P. aeruginosa Metabolome Database: Selenohomocysteine (PAMDB001428)

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

PAMDB001428

Identification

Name:

Selenohomocysteine

Description:

Selenohomocysteine is the precursor of selenocysteine, which is synthesized by catalysis of cystathionine beta-synthase (EC 4.2.1.22) and cystathionine gamma-lyase (EC 4.4.1.1). Selenohomocysteine (lactone) has been found to be a competitive and irreversible inhibitor of lysyl oxidase. L-selenohomocysteine also can serve as a substituent donor in the beta-replacement reaction to yield selenocystathionine. (PMID: 10609891, 9405445, 6456763, 3338973)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Amino-4-selanyl-butanoate
2-Amino-4-selanyl-butanoic acid
Se-selenocysteine

Chemical Formula:

C₄H₉NO₂Se

Average Molecular Weight:

182.08

Monoisotopic Molecular Weight:

182.979850365

InChI Key:

RCWCGLALNCIQNM-UHFFFAOYSA-N

InChI:

InChI=1S/C4H9NO2Se/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)

CAS number:

29412-93-9

IUPAC Name:

2-amino-4-selanylbutanoic acid

Traditional IUPAC Name:

2-amino-4-selanylbutanoic acid

SMILES:

NC(CC[SeH])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
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Selenol
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:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	210.0 mg/mL	ALOGPS
logP	-3.1	ALOGPS
logP	-3.9	ChemAxon
logS	0.06	ALOGPS
pKa (Strongest Acidic)	1.41	ChemAxon
pKa (Strongest Basic)	9.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.16 m³·mol^-1	ChemAxon
Polarizability	12.78 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:

Selenocystathionine + Water <> Selenohomocysteine + Ammonia + Pyruvic 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	splash10-001r-1900000000-8c5ef30ac2fe25f165fe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0900000000-2b4556d8cf18b53be4d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-5900000000-2d48596c12bbf13ea974	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-17c55a96eff48db32ab4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01x9-6900000000-1285534df513770bbd95	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9400000000-fa4748f901bed9dc4482	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
Esaki N, Seraneeprakarn V, Tanaka H, Soda K: Purification and characterization of Clostridium sticklandii D-selenocystine alpha, beta-lyase. J Bacteriol. 1988 Feb;170(2):751-6. Pubmed: 3338973
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
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Liu G, Nellaiappan K, Kagan HM: Irreversible inhibition of lysyl oxidase by homocysteine thiolactone and its selenium and oxygen analogues. Implications for homocystinuria. J Biol Chem. 1997 Dec 19;272(51):32370-7. Pubmed: 9405445
Soda, K., Oikawa, T., Esaki, N. (1999). "Vitamin B6 enzymes participating in selenium amino acid metabolism." Biofactors 10:257-262. Pubmed: 10609891

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	HMDB04119
Pubchem Compound ID	6326973
Kegg ID	C05698
ChemSpider ID	389632
Wikipedia ID	Not Available
BioCyc ID	SELENOHOMOCYSTEINE
EcoCyc ID	SELENOHOMOCYSTEINE

Selenohomocysteine (PAMDB001428)

Structure for Selenohomocysteine (PAMDB001428)