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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:55:36 UTC

Update Date

2021-09-26 23:01:08 UTC

HMDB ID

HMDB0249961

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Aminophenyl phosphate

Description

4-Aminophenyl phosphate, also known as 4-aminophenol or 4-aminophenol, 18O-labeled, 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. Based on a literature review a significant number of articles have been published on 4-Aminophenyl phosphate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-aminophenyl phosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Aminophenyl 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

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0       2.667  -3.080   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.897  -4.414   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.437  -1.746   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Aminophenyl phosphoric acid	Generator
4-Aminophenol	HMDB
4-Aminophenol conjugate monoacid	HMDB
4-Aminophenol hydrochloride	HMDB
4-Aminophenol monopotassium salt	HMDB
4-Aminophenol monosodium salt	HMDB
4-Aminophenol sulfate	HMDB
4-Aminophenol sulfate (2:1)	HMDB
4-Aminophenol, 18O-labeled	HMDB
4-Aminophenol, 3H-labeled	HMDB
4-Aminophenol, ion(1+)	HMDB
4-Hydroxyaniline	HMDB
p-Aminophenol	HMDB
p-Aminophenol phosphate	HMDB
Para-aminophenol	HMDB

Chemical Formula

C₆H₈NO₄P

Average Molecular Weight

189.107

Monoisotopic Molecular Weight

189.01909474

IUPAC Name

(4-aminophenoxy)phosphonic acid

Traditional Name

4-aminophenoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

NC1=CC=C(OP(O)(O)=O)C=C1

InChI Identifier

InChI=1S/C6H8NO4P/c7-5-1-3-6(4-2-5)11-12(8,9)10/h1-4H,7H2,(H2,8,9,10)

InChI Key

FXZCCINCKDATPA-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
Aniline or substituted anilines
Benzenoid
Monocyclic benzene moiety
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	-0.06	ALOGPS
logP	-0.074	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.13	ChemAxon
pKa (Strongest Basic)	4.06	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.61 m³·mol⁻¹	ChemAxon
Polarizability	15.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	130.089	30932474
DeepCCS	[M-H]-	127.389	30932474
DeepCCS	[M-2H]-	163.662	30932474
DeepCCS	[M+Na]+	138.908	30932474
AllCCS	[M+H]+	143.4	32859911
AllCCS	[M+H-H2O]+	139.4	32859911
AllCCS	[M+NH4]+	147.1	32859911
AllCCS	[M+Na]+	148.2	32859911
AllCCS	[M-H]-	134.4	32859911
AllCCS	[M+Na-2H]-	135.6	32859911
AllCCS	[M+HCOO]-	137.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Aminophenyl phosphate	NC1=CC=C(OP(O)(O)=O)C=C1	3299.4	Standard polar	33892256
4-Aminophenyl phosphate	NC1=CC=C(OP(O)(O)=O)C=C1	1847.0	Standard non polar	33892256
4-Aminophenyl phosphate	NC1=CC=C(OP(O)(O)=O)C=C1	1935.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Aminophenyl phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OC1=CC=C(N)C=C1	1911.9	Semi standard non polar	33892256
4-Aminophenyl phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OC1=CC=C(N)C=C1	1911.6	Standard non polar	33892256
4-Aminophenyl phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OC1=CC=C(N)C=C1	2653.6	Standard polar	33892256
4-Aminophenyl phosphate,1TMS,isomer #2	C[Si](C)(C)NC1=CC=C(OP(=O)(O)O)C=C1	2118.8	Semi standard non polar	33892256
4-Aminophenyl phosphate,1TMS,isomer #2	C[Si](C)(C)NC1=CC=C(OP(=O)(O)O)C=C1	2008.2	Standard non polar	33892256
4-Aminophenyl phosphate,1TMS,isomer #2	C[Si](C)(C)NC1=CC=C(OP(=O)(O)O)C=C1	2519.6	Standard polar	33892256
4-Aminophenyl phosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C(N)C=C1)O[Si](C)(C)C	1958.6	Semi standard non polar	33892256
4-Aminophenyl phosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C(N)C=C1)O[Si](C)(C)C	2009.3	Standard non polar	33892256
4-Aminophenyl phosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C(N)C=C1)O[Si](C)(C)C	2383.2	Standard polar	33892256
4-Aminophenyl phosphate,2TMS,isomer #2	C[Si](C)(C)NC1=CC=C(OP(=O)(O)O[Si](C)(C)C)C=C1	2051.7	Semi standard non polar	33892256
4-Aminophenyl phosphate,2TMS,isomer #2	C[Si](C)(C)NC1=CC=C(OP(=O)(O)O[Si](C)(C)C)C=C1	2062.4	Standard non polar	33892256
4-Aminophenyl phosphate,2TMS,isomer #2	C[Si](C)(C)NC1=CC=C(OP(=O)(O)O[Si](C)(C)C)C=C1	2265.6	Standard polar	33892256
4-Aminophenyl phosphate,2TMS,isomer #3	C[Si](C)(C)N(C1=CC=C(OP(=O)(O)O)C=C1)[Si](C)(C)C	2084.8	Semi standard non polar	33892256
4-Aminophenyl phosphate,2TMS,isomer #3	C[Si](C)(C)N(C1=CC=C(OP(=O)(O)O)C=C1)[Si](C)(C)C	2097.2	Standard non polar	33892256
4-Aminophenyl phosphate,2TMS,isomer #3	C[Si](C)(C)N(C1=CC=C(OP(=O)(O)O)C=C1)[Si](C)(C)C	2368.9	Standard polar	33892256
4-Aminophenyl phosphate,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C1	2040.1	Semi standard non polar	33892256
4-Aminophenyl phosphate,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C1	2106.9	Standard non polar	33892256
4-Aminophenyl phosphate,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C1	2115.7	Standard polar	33892256
4-Aminophenyl phosphate,3TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2017.2	Semi standard non polar	33892256
4-Aminophenyl phosphate,3TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2145.0	Standard non polar	33892256
4-Aminophenyl phosphate,3TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2168.9	Standard polar	33892256
4-Aminophenyl phosphate,4TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C	2043.6	Semi standard non polar	33892256
4-Aminophenyl phosphate,4TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C	2167.7	Standard non polar	33892256
4-Aminophenyl phosphate,4TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C	2072.5	Standard polar	33892256
4-Aminophenyl phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C(N)C=C1	2147.2	Semi standard non polar	33892256
4-Aminophenyl phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C(N)C=C1	2124.4	Standard non polar	33892256
4-Aminophenyl phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C(N)C=C1	2729.2	Standard polar	33892256
4-Aminophenyl phosphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(OP(=O)(O)O)C=C1	2353.3	Semi standard non polar	33892256
4-Aminophenyl phosphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(OP(=O)(O)O)C=C1	2211.4	Standard non polar	33892256
4-Aminophenyl phosphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(OP(=O)(O)O)C=C1	2595.9	Standard polar	33892256
4-Aminophenyl phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C(N)C=C1)O[Si](C)(C)C(C)(C)C	2421.1	Semi standard non polar	33892256
4-Aminophenyl phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C(N)C=C1)O[Si](C)(C)C(C)(C)C	2436.9	Standard non polar	33892256
4-Aminophenyl phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C(N)C=C1)O[Si](C)(C)C(C)(C)C	2555.4	Standard polar	33892256
4-Aminophenyl phosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C=C1	2510.3	Semi standard non polar	33892256
4-Aminophenyl phosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C=C1	2486.1	Standard non polar	33892256
4-Aminophenyl phosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C=C1	2506.3	Standard polar	33892256
4-Aminophenyl phosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=C(OP(=O)(O)O)C=C1)[Si](C)(C)C(C)(C)C	2575.5	Semi standard non polar	33892256
4-Aminophenyl phosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=C(OP(=O)(O)O)C=C1)[Si](C)(C)C(C)(C)C	2482.9	Standard non polar	33892256
4-Aminophenyl phosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=C(OP(=O)(O)O)C=C1)[Si](C)(C)C(C)(C)C	2532.7	Standard polar	33892256
4-Aminophenyl phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2695.9	Semi standard non polar	33892256
4-Aminophenyl phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2710.1	Standard non polar	33892256
4-Aminophenyl phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2502.8	Standard polar	33892256
4-Aminophenyl phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2739.0	Semi standard non polar	33892256
4-Aminophenyl phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2736.3	Standard non polar	33892256
4-Aminophenyl phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2507.0	Standard polar	33892256
4-Aminophenyl phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2917.2	Semi standard non polar	33892256
4-Aminophenyl phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2927.4	Standard non polar	33892256
4-Aminophenyl phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2506.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Aminophenyl phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4s-5900000000-a6e4d77677dc01baf609	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Aminophenyl 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminophenyl phosphate 10V, Positive-QTOF	splash10-0006-0900000000-4efa101d3b57f0bbc51a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminophenyl phosphate 20V, Positive-QTOF	splash10-0006-0900000000-6fe275aeb72b8b6f7dd2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminophenyl phosphate 40V, Positive-QTOF	splash10-029x-9100000000-a9190d94299fa53c5a3f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminophenyl phosphate 10V, Negative-QTOF	splash10-004i-9000000000-156d93f9904bbe73ed59	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminophenyl phosphate 20V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminophenyl phosphate 40V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-10-12	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

Not Available

Chemspider ID

109035

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122271

PDB ID

Not Available

ChEBI ID

Not Available

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 4-Aminophenyl phosphate (HMDB0249961)

MOL for HMDB0249961 (4-Aminophenyl phosphate)

3D MOL for HMDB0249961 (4-Aminophenyl phosphate)

3D SDF for HMDB0249961 (4-Aminophenyl phosphate)

3D-SDF for HMDB0249961 (4-Aminophenyl phosphate)

PDB for HMDB0249961 (4-Aminophenyl phosphate)

3D PDB for HMDB0249961 (4-Aminophenyl phosphate)

SMILES for HMDB0249961 (4-Aminophenyl phosphate)

INCHI for HMDB0249961 (4-Aminophenyl phosphate)

Structure for HMDB0249961 (4-Aminophenyl phosphate)

3D Structure for HMDB0249961 (4-Aminophenyl phosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra