L-homoserine (CHEBI:15699)

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ChEBI Name	L-homoserine

ChEBI ID	CHEBI:15699

ChEBI ASCII Name	L-homoserine

Definition	The L-enantiomer of homoserine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:43131, CHEBI:6246, CHEBI:13123, CHEBI:21330

Supplier Information	ZINC000008551087

Download	Molfile XML SDF

Wikipedia	License
Coenzyme A (CoA, SHCoA, CoASH) is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. All genomes sequenced to date encode enzymes that use coenzyme A as a substrate, and around 4% of cellular enzymes use it (or a thioester) as a substrate. In humans, CoA biosynthesis requires cysteine, pantothenate (vitamin B5), and adenosine triphosphate (ATP). In its acetyl form, coenzyme A is a highly versatile molecule, serving metabolic functions in both the anabolic and catabolic pathways. Acetyl-CoA is utilised in the post-translational regulation and allosteric regulation of pyruvate dehydrogenase and carboxylase to maintain and support the partition of pyruvate synthesis and degradation.
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Formula

C4H9NO3

Net Charge

Average Mass

119.11920

Monoisotopic Mass

119.05824

InChI

InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1

InChIKey

UKAUYVFTDYCKQA-VKHMYHEASA-N

SMILES

N[C@@H](CCO)C(O)=O

Metabolite of Species	Details
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via homoserine )

ChEBI Ontology
Outgoing	L-homoserine (CHEBI:15699) has role Escherichia coli metabolite (CHEBI:76971) L-homoserine (CHEBI:15699) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) L-homoserine (CHEBI:15699) has role algal metabolite (CHEBI:84735) L-homoserine (CHEBI:15699) has role human metabolite (CHEBI:77746) L-homoserine (CHEBI:15699) is a homoserine (CHEBI:30653) L-homoserine (CHEBI:15699) is enantiomer of D-homoserine (CHEBI:30654) L-homoserine (CHEBI:15699) is tautomer of L-homoserine zwitterion (CHEBI:57476)

Incoming	N-(octanoyl)-L-homoserine (CHEBI:74404) has functional parent L-homoserine (CHEBI:15699) N-heptanoyl-L-homoserine (CHEBI:85607) has functional parent L-homoserine (CHEBI:15699) O-acetyl-L-homoserine (CHEBI:16288) has functional parent L-homoserine (CHEBI:15699) L-canaline (CHEBI:41401) has functional parent L-homoserine (CHEBI:15699) L-canavanine (CHEBI:609827) has functional parent L-homoserine (CHEBI:15699) isonocardicin A (CHEBI:16483) has functional parent L-homoserine (CHEBI:15699) isonocardicin C (CHEBI:81022) has functional parent L-homoserine (CHEBI:15699) D-homoserine (CHEBI:30654) is enantiomer of L-homoserine (CHEBI:15699) L-homoserine zwitterion (CHEBI:57476) is tautomer of L-homoserine (CHEBI:15699)

IUPAC Name

L-homoserine

Synonyms	Sources
(2S)-2-amino-4-hydroxybutanoic acid	IUPAC
2-Amino-4-hydroxybutanoic acid	HMDB
2-Amino-4-hydroxybutyric acid	KEGG COMPOUND
Homoserine	HMDB
L-Homoserine	KEGG COMPOUND
L-HOMOSERINE	PDBeChem

Citation	Type	Source
22770225	PubMed citation	Europe PMC

Last Modified

25 February 2020