L-Homoserine (YMDB00104)

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Identification

YMDB ID

YMDB00104

Name

L-Homoserine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

L-Homoserine is an alpha-amino acid. L-Homoserine is derived from L-aspartate in the homoserine biosynthesis pathway. It is the precursor in homocysteine biosynthesis pathway and in threonine biosynthesis from homoserine pathway. In certain organisms, including the yeast Saccharomyces cerevisiae S288c and certain bacteria, hydrogen sulfide reacts with O-acetyl-L-homoserine, replacing the acetyl group and forming L-homocysteine. [Biocyc HOMOSERSYN-PWY and PWY-5344 and HOMOSER-THRESYN-PWY]

Structure

MOL SDF PDB SMILES InChI

Synonyms

(S)-2-amino-4-hydroxy-Butanoate
(S)-2-amino-4-hydroxy-Butanoic acid
(S)-2-Amino-4-hydroxybutanoate
(S)-2-Amino-4-hydroxybutanoic acid
(S)-Homoserine
2-amino-4-hydroxy-Butyrate
2-amino-4-hydroxy-Butyric acid
2-amino-4-hydroxy-L-Butyrate
2-amino-4-hydroxy-L-Butyric acid
2-Amino-4-hydroxybutanoate
2-Amino-4-hydroxybutanoic acid
2-Amino-4-hydroxybutyrate
2-Amino-4-hydroxybutyric acid
Homoserine
L-Homoserine
(2S)-2-Amino-4-hydroxybutanoic acid
(2S)-2-Amino-4-hydroxybutanoate
Homoserine L-isomer
L Isomer OF homoserine
L-Isomer OF homoserine

CAS number

672-15-1

Weight

Average: 119.1192
Monoisotopic: 119.058243159

InChI Key

UKAUYVFTDYCKQA-VKHMYHEASA-N

InChI

InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1

IUPAC Name

(2S)-2-amino-4-hydroxybutanoic acid

Traditional IUPAC Name

L-homoserine

Chemical Formula

C₄H₉NO₃

SMILES

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

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
Short-chain hydroxy acid
Fatty acid
1,3-aminoalcohol
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

homoserine (CHEBI:15699 )
Other amino acids (C00263 )

Physical Properties

State

Solid

Charge

Melting point

203 °C

Experimental Properties

Property	Value	Reference
Water Solubility	1000 mg/mL at 30 oC [BEILSTEIN]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	423 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-3.8	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	2.22	ChemAxon
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.91 m³·mol⁻¹	ChemAxon
Polarizability	11.44 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

Cysteine Metabolism	PW002383
Methionine metabolism and salvage	PW002384
Sulfur metabolism	PW002483
threonine metabolism	PW002401

KEGG Pathways

Cysteine and methionine metabolism	ec00270
Glycine, serine and threonine metabolism	ec00260
Lysine biosynthesis	ec00300
Sulfur metabolism	ec00920

SMPDB Reactions

L-Homoserine + Acetyl-CoA → Coenzyme A + Acetylhomoserine

NADPH + L-aspartic 4-semialdehyde + hydron → L-Homoserine + NADP

L-aspartic 4-semialdehyde + hydron + NADPH → NADP + L-Homoserine

L-Homoserine + Adenosine triphosphate → ADP + hydron + O-Phosphohomoserine

KEGG Reactions

NADH + L-aspartic 4-semialdehyde + hydron → NAD + L-Homoserine

L-aspartic 4-semialdehyde + NADPH + hydron → NADP + L-Homoserine

Adenosine triphosphate + L-Homoserine → hydron + O-Phosphohomoserine + ADP

Acetyl-CoA + L-Homoserine ↔ Coenzyme A + O-Acetyl-L-homoserine

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0v00-0930000000-3346aa2189b174721b86	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udj-1900000000-88ffce416068e87d5c9e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0gdi-1960000000-b676faeb6cb80ca15570	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0v00-0930000000-3346aa2189b174721b86	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udj-1900000000-88ffce416068e87d5c9e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gdi-1960000000-b676faeb6cb80ca15570	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gdi-0930000000-6216c27e0d6581b937aa	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udj-0900000000-d59a1b29c14ce935a8a2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ufv-0930000000-6efd3a5ade5c7320afb0	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9100000000-d741144429bbc0c89fb2	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0fk9-9530000000-9f3f4a1b429b17df7168	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9200000000-89f42491f91db334ecfc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-d1859b3d67ed95698fa3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0abc-9100000000-eb77443ca02c8ccbe33a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-395a3c4889481d35a3f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9300000000-634c194ce44ff0b3755f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-9300000000-0c6e3c4dd011ef8c64fd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-d6e4f803999f61b58a6e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-45ed6aea7015ba6e6ca5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9400000000-30b57c9aabcc05806ce4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0fk9-9400000000-74b23d9b0819343ff386	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-cde89cc67f5c874ed39c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-02t9-0891200000-72078b7028ff67e8adac	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-9000000000-178d6a086fe4d5123d31	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00kf-0900000000-1281df962d8640156255	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-02t9-0390000000-0afae0c03453d26542e6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-0891100000-48060b947316dc631321	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-9000000000-3427ff1b0434696ae956	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-0900000000-fd0f3bbc1a17c20a2475	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03xr-0390000000-5a4fde017ce3426e8cd5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-5900000000-a5903a71e92a78624d03	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-9100000000-422851033dffe854f591	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0ab9-9000000000-cd7b70e1ead33d38a19f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4l-9000000000-481d61466b1d0af71cc2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-9200000000-afddddfff24e50b7f835	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0gb9-1900000000-89eb5226702ae527a2be	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H 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
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
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D 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
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
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
Wiebers, J. L., Garner, H. R. (1967). "Acyl derivatives of homoserine as substrates for homocysteine synthesis in Neurospora crassa, yeast, and Escherichia coli." J Biol Chem 242:5644-5649.12325384
Robichon-Szulmajster, H., Cherest, H. (1967). "Regulation of homoserine O-transacetylase, first step in methionine biosyntheis in Saccharomyces cerevisiae." Biochem Biophys Res Commun 28:256-262.6035500
Cherest, H., Eichler, F., Robichon-Szulmajster, H. (1969). "Genetic and regulatory aspects of methionine biosynthesis in Saccharomyces cerevisiae." J Bacteriol 97:328-336.5764336
Huo, X., Viola, R. E. (1996). "Substrate specificity and identification of functional groups of homoserine kinase from Escherichia coli." Biochemistry 35:16180-16185.8973190
Kosuge, T., Gao, D., Hoshino, T. (2000). "Analysis of the methionine biosynthetic pathway in the extremely thermophilic eubacterium Thermus thermophilus." J Biosci Bioeng 90:271-279.16232856
Thomas, D., Barbey, R., Surdin-Kerjan, Y. (1993). "Evolutionary relationships between yeast and bacterial homoserine dehydrogenases." FEBS Lett 323:289-293.8500624
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Kokusenya, Yoshio; Matsuoka, Manabu. Synthesis of amino acids by electrochemical reduction. I. Synthesis of L-homoserine by electrochemical reduction of L-asparagine. Denki Kagaku oyobi Kogyo Butsuri Kagaku (1987), 55(2), 174-5.

External Links:

Resource	Link
CHEBI ID	15699
HMDB ID	HMDB00719
Pubchem Compound ID	12647
Kegg ID	C00263
ChemSpider ID	12126
FOODB ID	FDB006683
Wikipedia	Homoserine
BioCyc ID	HOMO-SER

Enzymes

Protein Details

1. Homoserine O-acetyltransferase

General function:: Involved in O-acetyltransferase activity
Specific function:: Acetyl-CoA + L-homoserine = CoA + O-acetyl-L- homoserine
Gene Name:: MET2
Uniprot ID:: P08465
Molecular weight:: 53659.0

Reactions

Acetyl-CoA + L-homoserine → CoA + O-acetyl-L-homoserine.

Protein Details

2. Homoserine kinase

General function:: Involved in ATP binding
Specific function:: Catalyzes the ATP-dependent phosphorylation of L- homoserine to L-homoserine phosphate
Gene Name:: THR1
Uniprot ID:: P17423
Molecular weight:: 38712.0

Reactions

ATP + L-homoserine → ADP + O-phospho-L-homoserine.

Protein Details

3. Aspartokinase

General function:: Involved in amino acid binding
Specific function:: ATP + L-aspartate = ADP + 4-phospho-L- aspartate
Gene Name:: HOM3
Uniprot ID:: P10869
Molecular weight:: 58109.19922

Reactions

ATP + L-aspartate → ADP + 4-phospho-L-aspartate.

Protein Details

4. Homoserine dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: L-homoserine + NAD(P)(+) = L-aspartate 4- semialdehyde + NAD(P)H
Gene Name:: HOM6
Uniprot ID:: P31116
Molecular weight:: 38501.69922

Reactions

L-homoserine + NAD(P)(+) → L-aspartate 4-semialdehyde + NAD(P)H.

Structure for #<Compound:0xaed66bf0>

Enzymes

Reactions

Reactions

Reactions

Reactions