Hydroxypropionic acid (CHEM003264)

Record Information
Version1.0
Creation Date2014-08-29 06:17:33 UTC
Update Date2026-05-14 17:51:16 UTC
Accession NumberCHEM003264
Identification
Common NameHydroxypropionic acid
ClassSmall Molecule
Description
3-Hydroxypropionic acid is a carboxylic acid. It is used in the production of various chemicals such as acrylates in industry. It can be produced by certain microbes. Its chemical structure is similar to L-serine.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-HYDROXY-propanoIC ACIDChEBI
3-Hydroxypropanoic acidChEBI
beta-Hydroxypropionic acidChEBI
Hydracrylic acidChEBI
3-HydroxypropionateKegg
3-Hydroxypropionic acidKegg
3-HYDROXY-propanoateGenerator
3-HydroxypropanoateGenerator
b-HydroxypropionateGenerator
b-Hydroxypropionic acidGenerator
beta-HydroxypropionateGenerator
Β-hydroxypropionateGenerator
Β-hydroxypropionic acidGenerator
HydracrylateGenerator
HydroxypropionateGenerator
2-DeoxyglycerateHMDB
2-Deoxyglyceric acidHMDB
b-LactateHMDB
b-Lactic acidHMDB
beta-LactateHMDB
beta-Lactic acidHMDB
EthylenelactateHMDB
Ethylenelactic acidHMDB
Chemical FormulaC3H6O3
Average Molecular Mass90.078 g/mol
Monoisotopic Mass90.032 g/mol
CAS Registry Number503-66-2
IUPAC Name3-hydroxypropanoic acid
Traditional Namehydroxypropionic acid
SMILESOCCC(O)=O
InChI IdentifierInChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
InChI KeyALRHLSYJTWAHJZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Propanoate MetabolismSMP00016 map00640
Biotinidase DeficiencySMP00174 Not Available
Malonic AciduriaSMP00198 Not Available
Methylmalonate Semialdehyde Dehydrogenase DeficiencySMP00384 Not Available
Methylmalonic AciduriaSMP00200 Not Available
Methylmalonic Aciduria Due to Cobalamin-Related DisordersSMP00201 Not Available
Propionic AcidemiaSMP00236 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< 25°C
Boiling Point143°C (sodium salt) decomposes
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility647 g/LALOGPS
logP-0.95ALOGPS
logP-0.8ChemAxon
logS0.86ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.05 m³·mol⁻¹ChemAxon
Polarizability8.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of Toxicity3-hydroxypropionic acid (3HP) toxicity is mediated by 3-hydroxypropionic aldehyde (reuterin). 3HP toxicity is also proposed to be related to inhibition of the chorismate and threonine super-pathways. Generally, the toxicity mechanism of 3HP is not understood at the molecular level. (6)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsChronically high levels of hydroxypropionic acid are associated with at least 5 inborn errors of metabolism including: Biotinidase deficiency, Malonic Aciduria, Methylmalonate Semialdehyde Dehydrogenase Deficiency, Methylmalonic Aciduria, Methylmalonic, Aciduria Due to Cobalamin-Related Disorders and Propionic acidemia.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB03688
HMDB IDHMDB0000700
FooDB IDFDB022189
Phenol Explorer IDNot Available
KNApSAcK IDC00052684
BiGG ID53188
BioCyc ID3-HYDROXY-PROPIONATE
METLIN ID5668
PDB IDNot Available
Wikipedia LinkHydroxypropanoic acid
Chemspider ID61460
ChEBI ID33404
PubChem Compound ID68152
Kegg Compound IDC01013
YMDB IDNot Available
ECMDB IDECMDB21168
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21723339
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23022570
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23192305
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23473969
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8155818
6. Suthers, Patrick F.; Cameron, Douglas C. Production of 3-hydroxypropionic acid in recombinant organisms. PCT Int. Appl. (2001), 63 pp.
7. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6.
8. Sweetman L, Bates SP, Hull D, Nyhan WL: Propionyl-CoA carboxylase deficiency in a patient with biotin-responsive 3-methylcrotonylglycinuria. Pediatr Res. 1977 Nov;11(11):1144-7.
9. Pollitt RJ, Fowler B, Sardharwalla IB, Edwards MA, Gray RG: Increased excretion of propan-1,3-diol and 3-hydroxypropionic acid apparently caused by abnormal bacterial metabolism in the gut. Clin Chim Acta. 1987 Nov 16;169(2-3):151-7.
10. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69.
11. Brown GK, Cromby CH, Manning NJ, Pollitt RJ: Urinary organic acids in succinic semialdehyde dehydrogenase deficiency: evidence of alpha-oxidation of 4-hydroxybutyric acid, interaction of succinic semialdehyde with pyruvate dehydrogenase and possible secondary inhibition of mitochondrial beta-oxidation. J Inherit Metab Dis. 1987;10(4):367-75.
12. Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8.