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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-04-16 20:46:37 UTC

Update Date

2023-02-21 17:30:25 UTC

HMDB ID

HMDB0061711

Secondary Accession Numbers

HMDB61711

Metabolite Identification

Common Name

Methylphosphate

Description

Methylphosphate, also known as monomethyl phosphate or MMP, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Methylphosphate is a moderately acidic compound (based on its pKa). Methylphosphate is a methyl ester of phosphoric acid. It is a colourless, nonvolatile liquid, and it has some specialized uses in the production of other compounds.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Dihydrogen methyl phosphate	ChEBI
Methyl phosphate	ChEBI
MMP	ChEBI
Monomethyl dihydrogen phosphate	ChEBI
Monomethyl phosphate	ChEBI
O-Methyl phosphate	ChEBI
Phosphoric acid monomethyl ester	ChEBI
Dihydrogen methyl phosphoric acid	Generator
Methyl phosphoric acid	Generator
Monomethyl dihydrogen phosphoric acid	Generator
Monomethyl phosphoric acid	Generator
O-Methyl phosphoric acid	Generator
Phosphate monomethyl ester	Generator
Methylphosphoric acid	Generator
Methyl dihydrogen phosphoric acid	Generator
Methylphosphate	MeSH
Methyl dihydrogen phosphate	HMDB

Chemical Formula

CH₅O₄P

Average Molecular Weight

112.0218

Monoisotopic Molecular Weight

111.99254516

IUPAC Name

methoxyphosphonic acid

Traditional Name

methyl phosphate

CAS Registry Number

812-00-0

SMILES

COP(O)(O)=O

InChI Identifier

InChI=1S/CH5O4P/c1-5-6(2,3)4/h1H3,(H2,2,3,4)

InChI Key

CAAULPUQFIIOTL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:340824 )
monoalkyl phosphate (CHEBI:340824 )

Ontology

Not Available

Placenta (HMDB: HMDB0061711)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

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
Water Solubility	25.4 g/L	ALOGPS
logP	-0.83	ALOGPS
logP	-0.64	ChemAxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	19.13 m³·mol⁻¹	ChemAxon
Polarizability	7.78 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]+	120.779	31661259
DarkChem	[M-H]-	114.579	31661259
DeepCCS	[M+H]+	123.607	30932474
DeepCCS	[M-H]-	120.81	30932474
DeepCCS	[M-2H]-	157.359	30932474
DeepCCS	[M+Na]+	131.854	30932474
AllCCS	[M+H]+	131.0	32859911
AllCCS	[M+H-H2O]+	126.8	32859911
AllCCS	[M+NH4]+	134.9	32859911
AllCCS	[M+Na]+	136.0	32859911
AllCCS	[M-H]-	128.2	32859911
AllCCS	[M+Na-2H]-	133.0	32859911
AllCCS	[M+HCOO]-	138.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methylphosphate	COP(O)(O)=O	1918.0	Standard polar	33892256
Methylphosphate	COP(O)(O)=O	945.5	Standard non polar	33892256
Methylphosphate	COP(O)(O)=O	979.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methylphosphate,1TMS,isomer #1	COP(=O)(O)O[Si](C)(C)C	1131.7	Semi standard non polar	33892256
Methylphosphate,1TMS,isomer #1	COP(=O)(O)O[Si](C)(C)C	1054.6	Standard non polar	33892256
Methylphosphate,1TMS,isomer #1	COP(=O)(O)O[Si](C)(C)C	1473.7	Standard polar	33892256
Methylphosphate,2TMS,isomer #1	COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1159.3	Semi standard non polar	33892256
Methylphosphate,2TMS,isomer #1	COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1193.9	Standard non polar	33892256
Methylphosphate,2TMS,isomer #1	COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1199.4	Standard polar	33892256
Methylphosphate,1TBDMS,isomer #1	COP(=O)(O)O[Si](C)(C)C(C)(C)C	1383.4	Semi standard non polar	33892256
Methylphosphate,1TBDMS,isomer #1	COP(=O)(O)O[Si](C)(C)C(C)(C)C	1308.4	Standard non polar	33892256
Methylphosphate,1TBDMS,isomer #1	COP(=O)(O)O[Si](C)(C)C(C)(C)C	1636.3	Standard polar	33892256
Methylphosphate,2TBDMS,isomer #1	COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1590.1	Semi standard non polar	33892256
Methylphosphate,2TBDMS,isomer #1	COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1629.1	Standard non polar	33892256
Methylphosphate,2TBDMS,isomer #1	COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1502.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methylphosphate GC-MS (2 TMS)	splash10-006x-5970000000-fcc443640104212f1139	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methylphosphate GC-EI-TOF (Non-derivatized)	splash10-0006-2980000000-b4d7b5ebf204117f6515	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylphosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-01pk-9300000000-918effdaa1b9356128cb	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylphosphate 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 - Methylphosphate 10V, Positive-QTOF	splash10-03di-1900000000-d740450d843ea2f52c26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 20V, Positive-QTOF	splash10-03dl-6900000000-71637f039f67a5862b03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 40V, Positive-QTOF	splash10-01ox-9100000000-b53fe76315a7d15c7af7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 10V, Negative-QTOF	splash10-03di-3900000000-55e568ee97a2e0545856	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 20V, Negative-QTOF	splash10-004i-9100000000-d90c3bc681f7a6ed1ab4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 40V, Negative-QTOF	splash10-004i-9000000000-ee2a540d9df1d610ef7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 10V, Negative-QTOF	splash10-01t9-9500000000-1145ff1a0d8abfbb3eb5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 20V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 40V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 10V, Positive-QTOF	splash10-03di-0900000000-2497cf97e89f44531fb9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 20V, Positive-QTOF	splash10-03di-8900000000-29c2837fe7cb77943888	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphosphate 40V, Positive-QTOF	splash10-01q9-9000000000-4211979ebbb9c458a9c0	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)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Not Available

Biospecimen Locations

Feces

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

12578

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13130

PDB ID

Not Available

ChEBI ID

340824

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

Morita CT, Beckman EM, Bukowski JF, Tanaka Y, Band H, Bloom BR, Golan DE, Brenner MB: Direct presentation of nonpeptide prenyl pyrophosphate antigens to human gamma delta T cells. Immunity. 1995 Oct;3(4):495-507. [PubMed:7584140 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Methylphosphate (HMDB0061711)

MOL for HMDB0061711 (Methylphosphate)

3D MOL for HMDB0061711 (Methylphosphate)

3D SDF for HMDB0061711 (Methylphosphate)

3D-SDF for HMDB0061711 (Methylphosphate)

PDB for HMDB0061711 (Methylphosphate)

3D PDB for HMDB0061711 (Methylphosphate)

SMILES for HMDB0061711 (Methylphosphate)

INCHI for HMDB0061711 (Methylphosphate)

Structure for HMDB0061711 (Methylphosphate)

3D Structure for HMDB0061711 (Methylphosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra