Cannabis Compound Database: Showing Compound Card for Selenocysteine (CDB004952)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (17) Show 21 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:53:56 UTC

Updated at

2020-11-18 16:39:06 UTC

CannabisDB ID

CDB004952

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Selenocysteine

Description

Selenocysteine, also known as 3-seleno-alanine, 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. Selenocysteine is a very strong basic compound (based on its pKa). Selenocysteine exists in all living species, ranging from bacteria to humans. Within humans, selenocysteine participates in a number of enzymatic reactions. In particular, selenocysteine can be converted into L-alanine and hydrogen selenide; which is catalyzed by the enzyme selenocysteine lyase. In addition, selenocysteine and 2-ketobutyric acid can be biosynthesized from selenocystathionine through the action of the enzyme cystathionine gamma-lyase. In humans, selenocysteine is involved in selenoamino acid metabolism. The L-enantiomer of selenocysteine. Selenocysteine is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Selenyl-L-alanine	ChEBI
L-Selenocystein	ChEBI
L-Selenozystein	ChEBI
(2R)-2-Amino-3-selanylpropanoate	HMDB
(2R)-2-Amino-3-selanylpropanoic acid	HMDB
3-Seleno-alanine	HMDB
3-Selenoalanine	HMDB
L-Selenocysteine	HMDB

Chemical Formula

C₃H₇NO₂Se

Average Molecular Weight

168.05

Monoisotopic Molecular Weight

168.9642

IUPAC Name

(2R)-2-amino-3-selanylpropanoic acid

Traditional Name

L-selenocysteine

CAS Registry Number

3614-08-2

SMILES

N[C@@H](C[SeH])C(O)=O

InChI Identifier

InChI=1S/C3H7NO2Se/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1

InChI Key

ZKZBPNGNEQAJSX-REOHCLBHSA-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
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Selenol
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

proteinogenic amino acid (CHEBI:16633 )
L-alpha-amino acid (CHEBI:16633 )
L-alanine derivative (CHEBI:16633 )
selenocysteine (CHEBI:16633 )
Other amino acids (C05688 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Endocrine gland:

Thyroid gland

Cell and elements:

Cell:

Fibroblast

Subcellular:

Cytoplasm

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	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	-3.2	ALOGPS
logP	-4.1	ChemAxon
logS	0.29	ALOGPS
pKa (Strongest Acidic)	1.27	ChemAxon
pKa (Strongest Basic)	8.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	33.45 m³·mol⁻¹	ChemAxon
Polarizability	10.67 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

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Selenocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-5900000000-827b47dc191649f521ac	Spectrum
Predicted GC-MS	Selenocysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-5900000000-32e999fe6e3d67e322cb	Spectrum
Predicted GC-MS	Selenocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-0900000000-fadd5a69b2b225d034ac	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01b9-0900000000-8fe6412cebc1ca99fe59	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-5900000000-2408222e037ff9db752a	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-91ba91d891f89ff1fc23	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kk-6900000000-67c579b8ba30e155bcb3	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9200000000-0b58b77f13cec3df121d	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-59cfe0ab1984ab09d7af	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-7900000000-6f634fdb5ee7a8437ca7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1900000000-0f58b4784272be073705	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-0900000000-3a288e1fc4c42cfb333c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-0900000000-c29c42f6924485632ad3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2900000000-8f03b287aede9d710058	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Selenoamino Acid Metabolism

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Nucleoside diphosphate kinase A	NME1	17q21.3	P15531	details
Thioredoxin reductase 1, cytoplasmic	TXNRD1	12q23-q24.1	Q16881	details
Thioredoxin reductase 2, mitochondrial	TXNRD2	22q11.21	Q9NNW7	details
Cystathionine gamma-lyase	CTH	1p31.1	P32929	details
Selenide, water dikinase 2	SEPHS2	16p11.2	Q99611	details
Glutathione peroxidase 1	GPX1	3p21.3	P07203	details
Phospholipid hydroperoxide glutathione peroxidase, mitochondrial	GPX4	19p13.3	P36969	details
Glutathione peroxidase 3	GPX3	5q23	P22352	details
Glutathione peroxidase 2	GPX2	14q24.1	P18283	details
Type I iodothyronine deiodinase	DIO1	1p33-p32	P49895	details
Type II iodothyronine deiodinase	DIO2	14q24.2-q24.3	Q92813	details
Selenocysteine lyase	SCLY	2q37.3	Q96I15	details
Thioredoxin reductase 3	TXNRD3	3q21.3	Q86VQ6	details
Ethanolaminephosphotransferase 1	EPT1	2p23.3	Q9C0D9	details
O-phosphoseryl-tRNA(Sec) selenium transferase	SEPSECS	4p15.2	Q9HD40	details
Aflatoxin B1 aldehyde reductase member 4	AKR7L	1p36.13\|1p35-p36.1	Q8NHP1	details
Methionine-R-sulfoxide reductase B1	MSRB1	16p13.3	Q9NZV6	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Ethanolaminephosphotransferase 1	EPT1	2p23.3	Q9C0D9	details
Methionine-R-sulfoxide reductase B1	MSRB1	16p13.3	Q9NZV6	details

Receptors

Not Available

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cystathionine gamma-lyase	CTH	1p31.1	P32929	details
Glutathione peroxidase 3	GPX3	5q23	P22352	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0003288

DrugBank ID

DB02345

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16633

References

General References

Not Available

Only showing the first 10 proteins. There are 21 proteins in total.

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Enzymes

Enzyme Details

1. Nucleoside diphosphate kinase A

General function:: Involved in nucleoside diphosphate kinase activity
Specific function:: Major role in the synthesis of nucleoside triphosphates other than ATP. Possesses nucleoside-diphosphate kinase, serine/threonine-specific protein kinase, geranyl and farnesyl pyrophosphate kinase, histidine protein kinase and 3'-5' exonuclease activities. Involved in cell proliferation, differentiation and development, signal transduction, G protein-coupled receptor endocytosis, and gene expression. Required for neural development including neural patterning and cell fate determination.
Gene Name:: NME1
Uniprot ID:: P15531
Molecular weight:: 17148.635

Enzyme Details

2. Thioredoxin reductase 1, cytoplasmic

General function:: Involved in oxidoreductase activity
Specific function:: Isoform 1 may possess glutaredoxin activity as well as thioredoxin reductase activity and induces actin and tubulin polymerization, leading to formation of cell membrane protrusions. Isoform 4 enhances the transcriptional activity of estrogen receptors alpha and beta while isoform 5 enhances the transcriptional activity of the beta receptor only. Isoform 5 also mediates cell death induced by a combination of interferon-beta and retinoic acid.
Gene Name:: TXNRD1
Uniprot ID:: Q16881
Molecular weight:: 70905.58

Enzyme Details

3. Thioredoxin reductase 2, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Maintains thioredoxin in a reduced state. Implicated in the defenses against oxidative stress. May play a role in redox-regulated cell signaling.
Gene Name:: TXNRD2
Uniprot ID:: Q9NNW7
Molecular weight:: 56506.275

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

Enzyme Details

5. Selenide, water dikinase 2

General function:: Involved in catalytic activity
Specific function:: Synthesizes selenophosphate from selenide and ATP.
Gene Name:: SEPHS2
Uniprot ID:: Q99611
Molecular weight:: 47304.695

Enzyme Details

6. Glutathione peroxidase 1

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects the hemoglobin in erythrocytes from oxidative breakdown.
Gene Name:: GPX1
Uniprot ID:: P07203
Molecular weight:: 22087.94

Enzyme Details

7. Phospholipid hydroperoxide glutathione peroxidase, mitochondrial

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects cells against membrane lipid peroxidation and cell death. Required for normal sperm development and male fertility. Could play a major role in protecting mammals from the toxicity of ingested lipid hydroperoxides. Essential for embryonic development. Protects from radiation and oxidative damage (By similarity).
Gene Name:: GPX4
Uniprot ID:: P36969
Molecular weight:: 25046.57

Enzyme Details

8. Glutathione peroxidase 3

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione.
Gene Name:: GPX3
Uniprot ID:: P22352
Molecular weight:: 25552.185

Enzyme Details

9. Glutathione peroxidase 2

General function:: Involved in glutathione peroxidase activity
Specific function:: Could play a major role in protecting mammals from the toxicity of ingested organic hydroperoxides. Tert-butyl hydroperoxide, cumene hydroperoxide and linoleic acid hydroperoxide but not phosphatidycholine hydroperoxide, can act as acceptors.
Gene Name:: GPX2
Uniprot ID:: P18283
Molecular weight:: 21953.835

Enzyme Details

10. Type I iodothyronine deiodinase

General function:: Involved in thyroxine 5'-deiodinase activity
Specific function:: Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into T3 (3,5,3'-triiodothyronine) and of T3 into T2 (3,3'-diiodothyronine). Plays a role in providing a source of plasma T3 by deiodination of T4 in peripheral tissues such as liver and kidney.
Gene Name:: DIO1
Uniprot ID:: P49895
Molecular weight:: 28924.21

Only showing the first 10 proteins. There are 21 proteins in total.

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Showing Compound Card for Selenocysteine (CDB004952)

Structure for CDB004952 (Selenocysteine)

Enzymes