos)

3D Structure for HMDB0031803 ((±)-Methamidophos)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra