MiMeDB: Showing metabocard for aminomethylphosphonic acid (MMDBc0054346)

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:07:59 UTC

Update Date

2025-10-07 16:04:18 UTC

Metabolite ID

MMDBc0054346

Metabolite Identification

Common Name

aminomethylphosphonic acid

Description

Aminomethylphosphonic acid is a phosphonic acid derivative and a key metabolite of glyphosate, widely recognized for its persistence in the environment, particularly in soil and water. Its chemical structure features an aminomethyl group attached to a phosphonic acid moiety, which contributes to its stability and resistance to degradation. Following the application of glyphosate herbicides, a significant portion degrades into aminomethylphosphonic acid, which is notably more persistent than glyphosate itself (PMID:40914222 ). In biological contexts, aminomethylphosphonic acid has been linked to various metabolic pathways, including associations with DNA damage biomarkers in rural populations exposed to glyphosate (PMID:40974630 ). Studies have also explored the effects of aminomethylphosphonic acid on liver metabolomics in hatchlings of invasive turtles, indicating potential impacts on embryonic development (PMID:40848207 ). Furthermore, advancements in analytical methods have enabled the detection of aminomethylphosphonic acid in environmental samples, underscoring its relevance in ecological studies (PMID:40784480 ). As a dual-functional molecule, it has also been utilized in interface engineering strategies to influence charge transport and crystallization dynamics (PMID:40762028 ).

Structure

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

Synonyms

Value	Source
1-Aminomethylphosphonic acid	ChEBI
AMPA	ChEBI
Aminomethylphosphonate	Kegg
1-Aminomethylphosphonate	Generator
(Aminomethyl)phosphonate	HMDB
1-Aminomethylphosphonic acid, calcium salt	HMDB
1-Aminomethylphosphonic acid, disodium salt	HMDB
1-Aminomethylphosphonic acid, sulfate (2:1)	HMDB
1-Aminomethylphosphonic acid, ammonium salt	HMDB
1-Aminomethylphosphonic acid, magnesium salt	HMDB
1-Aminomethylphosphonic acid, potassium salt	HMDB
AMeP	HMDB
1-Aminomethylphosphonic acid, hydrochloride	HMDB
1-Aminomethylphosphonic acid, monosulfate	HMDB
1-Aminomethylphosphonic acid, sodium salt	HMDB
Aminomethylphosphonic acid	Generator

Molecular Formula

CH₆NO₃P

Average Mass

111.037

Monoisotopic Mass

111.008529575

IUPAC Name

(aminomethyl)phosphonic acid

Traditional Name

aminomethylphosphonic acid

CAS Registry Number

Not Available

SMILES

NCP(O)(O)=O

InChI Identifier

InChI=1S/CH6NO3P/c2-1-6(3,4)5/h1-2H2,(H2,3,4,5)

InChI Key

MGRVRXRGTBOSHW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Organic phosphonic acids

Direct Parent

Organic phosphonic acids

Alternative Parents

Substituents

Organophosphonic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organophosphorus compound
Organonitrogen compound
Primary aliphatic amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:28812 )
phosphonic acids (CHEBI:28812 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	29.4 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.8	ChemAxon
logS	-0.58	ALOGPS
pKa (Strongest Acidic)	-0.2	ChemAxon
pKa (Strongest Basic)	9.94	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	20.5 m³·mol⁻¹	ChemAxon
Polarizability	8.17 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-2900000000-b09aa10d51af8e400f77	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-9200000000-18dc86029350d2f26772	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lu-9100000000-40c583a7d4d737d0e4f8	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03gi-9300000000-3f16daf7bba65c555d84	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9300000000-8ab973d5962592196137	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-9000000000-267b6aa78b7d463ddd8c	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01t9-9400000000-fe08277a3700826259a7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-5cfcc2476cb245ed6d3b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fr-9000000000-e7b7a7c1bbbb8167b8d8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-8edd13b80c14ee028554	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-1d00acc29c81a18b2b30	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-9000000000-1cbbfe561e70cec74529	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	544.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	438.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	40.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (void)	2025-10-24	240.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (void)	2025-10-24	257.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	350.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	434.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	898.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	786.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	232.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	584.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	254.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	61.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	438.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	813.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	160.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	382.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	573.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	554.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	aminomethylphosphonic acid_TMS_1	C[Si](C)(C)OP(=O)(O)CN	standard non polar	2025-10-24	1807.14
Gas Chromatography	aminomethylphosphonic acid_TMS_2	C[Si](C)(C)NCP(=O)(O)O	standard non polar	2025-10-24	1519.05
Gas Chromatography	aminomethylphosphonic acid_TMS_3	C[Si](C)(C)OP(=O)(CN)O[Si](C)(C)C	standard non polar	2025-10-24	2294.81
Gas Chromatography	aminomethylphosphonic acid_TMS_4	C[Si](C)(C)NCP(=O)(O)O[Si](C)(C)C	standard non polar	2025-10-24	1858.53
Gas Chromatography	aminomethylphosphonic acid_TMS_5	C[Si](C)(C)N(CP(=O)(O)O)[Si](C)(C)C	standard non polar	2025-10-24	2048.03
Gas Chromatography	aminomethylphosphonic acid_TMS_6	C[Si](C)(C)NCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1833.45
Gas Chromatography	aminomethylphosphonic acid_TMS_7	C[Si](C)(C)OP(=O)(O)CN([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2048.55
Gas Chromatography	aminomethylphosphonic acid_TMS_8	C[Si](C)(C)OP(=O)(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2267.72
Gas Chromatography	aminomethylphosphonic acid_TMS_1	C[Si](C)(C)OP(=O)(O)CN	standard polar	2025-10-24	2218.9
Gas Chromatography	aminomethylphosphonic acid_TMS_2	C[Si](C)(C)NCP(=O)(O)O	standard polar	2025-10-24	1975.86
Gas Chromatography	aminomethylphosphonic acid_TMS_3	C[Si](C)(C)OP(=O)(CN)O[Si](C)(C)C	standard polar	2025-10-24	2077.65
Gas Chromatography	aminomethylphosphonic acid_TMS_4	C[Si](C)(C)NCP(=O)(O)O[Si](C)(C)C	standard polar	2025-10-24	2169.61
Gas Chromatography	aminomethylphosphonic acid_TMS_5	C[Si](C)(C)N(CP(=O)(O)O)[Si](C)(C)C	standard polar	2025-10-24	1571.03
Gas Chromatography	aminomethylphosphonic acid_TMS_6	C[Si](C)(C)NCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1635.41
Gas Chromatography	aminomethylphosphonic acid_TMS_7	C[Si](C)(C)OP(=O)(O)CN([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1898.47
Gas Chromatography	aminomethylphosphonic acid_TMS_8	C[Si](C)(C)OP(=O)(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2363.66

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	1	Human
Bacteria/Eubacteria	Proteobacteria	1	Human
Bacteria/Eubacteria	Firmicutes	2	Human feces

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Water	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0240707

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13399

KEGG Compound ID

C11033

BioCyc ID

CPD0-1074

BiGG ID

Not Available

Wikipedia Link

Aminomethylphosphonic_acid

METLIN ID

Not Available

PubChem Compound

14017

PDB ID

Not Available

ChEBI ID

28812

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for aminomethylphosphonic acid (MMDBc0054346)

MOL for #<Metabolite:0x00007f9acfae8910>

3D MOL for #<Metabolite:0x00007f9acfae8910>

3D SDF for #<Metabolite:0x00007f9acfae8910>

3D-SDF for #<Metabolite:0x00007f9acfae8910>

PDB for #<Metabolite:0x00007f9acfae8910>

3D PDB for #<Metabolite:0x00007f9acfae8910>

SMILES for #<Metabolite:0x00007f9acfae8910>

INCHI for #<Metabolite:0x00007f9acfae8910>

Structure for #<Metabolite:0x00007f9acfae8910>

3D Structure for #<Metabolite:0x00007f9acfae8910>