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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 04:00:45 UTC

Update Date

2021-09-26 23:00:26 UTC

HMDB ID

HMDB0249500

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester

Description

(R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester, also known as methylphosphonofluoridate, pinacolyl or pinacolyl methylphosphonofluoridate, belongs to the class of organic compounds known as phosphonic acid esters. These are organic compounds containing phosphonic acid ester functional group, with the general structure ROP(=O)OH (R = organyl group). Based on a literature review very few articles have been published on (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester. This compound has been identified in human blood as reported by (PMID: 31557052 ). (r)-methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester 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

COMPND    HMDB0249500
HETATM    1  C1  UNL     1      -0.460  -0.696  -2.078  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.114  -0.234  -0.760  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.048  -1.110  -0.249  1.00  0.00           O  
HETATM    4  P1  UNL     1       2.575  -0.480  -0.075  1.00  0.00           P  
HETATM    5  C3  UNL     1       2.725   0.703   1.277  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.526  -1.632   0.231  1.00  0.00           O  
HETATM    7  F1  UNL     1       3.125   0.279  -1.471  1.00  0.00           F  
HETATM    8  C4  UNL     1      -1.021   0.026   0.175  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.871  -1.196   0.428  1.00  0.00           C  
HETATM   10  C6  UNL     1      -0.597   0.586   1.499  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.933   1.056  -0.502  1.00  0.00           C  
HETATM   12  H1  UNL     1       0.251  -1.230  -2.706  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.339  -1.376  -1.937  1.00  0.00           H  
HETATM   14  H3  UNL     1      -0.869   0.209  -2.581  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.630   0.732  -0.941  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.830   0.868   1.434  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.345   1.714   0.963  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.314   0.359   2.223  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.275  -2.125   0.506  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.408  -1.066   1.395  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.686  -1.295  -0.342  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.540   0.757   2.090  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.024  -0.165   2.077  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.047   1.542   1.420  1.00  0.00           H  
HETATM   25  H14 UNL     1      -1.284   1.809  -0.979  1.00  0.00           H  
HETATM   26  H15 UNL     1      -2.661   1.475   0.211  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.471   0.489  -1.309  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    8   15
CONECT    3    4
CONECT    4    5    6    6    7
CONECT    5   16   17   18
CONECT    8    9   10   11
CONECT    9   19   20   21
CONECT   10   22   23   24
CONECT   11   25   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)-Methylphosphonofluoridate 1,2,2-trimethylpropyl ester	Generator
Methylphosphonofluoridate, pinacolyl	HMDB
Pinacolyl methylphosphonofluoridate	HMDB

Chemical Formula

C₇H₁₆FO₂P

Average Molecular Weight

182.175

Monoisotopic Molecular Weight

182.087194916

IUPAC Name

3,3-dimethylbutan-2-yl fluoro(methyl)phosphinate

Traditional Name

soman

CAS Registry Number

Not Available

SMILES

CC(OP(C)(F)=O)C(C)(C)C

InChI Identifier

InChI=1S/C7H16FO2P/c1-6(7(2,3)4)10-11(5,8)9/h6H,1-5H3

InChI Key

GRXKLBBBQUKJJZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphonic acid esters. These are organic compounds containing phosphonic acid ester functional group, with the general structure ROP(=O)OH (R = organyl group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Phosphonic acid esters

Direct Parent

Phosphonic acid esters

Alternative Parents

Substituents

Phosphonic acid ester
Alkylphosphonofluoridic acid or ester derivatives
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organophosphorus compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphonic ester (CHEBI:9195 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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	1.69	ALOGPS
logP	2.08	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-8.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	43.16 m³·mol⁻¹	ChemAxon
Polarizability	17.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	137.353	30932474
DeepCCS	[M-H]-	134.671	30932474
DeepCCS	[M-2H]-	170.535	30932474
DeepCCS	[M+Na]+	145.224	30932474
AllCCS	[M+H]+	138.9	32859911
AllCCS	[M+H-H2O]+	135.3	32859911
AllCCS	[M+NH4]+	142.3	32859911
AllCCS	[M+Na]+	143.2	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	141.5	32859911
AllCCS	[M+HCOO]-	144.0	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9100000000-5f61f676d4b93eb4dfb2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester 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 - (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester 10V, Negative-QTOF	splash10-001i-2900000000-6720b10b3b650051488d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester 20V, Negative-QTOF	splash10-004i-9100000000-8ae116234006ebea8448	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester 40V, Negative-QTOF	splash10-004i-9000000000-d554581b2af3d7b0287e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester 10V, Positive-QTOF	splash10-052r-9100000000-df46374cc80a3528ba65	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester 20V, Positive-QTOF	splash10-052k-9000000000-3e4e2876d572b9df9e48	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester 40V, Positive-QTOF	splash10-0a4i-9000000000-1df0e93e857bec41123d	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 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	¹³C NMR Spectrum (1D, 300 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	¹H NMR Spectrum (1D, 400 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	¹³C NMR Spectrum (1D, 500 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, 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	¹³C NMR Spectrum (1D, 800 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, 900 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

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

C00002958

Chemspider ID

7032

KEGG Compound ID

C07494

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7305

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1637111

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 (R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester (HMDB0249500)

MOL for HMDB0249500 ((R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester)

3D MOL for HMDB0249500 ((R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester)

3D SDF for HMDB0249500 ((R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester)

3D-SDF for HMDB0249500 ((R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester)

PDB for HMDB0249500 ((R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester)

3D PDB for HMDB0249500 ((R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester)

SMILES for HMDB0249500 ((R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester)

INCHI for HMDB0249500 ((R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester)

Structure for HMDB0249500 ((R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester)

3D Structure for HMDB0249500 ((R)-Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra