Record Information
Version1.0
Creation date2010-04-08 22:04:36 UTC
Update date2019-11-26 02:54:56 UTC
Primary IDFDB000522
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Homoserine
DescriptionPresent in germinating peas, Jack bean seeds (Canavalia ensiformis) and the seedlings of many leguminous plants 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); Homoserine is an intermediate in the biosynthesis of three essential amino acids: methionine, threonine (an isomer of homoserine), and isoleucine. It forms by two reductions of aspartic acid via the intermediacy of aspartate semialdehyde.; Homoserine is an ?-amino acid with the chemical formula HO2CCH(NH2)CH2CH2OH. L-Homoserine is not one of the common amino acids encoded by DNA. It differs from the proteinogenic amino acid serine by insertion of an additional methylene group. Homoserine, or its lactone form, is the product of a cyanogen bromide cleavage of a peptide by degradation of methionine. L-Homoserine is found in many foods, some of which are cornmint, star fruit, common wheat, and nance.
CAS Number672-15-1
Structure
Thumb
Synonyms
SynonymSource
2-Amino-4-hydroxybutanoic acidChEBI
DL-HomoserineChEBI
HseChEBI
2-Amino-4-hydroxybutanoateGenerator
L Isomer OF homoserineMeSH
Homoserine L-isomerMeSH
L-Isomer OF homoserineMeSH
(2S)-2-amino-4-HydroxybutanoateGenerator
(2S)-2-amino-4-hydroxybutanoic acidbiospider
(S)-2-amino-4-hydroxy-Butanoatebiospider
(S)-2-amino-4-hydroxy-Butanoic acidbiospider
(S)-2-Amino-4-hydroxybutanoatebiospider
(S)-2-Amino-4-hydroxybutanoic acidbiospider
(S)-2-Amino-4-hydroxybutyric acidbiospider
(s)-homoserinebiospider
2-amino-4-hydroxy-Butyratebiospider
2-amino-4-hydroxy-Butyric acidbiospider
2-amino-4-hydroxy-L-Butyratebiospider
2-amino-4-hydroxy-L-Butyric acidbiospider
2-Amino-4-hydroxybutanoic acid; L-formdb_source
2-Amino-4-hydroxybutyratebiospider
2-Amino-4-hydroxybutyric acidbiospider
Butanoic acid, 2-amino-4-hydroxy-, (S)-biospider
Butyric acid, 2-amino-4-hydroxy-, L-biospider
Butyric acid, 2-amino-4-hydroxy-, L- (8CI)biospider
Homoserinebiospider
Homoserine (van)biospider
HSEbiospider
L-homoserinebiospider
Predicted Properties
PropertyValueSource
Water Solubility423 g/LALOGPS
logP-3.3ALOGPS
logP-3.8ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)2.22ChemAxon
pKa (Strongest Basic)9.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.91 m³·mol⁻¹ChemAxon
Polarizability11.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H9NO3
IUPAC name2-amino-4-hydroxybutanoic acid
InChI IdentifierInChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)
InChI KeyUKAUYVFTDYCKQA-UHFFFAOYSA-N
Isomeric SMILESNC(CCO)C(O)=O
Average Molecular Weight119.1192
Monoisotopic Molecular Weight119.058243159
Classification
Description 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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • 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
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.33%; H 7.62%; N 11.76%; O 40.29%DFC
Melting PointMp 203° dec.DFC
Boiling PointNot Available
Experimental Water Solubility1000 mg/mL at 30 oCBEILSTEIN
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]26D -8.8 (c, 5 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f6x-1971000000-ef4042a88eff4a50f502JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9100000000-3c5ae1e5b01441b7feacJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-9800000000-9ea260791e719b48f9cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9100000000-d11642891f3de49e9998JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-5bf6035c5e41f69aab66JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-93b2c7b18eab445c1c73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4r-9600000000-428bc3d5a8b2d7e93598JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-587666a1822e64e2d08fJSpectraViewer
ChemSpider ID12126
ChEMBL IDCHEMBL11722
KEGG Compound IDC00263
Pubchem Compound ID12647
Pubchem Substance IDNot Available
ChEBI ID15699
Phenol-Explorer IDNot Available
DrugBank IDDB04193
HMDB IDHMDB00719
CRC / DFC (Dictionary of Food Compounds) IDBDF20-I:BDF22-K
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34437
KNApSAcK IDC00001366
HET IDHSE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHomoserine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Methionine MetabolismSMP00033 map00270
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.