Human Metabolome Database Version 3.5

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Showing metabocard for L-Homoserine (HMDB00719)

Blood
Urine

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

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

Endogenous

Microbial

Biofunction

Protein synthesis, amino acid biosynthesis

Application

Not Available

Cellular locations

Extracellular

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

Predicted Properties

Property	Value	Source
Water Solubility	423 g/L	ALOGPS
LogP	-3.31	ALOGPS
LogP	-3.8	ChemAxon
LogS	0.55	ALOGPS
pKa (strongest acidic)	2.22	ChemAxon
pKa (strongest basic)	9.16	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 A²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.91	ChemAxon
Polarizability	11.44	ChemAxon
Formal Charge	0	ChemAxon
Physiological Charge	0	ChemAxon

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)

[1H,1H] 2D NMR Spectrum

[1H,13C] 2D NMR Spectrum

Biological Properties

Cellular Locations

Extracellular

Biofluid Locations

Blood
Urine

Tissue Location

Prostate

Pathways

Name	SMPDB Link	KEGG Link
Methionine Metabolism	SMP00033	map00270

Normal Concentrations

Biofluid	Status		Value	Age	Sex	Condition	Comments
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

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Homoserine Link_out

NuGOwiki Link

Metagene Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

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