Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 08:10:37 UTC

Update Date

2023-02-21 17:16:51 UTC

HMDB ID

HMDB0003966

Secondary Accession Numbers

HMDB03966

Metabolite Identification

Common Name

Selenomethionine

Description

Selenomethionine (CAS: 1464-42-2) is an amino acid containing selenium that cannot be synthesized by higher animals but can be obtained from plant material. Selenomethionine is the major seleno-compound in cereal grains (wheat grain, maize, and rice), soybeans, and enriched yeast. Seleno-compounds present in plants may have a profound effect on the health of animals and human subjects. It is now known that the total Se content cannot be used as an indication of its efficacy, but knowledge of individual selenocompounds is necessary to fully assess the significance. Thus, speciation of the seleno-compounds has moved to the forefront. Since animals and man are dependent upon plants for their nutritional requirements, this makes the types of seleno-compounds in plants even more critical. Se enters the food chain through incorporation into plant proteins, mostly as selenocysteine and selenomethionine at normal Se levels. There are two possible pathways for the catabolism of selenomethionine. One is the transsulfuration pathway via selenocystathionine to produce selenocysteine, which in turn is degraded into H2Se by the enzyme beta-lyase. The other pathway is the transamination-decarboxylation pathway. It was estimated that 90% of methionine is metabolized through this pathway and thus could be also the major route for selenomethionine catabolism (PMID:14748935 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Selenomethionine, (+,-)-isomer	HMDB
Selenomethionine se 75	HMDB
Radioselenomethionine	HMDB
Selenomethionine, (S)-isomer	HMDB
Sethotope	HMDB
Se 75, selenomethionine	HMDB
Selenomethionine hydrochloride, (S)-isomer	HMDB
(2S)-2-Amino-4-(methylseleno)butanoic acid	HMDB
(2S)-2-Azaniumyl-4-methylselanylbutanoate	HMDB
L-Selenomethionine	HMDB
Seleno-L-methionine	HMDB
2-Amino-4-(methylseleno)butanoic acid	HMDB
2-Amino-4-(methylseleno)butyric acid	HMDB
2-Amino-4-(methylselenyl)butyric acid	HMDB
Selenium methionine	HMDB
Selenomethionine	MeSH

Chemical Formula

C₅H₁₁NO₂Se

Average Molecular Weight

196.11

Monoisotopic Molecular Weight

196.995500429

IUPAC Name

(2S)-2-amino-4-(methylselanyl)butanoic acid

Traditional Name

L-selenomethionine

CAS Registry Number

3211-76-5

SMILES

C[Se]CC[C@H](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)/t4-/m0/s1

InChI Key

RJFAYQIBOAGBLC-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

amino acid zwitterion (CHEBI:62621 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	109 g/L	ALOGPS
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	14.64 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	131.516	30932474
DeepCCS	[M-H]-	127.76	30932474
DeepCCS	[M-2H]-	165.149	30932474
DeepCCS	[M+Na]+	140.342	30932474
AllCCS	[M+H]+	139.6	32859911
AllCCS	[M+H-H2O]+	136.0	32859911
AllCCS	[M+NH4]+	143.0	32859911
AllCCS	[M+Na]+	144.0	32859911
AllCCS	[M-H]-	144.5	32859911
AllCCS	[M+Na-2H]-	147.3	32859911
AllCCS	[M+HCOO]-	150.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	397.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	442.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	283.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	57.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	48.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	282.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	229.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	815.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	554.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	38.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	610.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	764.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	550.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	393.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Selenomethionine	C[Se]CC[C@H](N)C(O)=O	2007.2	Standard polar	33892256
Selenomethionine	C[Se]CC[C@H](N)C(O)=O	1392.4	Standard non polar	33892256
Selenomethionine	C[Se]CC[C@H](N)C(O)=O	2026.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Selenomethionine,1TMS,isomer #1	C[Se]CC[C@H](N)C(=O)O[Si](C)(C)C	1467.1	Semi standard non polar	33892256
Selenomethionine,1TMS,isomer #2	C[Se]CC[C@H](N[Si](C)(C)C)C(=O)O	1524.4	Semi standard non polar	33892256
Selenomethionine,2TMS,isomer #1	C[Se]CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1560.2	Semi standard non polar	33892256
Selenomethionine,2TMS,isomer #1	C[Se]CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1433.4	Standard non polar	33892256
Selenomethionine,2TMS,isomer #1	C[Se]CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1511.8	Standard polar	33892256
Selenomethionine,2TMS,isomer #2	C[Se]CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1685.7	Semi standard non polar	33892256
Selenomethionine,2TMS,isomer #2	C[Se]CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1475.7	Standard non polar	33892256
Selenomethionine,2TMS,isomer #2	C[Se]CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1675.7	Standard polar	33892256
Selenomethionine,3TMS,isomer #1	C[Se]CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1738.9	Semi standard non polar	33892256
Selenomethionine,3TMS,isomer #1	C[Se]CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1556.1	Standard non polar	33892256
Selenomethionine,3TMS,isomer #1	C[Se]CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1484.3	Standard polar	33892256
Selenomethionine,1TBDMS,isomer #1	C[Se]CC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1708.2	Semi standard non polar	33892256
Selenomethionine,1TBDMS,isomer #2	C[Se]CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	1768.3	Semi standard non polar	33892256
Selenomethionine,2TBDMS,isomer #1	C[Se]CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2030.0	Semi standard non polar	33892256
Selenomethionine,2TBDMS,isomer #1	C[Se]CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1841.5	Standard non polar	33892256
Selenomethionine,2TBDMS,isomer #1	C[Se]CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1788.1	Standard polar	33892256
Selenomethionine,2TBDMS,isomer #2	C[Se]CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2129.0	Semi standard non polar	33892256
Selenomethionine,2TBDMS,isomer #2	C[Se]CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1898.5	Standard non polar	33892256
Selenomethionine,2TBDMS,isomer #2	C[Se]CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1865.7	Standard polar	33892256
Selenomethionine,3TBDMS,isomer #1	C[Se]CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2403.2	Semi standard non polar	33892256
Selenomethionine,3TBDMS,isomer #1	C[Se]CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2150.5	Standard non polar	33892256
Selenomethionine,3TBDMS,isomer #1	C[Se]CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1897.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Selenomethionine GC-MS (1 TMS)	splash10-0pc0-2910000000-c7140386a1899064bb79	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Selenomethionine GC-MS (2 TMS)	splash10-00b9-0950000000-05c9f3aa6ccd78087856	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Selenomethionine 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 - Selenomethionine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0f89-0900000000-4949659ad5c41236a070	2020-03-10	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-9500000000-dbac3b4e6e034ebd3855	2020-03-10	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4i-9200000000-d58c983bc06091b8dd74	2020-03-10	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine , positive-QTOF	splash10-0kai-2900000000-86628c3188ed75c0a1e6	2020-03-10	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine 35V, Negative-QTOF	splash10-0006-9000000000-177c9b324903fd3e8d24	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine 10V, Positive-QTOF	splash10-0kai-2900000000-c78bec4d8caa8d16c051	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine 20V, Positive-QTOF	splash10-0a4i-9700000000-20cf34caac47550586a1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine 40V, Positive-QTOF	splash10-0a4i-9500000000-76fe5651b983cac7009a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine 10V, Positive-QTOF	splash10-0kai-2900000000-4a553db248ff377f5b2d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine 20V, Positive-QTOF	splash10-0a4i-9600000000-8cd75528c9e54bd6d31a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine 40V, Positive-QTOF	splash10-0a4i-9100000000-94daf4b2f125f3a08fc7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Selenomethionine 35V, Positive-QTOF	splash10-0kai-2900000000-821aeeb1835bf094beb8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 10V, Positive-QTOF	splash10-0f6t-1900000000-4c7499267ca09c35d1fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 20V, Positive-QTOF	splash10-0udj-1900000000-c8febb206f8338bc0103	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 40V, Positive-QTOF	splash10-00di-8900000000-ed5cee25f7460f6dee63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 10V, Negative-QTOF	splash10-0007-7900000000-d4ba86036408b6707652	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 20V, Negative-QTOF	splash10-0f6w-5900000000-98925ed00d83d0cb75d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 40V, Negative-QTOF	splash10-006x-9200000000-a9e17e100c4c54504073	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 10V, Positive-QTOF	splash10-0uea-0900000000-f1f33c2d1c43e09835ec	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 20V, Positive-QTOF	splash10-0a4i-5900000000-c0032d5daf3b2b7fe72a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 40V, Positive-QTOF	splash10-0a4i-5900000000-92d483635221139105e7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 10V, Negative-QTOF	splash10-0006-9000000000-f9689d19a8a4fb34dc2c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 20V, Negative-QTOF	splash10-0006-9000000000-f9689d19a8a4fb34dc2c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Selenomethionine 40V, Negative-QTOF	splash10-0006-9000000000-f9689d19a8a4fb34dc2c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2020-03-10	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Fibroblasts
Kidney
Pancreas
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Selenocompound metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.69 (0.56 - 0.82) uM	Adult (>18 years old)	Not Specified	Normal	15786488	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0 - 0.002 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	16132136	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.303 +/- 0.099 uM	Adult (>18 years old)	Not Specified	Prostate cancer	15041072	details

Associated Disorders and Diseases

Disease References

Prostate cancer
Nyman DW, Suzanne Stratton M, Kopplin MJ, Dalkin BL, Nagle RB, Jay Gandolfi A: Selenium and selenomethionine levels in prostate cancer patients. Cancer Detect Prev. 2004;28(1):8-16. [PubMed:15041072 ]

Associated OMIM IDs

176807 (Prostate cancer)

External Links

DrugBank ID

DB11142

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012156

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05335

BioCyc ID

SELENOMETHIONINE

BiGG ID

Not Available

Wikipedia Link

Selenomethionine

METLIN ID

Not Available

PubChem Compound

105024

PDB ID

Not Available

ChEBI ID

30021

Food Biomarker Ontology

Not Available

VMH ID

SELMETH

MarkerDB ID

MDB00000436

Good Scents ID

Not Available

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)

Download (PDF)

General References

Greenwald P, Milner JA, Anderson DE, McDonald SS: Micronutrients in cancer chemoprevention. Cancer Metastasis Rev. 2002;21(3-4):217-30. [PubMed:12549762 ]
Pointner H, Kinast H, Flegel U: 75Se-selenomethionine excretion in bile and pancreatic juice. Digestion. 1975;12(1):61-4. [PubMed:1175867 ]
Seo YR, Sweeney C, Smith ML: Selenomethionine induction of DNA repair response in human fibroblasts. Oncogene. 2002 May 23;21(23):3663-9. [PubMed:12032834 ]
Yang X, Tian Y, Ha P, Gu L: [Determination of the selenomethionine content in grain and human blood]. Wei Sheng Yan Jiu. 1997 Mar;26(2):113-6. [PubMed:10325615 ]
Hoang TT, Chen Y, May SW, Browner RF: Analysis of organoselenium compounds in human urine using active carbon and chemically modified silica sol-gel surface-assisted laser desorption/ionization high-resolution time-of-flight mass spectrometry. Anal Chem. 2004 Apr 1;76(7):2062-70. [PubMed:15053672 ]
Dorea JG: Selenium and breast-feeding. Br J Nutr. 2002 Nov;88(5):443-61. [PubMed:12425725 ]
Wally J, Halbrooks PJ, Vonrhein C, Rould MA, Everse SJ, Mason AB, Buchanan SK: The crystal structure of iron-free human serum transferrin provides insight into inter-lobe communication and receptor binding. J Biol Chem. 2006 Aug 25;281(34):24934-44. Epub 2006 Jun 22. [PubMed:16793765 ]
Cabanero AI, Madrid Y, Camara C: Selenium long-term administration and its effect on mercury toxicity. J Agric Food Chem. 2006 Jun 14;54(12):4461-8. [PubMed:16756381 ]
Wan XS, Zhou Z, Kennedy AR, Kopelovich L: In vitro evaluation of chemopreventive agents using cultured human prostate epithelial cells. Oncol Rep. 2003 Nov-Dec;10(6):2009-14. [PubMed:14534735 ]
Nakanishi F, Kasuga T, Kobayashi T, Miyabayashi H, Yano K: [Method of analysis of regional dynamics of the pancreas with 75Se-selenomethionine]. Kaku Igaku. 1977 Apr;14(2):223-32. [PubMed:559835 ]
Agnew JE, McCarthy DM, Melmed RNBOUCHIER IA: Count rate analysis as an adjunct to the 75Se-selenomethionine pancreas scan. Br J Radiol. 1969 Oct;42(502):762-9. [PubMed:5345341 ]
Kuehnelt D, Kienzl N, Traar P, Le NH, Francesconi KA, Ochi T: Selenium metabolites in human urine after ingestion of selenite, L-selenomethionine, or DL-selenomethionine: a quantitative case study by HPLC/ICPMS. Anal Bioanal Chem. 2005 Sep;383(2):235-46. Epub 2005 Oct 12. [PubMed:16132136 ]
Whanger PD: Selenium and its relationship to cancer: an update. Br J Nutr. 2004 Jan;91(1):11-28. [PubMed:14748935 ]

