P. aeruginosa Metabolome Database: Selenocystathionine (PAMDB000666)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000666

Identification

Name:

Selenocystathionine

Description:

Selenocystathionine is formed from selenohomocysteine by the enzyme cystathionine beta-synthase (EC 4.2.1.22), as a by-product of cystathionine synthesis. It is an intermediate in selenoamine acid metabolism.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Amino-4-((2-amino-2-carboxyethyl)seleno)-Butanoate
2-Amino-4-((2-amino-2-carboxyethyl)seleno)-Butanoic acid
2-Amino-4-((2-amino-2-carboxyethyl)seleno)butanoate
2-Amino-4-((2-amino-2-carboxyethyl)seleno)butanoic acid
Selenate
Selenic acid
Selenocystathionine

Chemical Formula:

C₇H₁₄N₂O₄Se

Average Molecular Weight:

269.16

Monoisotopic Molecular Weight:

270.011878774

InChI Key:

ZNWYDQPOUQRDLY-UHFFFAOYSA-N

InChI:

InChI=1S/C7H14N2O4Se/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)

CAS number:

2196-58-9

IUPAC Name:

2-amino-4-[(2-amino-2-carboxyethyl)selanyl]butanoic acid

Traditional IUPAC Name:

selenocystathionine

SMILES:

NC(CC[Se]CC(N)C(O)=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound 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
Amino fatty acid
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Selenoether
Carboxylic acid
Hydrocarbon derivative
Primary amine
Organoselenium compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

Melting point:

58 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	86.8 mg/mL	ALOGPS
logP	-4	ALOGPS
logP	-7.4	ChemAxon
logS	-0.49	ALOGPS
pKa (Strongest Acidic)	1.2	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	56.89 m³·mol^-1	ChemAxon
Polarizability	21.05 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Menaquinol 8 + Selenocystathionine > Water + Menaquinone 8 + Selenite
Selenocystathionine + Water <> Selenohomocysteine + Ammonia + Pyruvic acid
O-Phosphorylhomoserine + Selenocysteine <> Selenocystathionine + Phosphate
O-Succinyl-L-homoserine + Selenocysteine <> Selenocystathionine + Succinic acid

Pathways:

Selenoamino acid metabolism pae00450

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00fr-2290000000-f2bec65ba3fa54257a2a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1490000000-c8e7ba1b974d80ad06fd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ba-4900000000-44733d945ca0a2123bdd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0910000000-949e30f57858894ebee4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uy0-5980000000-44fdd01e4d44e8a390bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9600000000-a128c15c6924127ebb1b	View in MoNA

References

References:

Esaki N, Nakamura T, Tanaka H, Suzuki T, Morino Y, Soda K: Enzymatic synthesis of selenocysteine in rat liver. Biochemistry. 1981 Jul 21;20(15):4492-6. Pubmed: 6456763
Freeman JL, Zhang LH, Marcus MA, Fakra S, McGrath SP, Pilon-Smits EA: Spatial imaging, speciation, and quantification of selenium in the hyperaccumulator plants Astragalus bisulcatus and Stanleya pinnata. Plant Physiol. 2006 Sep;142(1):124-34. Epub 2006 Aug 18. Pubmed: 16920881
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Neuhierl, B., Thanbichler, M., Lottspeich, F., Bock, A. (1999). "A family of S-methylmethionine-dependent thiol/selenol methyltransferases. Role in selenium tolerance and evolutionary relation." J Biol Chem 274:5407-5414. Pubmed: 10026151

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18170
HMDB ID	HMDB06343
Pubchem Compound ID	98223
Kegg ID	C05699
ChemSpider ID	88693
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

• Sulfate/thiosulfate import ATP-binding protein cysA

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex cysAWTP involved in sulfate/thiosulfate import. Responsible for energy coupling to the transport system
Gene Name:: cysA
Locus Tag:: PA0280
Molecular weight:: 36.8 kDa

Reactions

ATP + H(2)O + sulfate(Out) = ADP + phosphate + sulfate(In).

Protein Details

• Sulfate transport system permease protein cysW

General function:: Involved in transporter activity
Specific function:: Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: cysW
Locus Tag:: PA0281
Molecular weight:: 31.3 kDa

Protein Details

• Thiosulfate-binding protein

General function:: Involved in transporter activity
Specific function:: Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. This protein specifically binds thiosulfate and is involved in its transmembrane transport
Gene Name:: cysP
Locus Tag:: PA1493
Molecular weight:: 36.5 kDa

Transporters

Protein Details

• Sulfate/thiosulfate import ATP-binding protein cysA

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex cysAWTP involved in sulfate/thiosulfate import. Responsible for energy coupling to the transport system
Gene Name:: cysA
Locus Tag:: PA0280
Molecular weight:: 36.8 kDa

Reactions

ATP + H(2)O + sulfate(Out) = ADP + phosphate + sulfate(In).

Protein Details

• Sulfate transport system permease protein cysW

General function:: Involved in transporter activity
Specific function:: Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: cysW
Locus Tag:: PA0281
Molecular weight:: 31.3 kDa

Protein Details

• Thiosulfate-binding protein

General function:: Involved in transporter activity
Specific function:: Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. This protein specifically binds thiosulfate and is involved in its transmembrane transport
Gene Name:: cysP
Locus Tag:: PA1493
Molecular weight:: 36.5 kDa

Selenocystathionine (PAMDB000666)

Structure for Selenocystathionine (PAMDB000666)

Enzymes

Reactions

Transporters

Reactions