U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C5H11NO2Se
Molecular Weight 196.11
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SELENOMETHIONINE

SMILES

C[Se]CC[C@H](N)C(O)=O

InChI

InChIKey=RJFAYQIBOAGBLC-BYPYZUCNSA-N
InChI=1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

HIDE SMILES / InChI

Molecular Formula C5H11NO2Se
Molecular Weight 196.11
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12656658 | https://examine.com/supplements/selenium

L-isomer of selenomethionine (Se-met) is a major natural food-form of selenium, synthetic L-Se-met or enriched food sources thereof such as selenium yeast are appropriate supplemental forms of Se for humans; for animals, DL-Se-met is acceptable. Ingested Se-met is either metabolized directly to reactive forms of selenium or stored in place of methionine in body proteins. Se-met metabolism is closely linked to protein turnover. Selenium, which is nutritionally essential for humans, is a constituent of more than two dozen selenoproteins that play critical roles in reproduction, thyroid hormone metabolism, DNA synthesis, and protection from oxidative damage and infection.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Selenium (selenomethionine)

Approved Use

Selenium (selenomethionine) is a natural antioxidant that delays the oxidation of polyunsaturated fatty acids and preserves the elasticity of tissue. Selenium is required for the production of certain prostaglandins, which promote healthy blood flow. In synergy with vitamin E, selenium promotes healthy growth and fertility, and improves the function of certain energy producing cells. Selenium also provides support for the immune system
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of selenomethionine supplementation in food on the excretion and toxicity of arsenic exposure in female mice.
2013-12
Effects of chronic dietary selenomethionine exposure on repeat swimming performance, aerobic metabolism and methionine catabolism in adult zebrafish (Danio rerio).
2013-04-15
Major differences among chemopreventive organoselenocompounds in the sustained elevation of cytoprotective genes.
2012-09
Induction of oxidative stress by selenomethionine in isolated hepatocytes of rainbow trout (Oncorhynchus mykiss).
2012-06
Attenuation of the cortisol response to stress in female rainbow trout chronically exposed to dietary selenomethionine.
2011-10
Chronic exposure to dietary selenomethionine increases gonadal steroidogenesis in female rainbow trout.
2011-10
Induction of ROS, p53, p21 in DEHP- and MEHP-exposed LNCaP cells-protection by selenium compounds.
2011-07
Low levels of selenium compounds are selectively toxic for a human neuron cell line through ROS/RNS increase and apoptotic process activation.
2011-03
Evaluation of cytotoxicity and oxidative DNA damaging effects of di(2-ethylhexyl)-phthalate (DEHP) and mono(2-ethylhexyl)-phthalate (MEHP) on MA-10 Leydig cells and protection by selenium.
2010-10-01
Inhibition of apoptotic signalling in spermine-treated vascular smooth muscle cells by a novel glutathione precursor.
2010-04-01
Regulation of cellular glutathione peroxidase by different forms and concentrations of selenium in primary cultured bovine hepatocytes.
2010-02
Selenomethionine stimulates expression of glutathione peroxidase 1 and 3 and growth of bovine mammary epithelial cells in primary culture.
2009-06
Characteristics of transport of selenoamino acids by epithelial amino acid transporters.
2009-02-12
Selenite reactivates silenced genes by modifying DNA methylation and histones in prostate cancer cells.
2008-11
Effects of naturally occurring and synthetic organoselenium compounds on protein profiling in androgen responsive and androgen independent human prostate cancer cells.
2008
Differential effects of naturally occurring and synthetic organoselenium compounds on biomarkers in androgen responsive and androgen independent human prostate carcinoma cells.
2007-04-01
Molecular mechanisms of the chemopreventive effect on hepatocellular carcinoma development in Mdr2 knockout mice.
2007-04
Seleno-L-methionine protects against beta-amyloid and iron/hydrogen peroxide-mediated neuron death.
2007-04
Selenomethionine induced transcriptional programs in human prostate cancer cells.
2007-02
Selenomethionine inhibits ultraviolet radiation-induced p53 transactivation.
2006-12
The crystal structure of iron-free human serum transferrin provides insight into inter-lobe communication and receptor binding.
2006-08-25
Selenium- or quercetin-induced retardation of DNA synthesis in primary prostate cells occurs in the presence of a concomitant reduction in androgen-receptor activity.
2006-07-28
Selenium long-term administration and its effect on mercury toxicity.
2006-06-14
Involvement of selenoprotein P in protection of human astrocytes from oxidative damage.
2006-05-01
Double-stranded RNA-dependent protein kinase (PKR) is a stress-responsive kinase that induces NFkappaB-mediated resistance against mercury cytotoxicity.
2006-03-13
Comparative effects of 2 antioxidants, selenomethionine and epigallocatechin-gallate, on catabolic and anabolic gene expression of articular chondrocytes.
2005-10
Selenium metabolites in human urine after ingestion of selenite, L-selenomethionine, or DL-selenomethionine: a quantitative case study by HPLC/ICPMS.
2005-09
Interaction of selenium compounds with zinc finger proteins involved in DNA repair.
2004-08
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.
2004-04-01
Selenium-containing compounds attenuate peroxynitrite-mediated NF-kappaB and AP-1 activation and interleukin-8 gene and protein expression in human leukocytes.
2003-11-01
In vitro evaluation of chemopreventive agents using cultured human prostate epithelial cells.
2003-10-10
Selenium and breast-feeding.
2002-11
Selenomethionine induction of DNA repair response in human fibroblasts.
2002-05-23
Micronutrients in cancer chemoprevention.
2002
[Determination of the selenomethionine content in grain and human blood].
1997-03
[Method of analysis of regional dynamics of the pancreas with 75Se-selenomethionine].
1977-04
75Se-selenomethionine excretion in bile and pancreatic juice.
1975
Count rate analysis as an adjunct to the 75Se-selenomethionine pancreas scan.
1969-10
Patents

