You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 18:16:12 UTC
HMDB IDHMDB0000700
Secondary Accession Numbers
  • HMDB00700
Metabolite Identification
Common NameHydroxypropionic acid
Description3-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.
Structure
Thumb
Synonyms
ValueSource
3-HYDROXY-propanoIC ACIDChEBI
3-Hydroxypropanoic acidChEBI
beta-Hydroxypropionic acidChEBI
Hydracrylic acidChEBI
3-HYDROXY-propanoateGenerator
HydroxypropionateGenerator
3-HydroxypropanoateGenerator
b-HydroxypropionateGenerator
b-Hydroxypropionic acidGenerator
beta-HydroxypropionateGenerator
β-hydroxypropionateGenerator
β-hydroxypropionic acidGenerator
HydracrylateGenerator
2-DeoxyglycerateHMDB
2-Deoxyglyceric acidHMDB
3-HydroxypropionateHMDB
3-Hydroxypropionic acidHMDB
b-LactateHMDB
b-Lactic acidHMDB
beta-LactateHMDB
beta-Lactic acidHMDB
EthylenelactateHMDB
Ethylenelactic acidHMDB
Chemical FormulaC3H6O3
Average Molecular Weight90.0779
Monoisotopic Molecular Weight90.031694058
IUPAC Name3-hydroxypropanoic acid
Traditional Namehydroxypropionic acid
CAS Registry Number503-66-2
SMILES
OCCC(O)=O
InChI Identifier
InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
InChI KeyALRHLSYJTWAHJZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassHydroxy 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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-26c10a7c09d2819f18b3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fba-0900000000-8bf04c0af8fd2e3b58deView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9000000000-9aeb0d9c81f19a27c424View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0100-9720000000-bbec0186b2d36c22228dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-3f5b72b8462bfcb4f391View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-3e9fa999dd5a46584db4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03fu-5900000000-bd7d31d2678f47785461View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-d440d21b0f161a9853f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4r-9000000000-242c99f8bca595fe224eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052f-9000000000-a9bac0e4116df119abb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-081d862d9b4bc28ae21bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-be05ae87088e43aa060dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-d440d21b0f161a9853f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4r-9000000000-dba7e70fabc7dac6fe4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052f-9000000000-a9bac0e4116df119abb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-081d862d9b4bc28ae21bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-be05ae87088e43aa060dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-9e7369e67b8849650d52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-9000000000-6bc03f735cf4358adaafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05di-9000000000-8c197b7691bbbacb263aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-1983baaf50a36f58c36cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-9000000000-5cc8fd5907f4674c72f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9000000000-3e0c27682d8f7902d021View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Malonic AciduriaPw000207Pw000207 greyscalePw000207 simpleNot Available
Malonyl-coa decarboxylase deficiencyPw000478Pw000478 greyscalePw000478 simpleNot Available
Methylmalonic Aciduria Due to Cobalamin-Related DisordersPw000208Pw000208 greyscalePw000208 simpleNot Available
Propanoate MetabolismPw000149Pw000149 greyscalePw000149 simpleMap00640
Displaying all 4 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.3 (0.0-4.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified4.4 +/- 4.4 uMAdult (>18 years old)Not AvailableNormal details
UrineDetected and Quantified12.3 (4.4-17.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.4-6.6 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified8.1 (3.1-11.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified<15.8 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified11.2 (3.4-33.6) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified13.8 (0.1-48.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified8.3 (2.3-18.3) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified2.3-5.3 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified6.1 (1.5-26.1) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified52.003 +/- 19.151 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
gastric cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified1000.00 (20.00-2000.00) umol/mmol creatinineChildren (1-13 years old)BothPropionic acidemia details
UrineDetected and Quantified6.5 (3.0-10.0) umol/mmol creatinineAdult (>18 years old)BothBiotinidase deficiency details
UrineDetected and Quantified260.0 (20.0-500.0) umol/mmol creatinineChildren (1-13 years old)BothBiotinidase deficiency details
UrineDetected and Quantified51.302 +/- 25.775 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified73.827 +/- 94.707 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Biotinidase deficiency
    MetaGene
Propionic acidemia
    MetaGene
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022189
KNApSAcK IDNot Available
Chemspider ID61460
KEGG Compound IDC01013
BioCyc IDNot Available
BiGG ID53188
Wikipedia LinkHydroxypropionic acid
METLIN ID5668
PubChem Compound68152
PDB ID3OH
ChEBI ID33404
References
Synthesis ReferenceSuthers, Patrick F.; Cameron, Douglas C. Production of 3-hydroxypropionic acid in recombinant organisms. PCT Int. Appl. (2001), 63 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:8087979 ]
  2. 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. [PubMed:8412012 ]
  3. 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. [PubMed:3126356 ]
  4. 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. [PubMed:3427776 ]
  5. 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. [PubMed:917614 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydrolyzes 3-hydroxypropanoyl-CoA.
Gene Name:
HIBCH
Uniprot ID:
Q6NVY1
Molecular weight:
43481.935
Reactions
3-Hydroxypropionyl-CoA + Phosphoric acid + ADP → Hydroxypropionic acid + Coenzyme A + Adenosine triphosphatedetails
Hydroxypropionic acid + Coenzyme A → 3-Hydroxypropionyl-CoA + Waterdetails