MiMeDB: Showing metabocard for phosphinothricin (MMDBc0054635)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:21:55 UTC

Update Date

2024-04-30 20:54:59 UTC

Metabolite ID

MMDBc0054635

Metabolite Identification

Common Name

phosphinothricin

Description

Glufosinate, also known as phosphinothricin or glufosinic acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Glufosinate or its ammonium salt Glufosinate is an active ingredient in several nonselective systemic herbicides such as Basta, Rely, Finale, Ignite, Challenge, and Liberty. Glufosinate irreversibly inhibits the enzyme glutamine synthetase, which decreases ammonia detoxification. Glufosinate is a very strong basic compound (based on its pKa). Glufosinate is a potentially toxic compound. Glufosinate-treated plants die due to a buildup of ammonia and a cessation of photosynthesis due to lack of glutamine. It interferes with the glutamine biosynthetic pathway that binds to the glutamate site of the enzyme. Increased ammonia levels lead to impairment of photorespiration and photosynthesis in plants.

Structure

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

Synonyms

Value	Source
Phosphinothricin	ChEBI
2-Amino-4-(hydroxymethylphosphinyl)butanoic acid	Kegg
2-Amino-4-(hydroxymethylphosphinyl)butanoate	Generator
Glufosinic acid	Generator
Glufosinate-ammonium	MeSH
Phosphinothricin, monoammonium salt	MeSH
Phosphinothricin, monosodium salt, (S)-isomer	MeSH
Phosphinothricin hydrochloride, (S)-isomer	MeSH
Phosphinothricin, sodium salt, (S)-isomer	MeSH
Phosphinothricin, barium (1:1) salt, (+-)-isomer	MeSH
Phosphinothricin, monoammonium salt, (S)-isomer	MeSH
Phosphinothricin, copper (+2) salt	MeSH
Phosphinothricin, disodium salt, (S)-isomer	MeSH
Phosphinothricin, monosodium salt	MeSH
Phosphinothricin, dipotassium salt, (S)-isomer	MeSH
Glufosinate ammonium	MeSH
Phosphinothricin, disodium salt	MeSH
Basta	MeSH
Phosphinothricin, monopotassium salt, (S)-isomer	MeSH
2-Amino-4-methylphosphinobutyric acid	MeSH
Ammonium glufosinate	MeSH
Ammonium-DL-homoalanine-4-yl(methyl)-phosphinate	MeSH
DL-Glufosinate	MeSH
Phosphinothricin hydrochloride	MeSH
Phosphinothricin, (S)-isomer	MeSH
Phosphinothricin, calcium (2:1) salt, (S)-isomer	MeSH
Glufosinate-p	MeSH
Phosphinothricin, diammonium salt	MeSH
3-amino-3-Carboxypropylmethylphosphinic acid	ChEBI
DL-2-amino-4-(methylphosphino)Butanoic acid	ChEBI
3-amino-3-Carboxypropylmethylphosphinate	Generator
DL-2-amino-4-(methylphosphino)Butanoate	Generator

Molecular Formula

C₅H₁₂NO₄P

Average Mass

181.1268

Monoisotopic Mass

181.050394389

IUPAC Name

2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid

Traditional Name

basta

CAS Registry Number

Not Available

SMILES

CP(O)(=O)CCC(N)C(O)=O

InChI Identifier

InChI=1S/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)

InChI Key

IAJOBQBIJHVGMQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Fatty acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Primary amine
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphinic acids (CHEBI:52136 )
Organophosphorus herbicides (C05042 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	46.3 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.8	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	39.66 m³·mol⁻¹	ChemAxon
Polarizability	16.14 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	splash10-004u-9600000000-245a60809785c5c4f3bf	2021-09-24	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-1900000000-c7a5f699586b196f06f4	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-4900000000-8ef3a4c2f4e0aa5fc416	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-49e8c42d44e715d5a703	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-1dca53897016d68f3528	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-8900000000-6d12f583f73568ac0f27	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-f0f80d3c8b20aaf97825	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1900000000-5bd7deb0296620c0b8db	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00n0-8900000000-03ae1e1af07a1601068f	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-ce716a0e41365b74c382	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-79a7d1c3ffdb6c8d4160	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9100000000-ef89dea95891e7b5e045	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-9000000000-59f39b49cb1bd5df66ed	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-10-13	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Metabolic Reactions

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	Actinobacteria	3
Bacteria	Firmicutes	1	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000797

Chemspider ID

Not Available

KEGG Compound ID

C05042

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glufosinate

METLIN ID

Not Available

PubChem Compound

4794

PDB ID

Not Available

ChEBI ID

142851

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 phosphinothricin (MMDBc0054635)

MOL for #<Metabolite:0x00007fed158ef0f8>

3D MOL for #<Metabolite:0x00007fed158ef0f8>

3D SDF for #<Metabolite:0x00007fed158ef0f8>

3D-SDF for #<Metabolite:0x00007fed158ef0f8>

PDB for #<Metabolite:0x00007fed158ef0f8>

3D PDB for #<Metabolite:0x00007fed158ef0f8>

SMILES for #<Metabolite:0x00007fed158ef0f8>

INCHI for #<Metabolite:0x00007fed158ef0f8>

Structure for #<Metabolite:0x00007fed158ef0f8>

3D Structure for #<Metabolite:0x00007fed158ef0f8>