Enzymes

Enzyme Details

1. Methionine synthase

General function:: Involved in cobalamin binding
Specific function:: Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:: MTR
Uniprot ID:: Q99707
Molecular weight:: 140525.91

Reactions

Selenohomocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid → Selenomethionine + Tetrahydropteroyltri-L-glutamic acid	details

Enzyme Details

2. S-adenosylmethionine synthase isoform type-2

General function:: Involved in methionine adenosyltransferase activity
Specific function:: Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name:: MAT2A
Uniprot ID:: P31153
Molecular weight:: 43660.37

Reactions

Adenosine triphosphate + Selenomethionine + Water → Phosphate + Pyrophosphate + Se-Adenosylselenomethionine	details

Enzyme Details

3. S-adenosylmethionine synthase isoform type-1

General function:: Involved in methionine adenosyltransferase activity
Specific function:: Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name:: MAT1A
Uniprot ID:: Q00266
Molecular weight:: 43647.6

Reactions

Adenosine triphosphate + Selenomethionine + Water → Phosphate + Pyrophosphate + Se-Adenosylselenomethionine	details

Enzyme Details

4. Cystathionine gamma-lyase

General function:: Involved in pyridoxal phosphate binding
Specific function:: Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:: CTH
Uniprot ID:: P32929
Molecular weight:: 41259.91

Reactions

Selenomethionine + Water → Methaneselenol + Ammonia + 2-Ketobutyric acid	details

Enzyme Details

5. Methionine--tRNA ligase, cytoplasmic

General function:: Involved in nucleotide binding
Specific function:: Not Available
Gene Name:: MARS
Uniprot ID:: P56192
Molecular weight:: 101114.925

Reactions

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

Enzyme Details

6. Methionine adenosyltransferase 2 subunit beta

General function:: Involved in dTDP-4-dehydrorhamnose reductase activity
Specific function:: Non-catalytic regulatory subunit of S-adenosylmethionine synthetase 2 (MAT2A), an enzyme that catalyzes the formation of S-adenosylmethionine from methionine and ATP. Regulates the activity of S-adenosylmethionine synthetase 2 by changing its kinetic properties, rendering the enzyme more susceptible to S-adenosylmethionine inhibition.
Gene Name:: MAT2B
Uniprot ID:: Q9NZL9
Molecular weight:: Not Available

Reactions

Adenosine triphosphate + Selenomethionine + Water → Phosphate + Pyrophosphate + Se-Adenosylselenomethionine	details

Enzyme Details

7. Methionine--tRNA ligase, mitochondrial

General function:: Involved in nucleotide binding
Specific function:: Not Available
Gene Name:: MARS2
Uniprot ID:: Q96GW9
Molecular weight:: 66590.29

Reactions

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

Showing metabocard for Selenomethionine (HMDB0003966)

MOL for HMDB0003966 (Selenomethionine)

3D MOL for HMDB0003966 (Selenomethionine)

3D SDF for HMDB0003966 (Selenomethionine)

3D-SDF for HMDB0003966 (Selenomethionine)

PDB for HMDB0003966 (Selenomethionine)

3D PDB for HMDB0003966 (Selenomethionine)

SMILES for HMDB0003966 (Selenomethionine)

INCHI for HMDB0003966 (Selenomethionine)

Structure for HMDB0003966 (Selenomethionine)

3D Structure for HMDB0003966 (Selenomethionine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions