ChemFOnt: Showing chemical card for Homoserine (CFc000332908)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:30 UTC

Chemfont ID

CFc000332908

Molecule Identification

Common Name

Homoserine

Definition

Homoserine, 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 .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-4-hydroxybutanoic acid	ChEBI
DL-Homoserine	ChEBI
Hse	ChEBI
2-Amino-4-hydroxybutanoate	Generator
L Isomer OF homoserine	MeSH
Homoserine L-isomer	MeSH
L-Isomer OF homoserine	MeSH

Chemical Formula

C₄H₉NO₃

Average Molecular Weight

119.1192

Monoisotopic Molecular Weight

119.058243159

IUPAC Name

2-amino-4-hydroxybutanoic acid

Traditional Name

homoserine

CAS Registry Number

498-19-1

SMILES

NC(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)

InChI Key

UKAUYVFTDYCKQA-UHFFFAOYSA-N

Chemical Taxonomy

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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:30653 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0000719)

Food

Pulse

Pea

Common pea (FooDB: FOOD00141)

Herb and spice

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Process

Not Available

Role

Biological role

Anti sickling (HMDB: HMDB0000719)

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000521

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Homoserine

METLIN ID

Not Available

PubChem Compound

779

PDB ID

Not Available

ChEBI ID

30653

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Homoserine (CFc000332908)

MOL for CFc000332908 (Homoserine)

3D MOL for CFc000332908 (Homoserine)

3D SDF for CFc000332908 (Homoserine)

3D-SDF for CFc000332908 (Homoserine)

PDB for CFc000332908 (Homoserine)

3D PDB for CFc000332908 (Homoserine)

SMILES for CFc000332908 (Homoserine)

INCHI for CFc000332908 (Homoserine)

Structure for CFc000332908 (Homoserine)

3D Structure for CFc000332908 (Homoserine)