O-Succinyl-L-homoserine (YMDB00917)

Identification

YMDB ID

YMDB00917

Name

O-Succinyl-L-homoserine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

O-succinyl-L-homoserine 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. O-succinyl-L-homoserine is a very strong basic compound (based on its pKa). selenocystathionine and O-succinyl-L-homoserine can be converted into selenocysteine and succinic acid; which is mediated by the enzyme cystathionine gamma-synthase. In yeast, O-succinyl-L-homoserine is involved in the metabolic pathway called the selenocompound metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

O-succinyl-L-homoserine
O-Succinylhomoserine
O4-Succinyl-L-homoserine
O-Succinylhomoserine, (DL)-isomer

CAS number

1492-23-5

Weight

Average: 219.1919
Monoisotopic: 219.074287153

InChI Key

GNISQJGXJIDKDJ-YFKPBYRVSA-N

InChI

InChI=1S/C8H13NO6/c9-5(8(13)14)3-4-15-7(12)2-1-6(10)11/h5H,1-4,9H2,(H,10,11)(H,13,14)/t5-/m0/s1

IUPAC Name

(2S)-2-amino-4-[(3-carboxypropanoyl)oxy]butanoic acid

Traditional IUPAC Name

O-succinyl-L-homoserine

Chemical Formula

C₈H₁₃NO₆

SMILES

N[C@@H](CCOC(=O)CCC(O)=O)C(O)=O

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
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Amino acid
Carboxylic acid
Amine
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

o-succinylhomoserine (CHEBI:16160 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	8.69 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-3.6	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.69	ChemAxon
pKa (Strongest Basic)	9.46	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	126.92 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	46.95 m³·mol⁻¹	ChemAxon
Polarizability	20.51 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

Organoleptic Properties

Not Available

SMPDB Pathways

Selenocompound metabolism	PW002472
Sulfur metabolism	PW002483

KEGG Pathways

Cysteine and methionine metabolism	ec00270
Selenocompound metabolism	ec00450
Sulfur metabolism	ec00920

SMPDB Reactions

Selenocystathionine + O-Succinyl-L-homoserine ↔ Selenocysteine + Succinic acid

KEGG Reactions

O-Succinyl-L-homoserine + water ↔ hydron + Ammonium + 2-Ketobutyric acid + Succinic acid

O-Succinyl-L-homoserine + L-Cysteine → L-Cystathionine + hydron + Succinic acid

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-9600000000-0ee701fa496e19e3d173	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-1950000000-5b18c68cf76a73eb1d8f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pi0-7900000000-3331dd355814be8ede11	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9400000000-146c8b009d4e75570320	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014j-7690000000-0163fcb4afd466414db2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-9720000000-dd9470ad7562bdf591b1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05tb-9200000000-ae21c8bfb909ac97af60	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Ono, B., Ishii, N., Naito, K., Miyoshi, S., Shinoda, S., Yamamoto, S., Ohmori, S. (1993). "Cystathionine gamma-lyase of Saccharomyces cerevisiae: structural gene and cystathionine gamma-synthase activity." Yeast 9:389-397.8511969

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16160
HMDB ID	Not Available
Pubchem Compound ID	439406
Kegg ID	C01118
ChemSpider ID	388523
FOODB ID	FDB031067
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Putative cystathionine gamma-synthase YML082W

General function:: Involved in pyridoxal phosphate binding
Specific function:: O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:: Not Available
Uniprot ID:: Q04533
Molecular weight:: 74312.70313

Reactions

O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.

Protein Details

2. Putative cystathionine gamma-synthase YLL058W

General function:: Involved in pyridoxal phosphate binding
Specific function:: O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:: Not Available
Uniprot ID:: Q12198
Molecular weight:: 64222.80078

Reactions

O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.

Protein Details

3. Cystathionine gamma-synthase

General function:: Involved in pyridoxal phosphate binding
Specific function:: O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:: STR2
Uniprot ID:: P47164
Molecular weight:: 72349.89844

Reactions

O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.

Structure for #<Compound:0xa3590d3c>

Enzymes

Reactions

Reactions

Reactions