CHEBI:33404 - 3-hydroxypropionic acid

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ChEBI Name 3-hydroxypropionic acid
ChEBI ID CHEBI:33404
Definition A 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40000, CHEBI:1553, CHEBI:20071
Supplier Information ChemicalBook:CB6711580, eMolecules:969371, ZINC000000895452
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Formula C3H6O3
Net Charge 0
Average Mass 90.07794
Monoisotopic Mass 90.03169
InChI InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
InChIKey ALRHLSYJTWAHJZ-UHFFFAOYSA-N
SMILES OCCC(O)=O
Roles Classification
Chemical Role(s): 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.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3-hydroxypropionic acid (CHEBI:33404) has functional parent propionic acid (CHEBI:30768)
3-hydroxypropionic acid (CHEBI:33404) has role Escherichia coli metabolite (CHEBI:76971)
3-hydroxypropionic acid (CHEBI:33404) has role human metabolite (CHEBI:77746)
3-hydroxypropionic acid (CHEBI:33404) is a ω-hydroxy-short-chain fatty acid (CHEBI:194306)
3-hydroxypropionic acid (CHEBI:33404) is a 3-hydroxy monocarboxylic acid (CHEBI:35969)
3-hydroxypropionic acid (CHEBI:33404) is conjugate acid of 3-hydroxypropionate (CHEBI:16510)
Incoming β-propiolactone (CHEBI:49073) has functional parent 3-hydroxypropionic acid (CHEBI:33404)
3-(3-hydroxyphenyl)-3-hydroxypropanoic acid (CHEBI:86369) has functional parent 3-hydroxypropionic acid (CHEBI:33404)
3-hydroxypropanoyl-CoA (CHEBI:27762) has functional parent 3-hydroxypropionic acid (CHEBI:33404)
ascr#5 (CHEBI:78829) has functional parent 3-hydroxypropionic acid (CHEBI:33404)
3-hydroxypropionate (CHEBI:16510) is conjugate base of 3-hydroxypropionic acid (CHEBI:33404)
IUPAC Name
3-hydroxypropanoic acid
Synonyms Sources
3-HYDROXY-PROPANOIC ACID PDBeChem
3-Hydroxypropanoic acid KEGG COMPOUND
3-Hydroxypropionic acid KEGG COMPOUND
β-hydroxypropionic acid ChemIDplus
Hydracrylic acid KEGG COMPOUND
Manual Xrefs Databases
3OH PDBeChem
C01013 KEGG COMPOUND
DB03688 DrugBank
HMDB0000700 HMDB
LMFA01050003 LIPID MAPS
View more database links
Registry Numbers Types Sources
26307 Gmelin Registry Number Gmelin
503-66-2 CAS Registry Number KEGG COMPOUND
503-66-2 CAS Registry Number ChemIDplus
773806 Reaxys Registry Number Reaxys
Citations
Kumar V, Ashok S, Park S (2013)
Recent advances in biological production of 3-hydroxypropionic acid.
Biotechnology advances 31, 945-961 [PubMed:23473969]
[show Abstract]
Wang X, Sa N, Wang FH, Tian PF (2013)
Engineered constitutive pathway in Klebsiella pneumoniae for 3-hydroxypropionic acid production and implications for decoupling glycerol dissimilation pathways.
Current microbiology 66, 293-299 [PubMed:23192305]
[show Abstract]
Ashok S, Mohan Raj S, Ko Y, Sankaranarayanan M, Zhou S, Kumar V, Park S (2013)
Effect of puuC overexpression and nitrate addition on glycerol metabolism and anaerobic 3-hydroxypropionic acid production in recombinant Klebsiella pneumoniae ΔglpKΔdhaT.
Metabolic engineering 15, 10-24 [PubMed:23022570]
[show Abstract]
Rathnasingh C, Raj SM, Lee Y, Catherine C, Ashok S, Park S (2012)
Production of 3-hydroxypropionic acid via malonyl-CoA pathway using recombinant Escherichia coli strains.
Journal of biotechnology 157, 633-640 [PubMed:21723339]
[show Abstract]
Linhart I, Hrabal R, Smejkal J, Mitera J (1994)
Metabolic pathways of 1-butyl [3-13C]acrylate. Identification of urinary metabolites in rat using nuclear magnetic resonance and mass spectroscopy.
Chemical research in toxicology 7, 1-8 [PubMed:8155818]
[show Abstract]
Last Modified
24 January 2023