| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:09:10 -0700 |
| HMDB ID |
HMDB00719 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
L-Homoserine |
| Description |
Homoserine is a more reactive variant of the amino acid serine. In this variant, the hydroxyl side chain contains an additional CH2 group which brings the hydroxyl group closer to its own carboxyl group, allowing it to chemically react to form a five-membered ring. This occurs at the point that amino acids normally join to their neighbours in a peptide bond. Homoserine is therefore unsuitable for forming proteins and has been eliminated from the repertoire of amino acids used by living things. Homoserine is the final product on the C-terminal end of the N-terminal fragment following a cyanogen bromide cleavage. (wikipedia). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| 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
|
| Chemical Formula |
C4H9NO3 |
| Average Molecular Weight |
119.1192 |
| Monoisotopic Molecular Weight |
119.058243159 |
| IUPAC Name |
(2S)-2-amino-4-hydroxybutanoic acid |
| Traditional IUPAC Name |
L-homoserine |
| CAS Registry Number |
672-15-1 |
| SMILES |
N[C@@H](CCO)C(O)=O |
| InChI Identifier |
InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1 |
| InChI Key |
UKAUYVFTDYCKQA-VKHMYHEASA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Amino Acids, Peptides, and Analogues |
| Class |
Amino Acids and Derivatives |
| Sub Class |
Alpha Amino Acids and Derivatives |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- alpha-amino acid(ChEBI)
|
| Substituents |
- 1,3 Aminoalcohol
- Carboxylic Acid
- Primary Alcohol
- Primary Aliphatic Amine (Alkylamine)
|
| Direct Parent |
Alpha Amino Acids and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Protein synthesis, amino acid biosynthesis
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| Application |
Not Available |
| Cellular locations |
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
203 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
1000.0 mg/mL |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
|
| Spectra |
|
| Gas-MS Spectrum |
| 13C NMR Spectrum |
| 1H NMR Spectrum |
| MS/MS Spectrum Quattro_QQQ 10 |
| MS/MS Spectrum Quattro_QQQ 25 |
| MS/MS Spectrum Quattro_QQQ 40 |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| [1H,1H] 2D NMR Spectrum |
| [1H,13C] 2D NMR Spectrum |
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| Biological Properties |
| Cellular Locations |
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| Biofluid Locations |
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| Tissue Location |
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| Pathways |
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| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
12.0 (11.3-17.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.29 +/- 0.37 umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
Not Available |
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
DB04193  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB000522 |
| KNApSAcK ID |
C00001366  |
| Chemspider ID |
12126  |
| KEGG Compound ID |
C00263  |
| BioCyc ID |
HOMO-SER  |
| BiGG ID |
34437  |
| Wikipedia Link |
Homoserine  |
| NuGOwiki Link |
HMDB00719  |
| Metagene Link |
HMDB00719  |
| METLIN ID |
5687  |
| PubChem Compound |
12647  |
| PDB ID |
HSE  |
| ChEBI ID |
15699  |
| References |
| 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. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Gazarian KG, Gening LV, Gazarian TG: L-Homoserine: a novel excreted metabolic marker of hepatitis B abnormally produced in liver from methionine. Med Hypotheses. 2002 Apr;58(4):279-83.
Pubmed: 12027520
- Compagnini A, Cunsolo V, Foti S, Saletti R: Improved accuracy in the matrix-assisted laser desorption/ionization-mass spectrometry determination of the molecular mass of cyanogen bromide fragments of proteins by post-cleavage reaction with tris(hydroxymethyl)aminomethane. Proteomics. 2001 Aug;1(8):967-74.
Pubmed: 11683513
- Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38.
Pubmed: 2026685
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.
Pubmed: 19212411
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