Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:54:14 UTC

Update Date

2021-09-26 23:12:05 UTC

HMDB ID

HMDB0256445

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phenyl dihydrogen phosphate

Description

Phenylphosphate belongs to the class of organic compounds known as phenyl phosphates. These are aromatic organooxygen compounds containing a phosphate group, which is O-esterified with a phenyl group. Phenylphosphate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Phenylphosphate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phenyl dihydrogen phosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Phenyl dihydrogen phosphate 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
Monophenylphosphate	ChEBI
Phenolic phosphate	ChEBI
Phenylphosphoric acid	ChEBI
Phosphoric acid, monophenyl ester	ChEBI
Monophenylphosphoric acid	Generator
Phenolic phosphoric acid	Generator
Phosphate, monophenyl ester	Generator
Phenylphosphate, disodium salt	MeSH
Phenylphosphate, dipotassium salt	MeSH
Phenylphosphate, ion (2-)	MeSH
Phenylphosphate, monopotassium salt	MeSH
Phenylphosphate	ChEBI
Phenyl phosphoric acid	Generator

Chemical Formula

C₆H₇O₄P

Average Molecular Weight

174.0911

Monoisotopic Molecular Weight

174.008195224

IUPAC Name

phenoxyphosphonic acid

Traditional Name

phenylphosphate

CAS Registry Number

Not Available

SMILES

OP(O)(=O)OC1=CC=CC=C1

InChI Identifier

InChI=1S/C6H7O4P/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)

InChI Key

CMPQUABWPXYYSH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl phosphates. These are aromatic organooxygen compounds containing a phosphate group, which is O-esterified with a phenyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Phenyl phosphates

Alternative Parents

Substituents

Phenyl phosphate
Phenoxy compound
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aryl phosphate (CHEBI:37548 )

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	0.67	ALOGPS
logP	1.02	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.79	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	2	ChemAxon
Refractivity	38.91 m³·mol⁻¹	ChemAxon
Polarizability	14.19 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	103.697	30932474
DeepCCS	[M-H]-	99.984	30932474
DeepCCS	[M-2H]-	137.727	30932474
DeepCCS	[M+Na]+	113.042	30932474
AllCCS	[M+H]+	137.2	32859911
AllCCS	[M+H-H2O]+	132.8	32859911
AllCCS	[M+NH4]+	141.3	32859911
AllCCS	[M+Na]+	142.4	32859911
AllCCS	[M-H]-	129.8	32859911
AllCCS	[M+Na-2H]-	131.1	32859911
AllCCS	[M+HCOO]-	132.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenyl dihydrogen phosphate	OP(O)(=O)OC1=CC=CC=C1	2379.2	Standard polar	33892256
Phenyl dihydrogen phosphate	OP(O)(=O)OC1=CC=CC=C1	1427.9	Standard non polar	33892256
Phenyl dihydrogen phosphate	OP(O)(=O)OC1=CC=CC=C1	1561.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenyl dihydrogen phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OC1=CC=CC=C1	1494.1	Semi standard non polar	33892256
Phenyl dihydrogen phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OC1=CC=CC=C1	1550.4	Standard non polar	33892256
Phenyl dihydrogen phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OC1=CC=CC=C1	1928.7	Standard polar	33892256
Phenyl dihydrogen phosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=CC=C1)O[Si](C)(C)C	1505.0	Semi standard non polar	33892256
Phenyl dihydrogen phosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=CC=C1)O[Si](C)(C)C	1647.0	Standard non polar	33892256
Phenyl dihydrogen phosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=CC=C1)O[Si](C)(C)C	1752.6	Standard polar	33892256
Phenyl dihydrogen phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=CC=C1	1738.5	Semi standard non polar	33892256
Phenyl dihydrogen phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=CC=C1	1773.8	Standard non polar	33892256
Phenyl dihydrogen phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=CC=C1	2101.7	Standard polar	33892256
Phenyl dihydrogen phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	1938.9	Semi standard non polar	33892256
Phenyl dihydrogen phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2063.0	Standard non polar	33892256
Phenyl dihydrogen phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2065.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenyl dihydrogen phosphate GC-EI-TOF (Non-derivatized)	splash10-01p9-2891000000-e37a5c165b555c9aee43	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenyl dihydrogen phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-006w-9400000000-f20da8de0d0ccb24c2f2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenyl dihydrogen phosphate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate LC-ESI-QQ , negative-QTOF	splash10-00fr-5900000000-7551784761881028ac35	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-b98ca16de2cca2c926b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-5ad20d90b6714cc35dbf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-9cb2fefadcb1731e3384	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-b7d118daff9fa001d2cd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate LC-ESI-QQ , positive-QTOF	splash10-0a4i-0900000000-4528fa033369efb85555	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate LC-ESI-QQ , positive-QTOF	splash10-053r-1900000000-0c431114e864fde60cdb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate LC-ESI-QQ , positive-QTOF	splash10-00lr-3900000000-f84099310300fe9824f2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate LC-ESI-QQ , positive-QTOF	splash10-0159-4900000000-873a33370f85ee2b2525	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate LC-ESI-QQ , positive-QTOF	splash10-014u-9500000000-b1fa95f3fe9d70a6f780	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate 35V, Negative-QTOF	splash10-004i-9000000000-1f84920bd3219dfd50aa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate 35V, Positive-QTOF	splash10-004i-9200000000-ad773636ed112565c058	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenyl dihydrogen phosphate 10V, Positive-QTOF	splash10-004i-0900000000-e79ccba868d3ad6dbc14	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl dihydrogen phosphate 10V, Positive-QTOF	splash10-004i-0900000000-6c11d80d408f686407e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl dihydrogen phosphate 20V, Positive-QTOF	splash10-004i-0900000000-900f61fe0476f10532ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl dihydrogen phosphate 40V, Positive-QTOF	splash10-0f6y-9100000000-c7763e911cb7d2580814	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl dihydrogen phosphate 10V, Negative-QTOF	splash10-004i-9400000000-4e2705e3045363184592	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl dihydrogen phosphate 20V, Negative-QTOF	splash10-004i-9100000000-c52dc8fd0ac28e0dcdf0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl dihydrogen phosphate 40V, Negative-QTOF	splash10-004i-9000000000-8d742ab79df185efad80	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)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	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

DB03298

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

12267

KEGG Compound ID

C02734

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

37548

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 Phenyl dihydrogen phosphate (HMDB0256445)

MOL for HMDB0256445 (Phenyl dihydrogen phosphate)

3D MOL for HMDB0256445 (Phenyl dihydrogen phosphate)

3D SDF for HMDB0256445 (Phenyl dihydrogen phosphate)

3D-SDF for HMDB0256445 (Phenyl dihydrogen phosphate)

PDB for HMDB0256445 (Phenyl dihydrogen phosphate)

3D PDB for HMDB0256445 (Phenyl dihydrogen phosphate)

SMILES for HMDB0256445 (Phenyl dihydrogen phosphate)

INCHI for HMDB0256445 (Phenyl dihydrogen phosphate)

Structure for HMDB0256445 (Phenyl dihydrogen phosphate)

3D Structure for HMDB0256445 (Phenyl dihydrogen phosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra