AFCDB: L-Homoserine (FDB000522)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:36 UTC

Update date

2019-11-26 02:54:56 UTC

Primary ID

FDB000522

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Homoserine

Description

Present 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 Number

672-15-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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

Chemical Formula

C4H9NO3

IUPAC name

2-amino-4-hydroxybutanoic acid

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

Isomeric SMILES

NC(CCO)C(O)=O

Average Molecular Weight

119.1192

Monoisotopic Molecular Weight

119.058243159

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).

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 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 40.33%; H 7.62%; N 11.76%; O 40.29%	DFC
Melting Point	Mp 203° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	1000 mg/mL at 30 oC	BEILSTEIN
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]26D -8.8 (c, 5 in H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Homoserine, 4 TMS, GC-MS Spectrum	splash10-0f6x-1971000000-ef4042a88eff4a50f502	Spectrum
Predicted GC-MS	Homoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9100000000-3c5ae1e5b01441b7feac	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-9800000000-9ea260791e719b48f9cd	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9100000000-d11642891f3de49e9998	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-5bf6035c5e41f69aab66	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-4900000000-93b2c7b18eab445c1c73	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0v4r-9600000000-428bc3d5a8b2d7e93598	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-587666a1822e64e2d08f	2015-05-27	View Spectrum