Sample Use Guides

200 ug daily
Route of Administration: Oral
10 or 50 uM selenomethionine protects against cadmium toxicity in cultured K-562 cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:35:58 GMT 2025
Edited
by admin
on Mon Mar 31 18:35:58 GMT 2025
Record UNII
964MRK2PEL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
L-SELENOMETHIONINE
FCC  
Preferred Name English
SELENOMETHIONINE
HSDB   MART.   MI   WHO-DD  
Systematic Name English
NSC-760370
Code English
(S)-2-AMINO-4-(METHYLSELENO)BUTANOIC ACID
Systematic Name English
L-SELENOMETHIONINE [FCC]
Common Name English
BUTANOIC ACID, 2-AMINO-4-(METHYLSELENO)-, (S)-
Common Name English
SELENOMETHIONINE [USP-RS]
Common Name English
.ALPHA.-AMINO-.GAMMA.-(METHYLSELENO)BUTYRIC ACID
Systematic Name English
(2S)-2-AMINO-4-(METHYLSELENO)BUTANOIC ACID
Systematic Name English
SELENOMETHIONINE [MI]
Common Name English
BUTYRIC ACID, 2-AMINO-4-(METHYLSELENYL)-, L-
Common Name English
SELENOMETHIONINE, L-
Systematic Name English
SELENO-L-METHIONINE
Systematic Name English
SELENOMETHIONINE [MART.]
Common Name English
Selenomethionine [WHO-DD]
Common Name English
SELENOMETHIONINE [HSDB]
Common Name English
Classification Tree Code System Code
DSLD 2384 (Number of products:20)
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
DSLD 2033 (Number of products:7)
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
NCI_THESAURUS C275
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
EU-Orphan Drug EU/3/16/1782
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
Code System Code Type Description
WIKIPEDIA
SELENOMETHIONINE
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
CHEBI
62621
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
NCI_THESAURUS
C2833
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
ChEMBL
CHEMBL113178
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
MESH
D012645
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
EPA CompTox
DTXSID8046824
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
DAILYMED
964MRK2PEL
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
CHEBI
30021
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
DRUG CENTRAL
3544
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
DRUG BANK
DB11142
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
PUBCHEM
105024
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
RS_ITEM_NUM
1611955
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
FDA UNII
964MRK2PEL
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
CAS
3211-76-5
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
SMS_ID
100000128771
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
EVMPD
SUB36255
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
RXCUI
9644
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m9848
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY Merck Index
HSDB
3211-76-5
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
NSC
760370
Created by admin on Mon Mar 31 18:35:58 GMT 2025 , Edited by admin on Mon Mar 31 18:35:58 GMT 2025
PRIMARY
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LABELED -> NON-LABELED
Related Record Type Details
ACTIVE MOIETY