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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:41:40 UTC

Update Date

2021-09-26 23:03:20 UTC

HMDB ID

HMDB0251357

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Diisopropyl methylphosphonate

Description

Diisopropyl methylphosphonate, also known as DIMP, belongs to the class of organic compounds known as dialkyl alkylphosphonates. Dialkyl alkylphosphonates are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group. Diisopropyl methylphosphonate is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Diisopropyl methylphosphonate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Diisopropyl methylphosphonate 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    HMDB0251357
HETATM    1  C1  UNL     1       1.927  -0.150   1.722  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.049  -0.157   0.212  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.286   0.630  -0.139  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.892   0.389  -0.310  1.00  0.00           O  
HETATM    5  P1  UNL     1       0.009  -0.648  -1.264  1.00  0.00           P  
HETATM    6  C4  UNL     1      -0.280   0.179  -2.868  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.689  -1.990  -1.476  1.00  0.00           O  
HETATM    8  O3  UNL     1      -1.488  -0.968  -0.541  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.851   0.013   0.372  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.936  -0.623   1.745  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.205   0.601   0.065  1.00  0.00           C  
HETATM   12  H1  UNL     1       1.261   0.697   2.034  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.450  -1.068   2.117  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.931   0.019   2.192  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.212  -1.218  -0.091  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.215   1.126  -1.126  1.00  0.00           H  
HETATM   17  H6  UNL     1       4.186  -0.027  -0.185  1.00  0.00           H  
HETATM   18  H7  UNL     1       3.508   1.426   0.600  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.401  -0.559  -3.678  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.542   0.918  -3.085  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.206   0.794  -2.820  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.042   0.761   0.384  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.631  -1.504   1.652  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.473   0.096   2.418  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.948  -0.911   2.144  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.997   0.207   0.738  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.468   0.263  -0.974  1.00  0.00           H  
HETATM   28  H17 UNL     1      -3.233   1.704   0.162  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5
CONECT    5    6    7    7    8
CONECT    6   19   20   21
CONECT    8    9
CONECT    9   10   11   22
CONECT   10   23   24   25
CONECT   11   26   27   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Bis(1-methylethyl) methylphosphonate	ChEBI
Diisopropyl methanephosphonate	ChEBI
DIMP	ChEBI
Methylphosphonic acid bis(1-methylethyl)ester	ChEBI
Bis(1-methylethyl) methylphosphonic acid	Generator
Diisopropyl methanephosphonic acid	Generator
Methylphosphonate bis(1-methylethyl)ester	Generator
Diisopropyl methylphosphonic acid	Generator
Methylphosphonate diisopropyl ester	Generator

Chemical Formula

C₇H₁₇O₃P

Average Molecular Weight

180.1818

Monoisotopic Molecular Weight

180.091530922

IUPAC Name

bis(propan-2-yl) methylphosphonate

Traditional Name

isopropyl methylphosphonate

CAS Registry Number

Not Available

SMILES

CC(C)OP(C)(=O)OC(C)C

InChI Identifier

InChI=1S/C7H17O3P/c1-6(2)9-11(5,8)10-7(3)4/h6-7H,1-5H3

InChI Key

WOAFDHWYKSOANX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkyl alkylphosphonates. Dialkyl alkylphosphonates are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Phosphonic acid diesters

Direct Parent

Dialkyl alkylphosphonates

Alternative Parents

Substituents

Dialkyl alkylphosphonate
Phosphonic acid ester
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organophosphorus compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic phosphonate (CHEBI:77325 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0251357)

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	1.02	ALOGPS
logP	1.41	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-7.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	44.48 m³·mol⁻¹	ChemAxon
Polarizability	18.51 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]+	141.555	30932474
DeepCCS	[M-H]-	139.059	30932474
DeepCCS	[M-2H]-	175.08	30932474
DeepCCS	[M+Na]+	150.012	30932474
AllCCS	[M+H]+	141.7	32859911
AllCCS	[M+H-H2O]+	138.1	32859911
AllCCS	[M+NH4]+	145.0	32859911
AllCCS	[M+Na]+	146.0	32859911
AllCCS	[M-H]-	141.0	32859911
AllCCS	[M+Na-2H]-	143.3	32859911
AllCCS	[M+HCOO]-	146.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diisopropyl methylphosphonate	CC(C)OP(C)(=O)OC(C)C	1517.1	Standard polar	33892256
Diisopropyl methylphosphonate	CC(C)OP(C)(=O)OC(C)C	1015.7	Standard non polar	33892256
Diisopropyl methylphosphonate	CC(C)OP(C)(=O)OC(C)C	1070.1	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 - Diisopropyl methylphosphonate GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-5900000000-3cbc0a2ad7e121ac0a84	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diisopropyl methylphosphonate 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 - Diisopropyl methylphosphonate 10V, Positive-QTOF	splash10-0002-9300000000-9483343cf57b0404e8a3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 20V, Positive-QTOF	splash10-0002-9100000000-0f4f78b78e76b649c7f7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 40V, Positive-QTOF	splash10-0007-9000000000-f60c278295ee826f10eb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 10V, Negative-QTOF	splash10-004i-0900000000-06abe483623c71902961	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 20V, Negative-QTOF	splash10-004i-5900000000-418a442603bd7f257a5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 40V, Negative-QTOF	splash10-004i-9200000000-4338a1f71257ceb9c35d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 10V, Positive-QTOF	splash10-000j-9800000000-b2d41c2fc677010f1457	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 20V, Positive-QTOF	splash10-0002-9000000000-27d68e801482e0c96fc7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 40V, Positive-QTOF	splash10-002f-9000000000-8436abca55a86e479b4f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 10V, Negative-QTOF	splash10-004i-1900000000-b4d91c977bd072cb4049	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 20V, Negative-QTOF	splash10-056r-7900000000-9f9658a1047fc77ee7e8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopropyl methylphosphonate 40V, Negative-QTOF	splash10-004i-9000000000-50a9a15461c0331bf281	2021-10-12	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	¹H NMR Spectrum (1D, 200 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	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	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

DB02127

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diisopropyl_methylphosphonate

METLIN ID

Not Available

PubChem Compound

3073

PDB ID

Not Available

ChEBI ID

77325

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 Diisopropyl methylphosphonate (HMDB0251357)

MOL for HMDB0251357 (Diisopropyl methylphosphonate)

3D MOL for HMDB0251357 (Diisopropyl methylphosphonate)

3D SDF for HMDB0251357 (Diisopropyl methylphosphonate)

3D-SDF for HMDB0251357 (Diisopropyl methylphosphonate)

PDB for HMDB0251357 (Diisopropyl methylphosphonate)

3D PDB for HMDB0251357 (Diisopropyl methylphosphonate)

SMILES for HMDB0251357 (Diisopropyl methylphosphonate)

INCHI for HMDB0251357 (Diisopropyl methylphosphonate)

Structure for HMDB0251357 (Diisopropyl methylphosphonate)

3D Structure for HMDB0251357 (Diisopropyl methylphosphonate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra