Bovine Metabolome Database: Showing metabocard for Selenomethionine (BMDB0003966)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:07:07 UTC

Update Date

2020-05-21 16:28:22 UTC

BMDB ID

BMDB0003966

Secondary Accession Numbers

BMDB03966

Metabolite Identification

Common Name

Selenomethionine

Description

Selenomethionine, also known as selenomethionine, 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). Selenomethionine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Selenomethionine exists in all living species, ranging from bacteria to humans. Selenomethionine can be converted into se-adenosylselenomethionine and phosphoric acid through its interaction with the enzyme S-adenosylmethionine synthase. In cattle, selenomethionine is involved in the metabolic pathway called the selenoamino acid metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Selenomethionine	ChEBI
Selenium methionine	ChEBI
Seleno-DL-methionine	ChEBI
(2S)-2-Amino-4-(methylseleno)butanoate	HMDB
(2S)-2-Amino-4-(methylseleno)butanoic acid	HMDB
(S)-2-Amino-4-(methylseleno)-butanoate	HMDB
(S)-2-Amino-4-(methylseleno)-butanoic acid	HMDB
(S)-2-Amino-4-(methylseleno)butanoate	HMDB
(S)-2-Amino-4-(methylseleno)butanoic acid	HMDB
(S)-2-Amino-4-(methylseleno)butyric acid	HMDB
2-Amino-4-(methylseleno)butanoate	HMDB
2-Amino-4-(methylseleno)butanoic acid	HMDB
2-Amino-4-(methylselenyl)butyrate	HMDB
2-Amino-4-(methylselenyl)butyric acid	HMDB
DL-Selenomethionine	HMDB
L(+)-Selenomethionine	HMDB
L-2-Amino-4-(methylselenyl)-butyric acid	HMDB
L-Selenomethionine	HMDB
L-Selenomethioninum	HMDB
MSE	HMDB
Selenium-L-methionine	HMDB
Seleno-D,L-methionine	HMDB
Seleno-L-methionine	HMDB
Selenomethionine se 75	HMDB
SeMet	HMDB
Sethotope	HMDB
Selenomethionine hydrochloride, (S)-isomer	HMDB
Selenomethionine, (S)-isomer	HMDB
Radioselenomethionine	HMDB
Selenomethionine, (+,-)-isomer	HMDB
Selenomethionine, (R)-isomer	HMDB
Se 75, selenomethionine	HMDB

Chemical Formula

C₅H₁₁NO₂Se

Average Molecular Weight

196.11

Monoisotopic Molecular Weight

196.995500429

IUPAC Name

2-amino-4-(methylselanyl)butanoic acid

Traditional Name

(+,-)-selenomethionine

CAS Registry Number

3211-76-5

SMILES

C[Se]CCC(N)C(O)=O

InChI Identifier

InChI=1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

InChI Key

RJFAYQIBOAGBLC-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
Selenoether
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organoselenium compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

selenoamino acid (CHEBI:27585 )
selenomethionines (CHEBI:27585 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	275 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.5	ALOGPS
logP	-3.3	ChemAxon
logS	-0.25	ALOGPS
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	9.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	42.91 m³·mol⁻¹	ChemAxon
Polarizability	14.92 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9300000000-ad31be05ded6d3690473	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9120000000-b81ef03513ebcd2db684	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0f89-0900000000-4949659ad5c41236a070	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9500000000-dbac3b4e6e034ebd3855	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9200000000-d58c983bc06091b8dd74	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0kai-2900000000-86628c3188ed75c0a1e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f6t-1900000000-185fb006e1bba095a984	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udj-1900000000-d4cebd865ad12ea7d7a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-8900000000-797a41add1f29f10c4dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-7900000000-60bc9ba77f492e1b35e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f95-5900000000-7b650680f083adef2064	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9200000000-027a3e15d6897c294431	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Fibroblasts
Kidney
Pancreas
Prostate Tissue

Pathways

Name	SMPDB/Pathwhiz	KEGG
Selenoamino Acid Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0003966

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012370

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

27585

References

Synthesis Reference

Jakubke, Hans D.; Fischer, J.; Jost, Karel; Rudinger, Josef. Amino acids and peptides. LXXXVI. Synthesis of L-selenomethionine, L-selenoethionine, and their tert-butoxy-carbonyl derivatives. Collection of Czechoslovak Chemical Communications (1968), 33(11), 3910-12.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. S-adenosylmethionine synthase isoform type-1

General function:: Coenzyme transport and metabolism
Specific function:: Catalyzes the formation of S-adenosylmethionine from methionine and ATP. The reaction comprises two steps that are both catalyzed by the same enzyme: formation of S-adenosylmethionine (AdoMet) and triphosphate, and subsequent hydrolysis of the triphosphate.
Gene Name:: MAT1A
Uniprot ID:: Q2KJC6
Molecular weight:: 43761.0

Reactions

Selenomethionine + Adenosine triphosphate + Water → Se-Adenosylselenomethionine + Hydrogen phosphate + Pyrophosphate	details

Enzyme Details

2. Methionine--tRNA ligase, cytoplasmic

General function:: Translation, ribosomal structure and biogenesis
Specific function:: Catalyzes the specific attachment of an amino acid to its cognate tRNA in a 2 step reaction: the amino acid (AA) is first activated by ATP to form AA-AMP and then transferred to the acceptor end of the tRNA. Plays a role in the synthesis of ribosomal RNA in the nucleolus.
Gene Name:: MARS1
Uniprot ID:: Q2T9L8
Molecular weight:: 100634.0

Reactions

Selenomethionine + Adenosine triphosphate + tRNA(Met) → Selenomethionyl-tRNA(Met) + Adenosine monophosphate + Pyrophosphate	details

Enzyme Details

3. Methionine adenosyltransferase 2 subunit beta

General function:: Not Available
Specific function:: Regulatory subunit of S-adenosylmethionine synthetase 2, an enzyme that catalyzes the formation of S-adenosylmethionine from methionine and ATP. Regulates MAT2A catalytic activity by changing its kinetic properties, increasing its affinity for L-methionine. Can bind NADP (in vitro).
Gene Name:: MAT2B
Uniprot ID:: Q29RI9
Molecular weight:: 37768.0

Reactions

Selenomethionine + Adenosine triphosphate + Water → Se-Adenosylselenomethionine + Hydrogen phosphate + Pyrophosphate	details

Showing metabocard for Selenomethionine (BMDB0003966)

Structure for BMDB0003966 (Selenomethionine)

Enzymes

Reactions

Reactions

Reactions