Record Information
Version1.0
Creation date2015-05-07 19:14:26 UTC
Update date2019-11-26 03:21:44 UTC
Primary IDFDB030432
Secondary Accession Numbers
  • FDB022189
Chemical Information
FooDB Name3-hydroxypropionate
DescriptionHydroxypropionic acid, also known as 3-hydroxypropionate or hydracrylic acid, belongs to beta hydroxy acids and derivatives class of compounds. Those are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Hydroxypropionic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Hydroxypropionic acid can be synthesized from propionic acid. Hydroxypropionic acid is also a parent compound for other transformation products, including but not limited to, beta-propiolactone, ascr#5, and 3-hydroxypropanoyl-CoA. Hydroxypropionic acid can be found in a number of food items such as apple, poppy, yam, and cupuaçu, which makes hydroxypropionic acid a potential biomarker for the consumption of these food products. Hydroxypropionic acid can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine. Hydroxypropionic acid exists in all living organisms, ranging from bacteria to humans. In humans, hydroxypropionic acid is involved in the propanoate metabolism. Hydroxypropionic acid is also involved in few metabolic disorders, which include malonic aciduria, malonyl-coa decarboxylase deficiency, and methylmalonic aciduria due to cobalamin-related disorders. Moreover, hydroxypropionic acid is found to be associated with biotinidase deficiency and propionic acidemia. Hydroxypropionic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Hydroxypropanoic acid, or alternately hydroxypropionic acid, may refer to either of two isomeric chemical compounds: 3-Hydroxypropionic acid (hydracrylic acid) Lactic acid (2-hydroxypropanoic acid) . Chronically 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 (T3DB).
CAS Number503-66-2
Structure
Thumb
Synonyms
SynonymSource
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
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
Chemical FormulaC3H6O3
IUPAC name3-hydroxypropanoic acid
InChI IdentifierInChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
InChI KeyALRHLSYJTWAHJZ-UHFFFAOYSA-N
Isomeric SMILESOCCC(O)=O
Average Molecular Weight90.0779
Monoisotopic Molecular Weight90.031694058
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSHydroxypropionic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-26c10a7c09d2819f18b3Spectrum
GC-MSHydroxypropionic acid, non-derivatized, GC-MS Spectrumsplash10-0fba-0900000000-8bf04c0af8fd2e3b58deSpectrum
GC-MSHydroxypropionic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-26c10a7c09d2819f18b3Spectrum
GC-MSHydroxypropionic acid, non-derivatized, GC-MS Spectrumsplash10-0fba-0900000000-8bf04c0af8fd2e3b58deSpectrum
Predicted GC-MSHydroxypropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-9000000000-9aeb0d9c81f19a27c424Spectrum
Predicted GC-MSHydroxypropionic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0100-9720000000-bbec0186b2d36c22228dSpectrum
Predicted GC-MSHydroxypropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHydroxypropionic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHydroxypropionic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHydroxypropionic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHydroxypropionic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHydroxypropionic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-3f5b72b8462bfcb4f3912012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-3e9fa999dd5a46584db42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03fu-5900000000-bd7d31d2678f477854612012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-d440d21b0f161a9853f12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4r-9000000000-242c99f8bca595fe224e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052f-9000000000-a9bac0e4116df119abb12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-081d862d9b4bc28ae21b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-be05ae87088e43aa060d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-d440d21b0f161a9853f12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4r-9000000000-dba7e70fabc7dac6fe4b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052f-9000000000-a9bac0e4116df119abb12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-081d862d9b4bc28ae21b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-be05ae87088e43aa060d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9000000000-abdb98d8c1686dc43cc32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-7e9710b33d0c0f60adc02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9000000000-8076ca0477f5e951c57d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03dl-9000000000-74725037ead28bc3cbb52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-029l-9000000000-e17da766d94d48429d672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-e19c639a151e1fca0d342021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-9e7369e67b8849650d522015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-9000000000-6bc03f735cf4358adaaf2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05di-9000000000-8c197b7691bbbacb263a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-1983baaf50a36f58c36c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-9000000000-5cc8fd5907f4674c72f32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9000000000-3e0c27682d8f7902d0212015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference