Record Information
Version1.0
Creation date2010-04-08 22:04:36 UTC
Update date2018-05-28 23:02:02 UTC
Primary IDFDB000521
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHomoserine
DescriptionHomoserine, also known as L-isomer of homoserine or 2-amino-4-hydroxybutanoic acid, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Homoserine is soluble (in water) and a moderately acidic compound (based on its pKa). Homoserine can be found in common pea and ginkgo nuts, which makes homoserine a potential biomarker for the consumption of these food products. Homoserine (also called isothreonine) is an α-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 -CH2- unit into the backbone. Homoserine, or its lactone form, is the product of a cyanogen bromide cleavage of a peptide by degradation of methionine .
CAS Number498-19-1
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-Amino-4-hydroxybutanoic acidChEBI
2-Amino-4-hydroxybutanoic acidChEBI
2-Amino-4-hydroxybutyric acidChEBI
HomoserineChEBI
(2S)-2-Amino-4-hydroxybutanoateGenerator
2-Amino-4-hydroxybutanoateGenerator
2-Amino-4-hydroxybutyrateGenerator
(S)-2-Amino-4-hydroxy-butanoateHMDB
(S)-2-Amino-4-hydroxy-butanoic acidHMDB
(S)-2-Amino-4-hydroxybutanoateHMDB
(S)-2-Amino-4-hydroxybutanoic acidHMDB
(S)-HomoserineHMDB
2-Amino-4-hydroxy-butyrateHMDB
2-Amino-4-hydroxy-butyric acidHMDB
2-Amino-4-hydroxy-L-butyrateHMDB
2-Amino-4-hydroxy-L-butyric acidHMDB
Homoserine L-isomerHMDB
L Isomer OF homoserineHMDB
L-Isomer OF homoserineHMDB
Homoserine, 9CIdb_source
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H9NO3
IUPAC name(2S)-2-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 l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 40.33%; H 7.62%; N 11.76%; O 40.29%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f6x-1971000000-ef4042a88eff4a50f502View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9100000000-3c5ae1e5b01441b7feacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-9800000000-9ea260791e719b48f9cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9100000000-d11642891f3de49e9998View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-5bf6035c5e41f69aab66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-93b2c7b18eab445c1c73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4r-9600000000-428bc3d5a8b2d7e93598View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-587666a1822e64e2d08fView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBDF20-I:BDF20-I
EAFUS IDNot Available
Dr. Duke IDHOMOSERINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti sicklingDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).