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Record Information
Version	2.0
Creation Date	2012-07-30 14:54:44 -0600
Update Date	2015-09-13 15:15:31 -0600
Secondary Accession Numbers	ECMDB21168
Identification
Name:	3-Hydroxypropanoate
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.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xad1f743c> Close
Synonyms:	β-hydroxypropionate β-hydroxypropionic acid 2-Deoxyglycerate 2-Deoxyglyceric acid 3-Hydropropionate 3-Hydropropionic acid 3-Hydroxyisobutyrate 3-Hydroxyisobutyric acid 3-Hydroxypropanoate 3-Hydroxypropanoic acid 3-Hydroxypropenoate 3-Hydroxypropenoic acid 3-Hydroxypropionate 3-Hydroxypropionic acid B-Hydroxypropionate B-Hydroxypropionic acid B-Lactate B-Lactic acid Beta-Hydroxypropionate Beta-Hydroxypropionic acid Beta-Lactate Beta-Lactic acid Ethylenelactate Ethylenelactic acid Hydracrylate Hydracrylic acid Hydroxypropionate Hydroxypropionic acid β-Hydroxypropionate β-Hydroxypropionic acid β-Lactate β-Lactic acid
Chemical Formula:	C3H6O3
Weight:	Average: 90.0779 Monoisotopic: 90.031694058
InChI Key:	ALRHLSYJTWAHJZ-UHFFFAOYSA-N
InChI:	InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
CAS number:	503-66-2
IUPAC Name:	3-hydroxypropanoic acid
Traditional IUPAC Name:	hydroxypropionic acid
SMILES:	OCCC(O)=O
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Hydroxy acids and derivatives
Sub Class	Beta hydroxy acids and derivatives
Direct Parent	Beta hydroxy acids and derivatives
Alternative Parents	Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	3-hydroxy monocarboxylic acid (CHEBI:33404 ) omega-hydroxy fatty acid (CHEBI:33404 )
Physical Properties
State:	Liquid
Charge:	-1
Melting point:	<25°C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 647 g/L ALOGPS logP -0.95 ALOGPS logP -0.8 ChemAxon logS 0.86 ALOGPS pKa (Strongest Acidic) 4.2 ChemAxon pKa (Strongest Basic) -2.5 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 57.53 Ų ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 19.05 m³·mol⁻¹ ChemAxon Polarizability 8.15 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Hydrogen ion + Malonic semialdehyde + NADPH > 3-Hydroxypropanoate + NADP 3-Hydroxypropanoate + NADP <> Malonic semialdehyde + NADPH + Hydrogen ion 3-Hydroxypropanoate + NADP < Malonic semialdehyde + NADPH + Hydrogen ion 3-hydroxypropionaldehyde + NAD + Water > Hydrogen ion + 3-Hydroxypropanoate + NADH 3-Hydroxypropanoate + NADP > Malonic semialdehyde + NADPH Hydrogen ion + Malonic semialdehyde + NADPH >3 3-Hydroxypropanoate + NADP Hydrogen ion + Malonic semialdehyde + NADPH >3 3-Hydroxypropanoate + NADP
SMPDB Pathways:	Uracil degradation III PW002026
KEGG Pathways:	Not Available
EcoCyc Pathways:	uracil degradation III PWY0-1471
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0002-0900000000-26c10a7c09d2819f18b3 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0fba-0900000000-8bf04c0af8fd2e3b58de View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0002-0900000000-26c10a7c09d2819f18b3 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0fba-0900000000-8bf04c0af8fd2e3b58de View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0007-9000000000-9aeb0d9c81f19a27c424 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-0100-9720000000-bbec0186b2d36c22228d View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-00di-9000000000-3f5b72b8462bfcb4f391 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-00di-9000000000-3e9fa999dd5a46584db4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-03fu-5900000000-bd7d31d2678f47785461 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-000i-9000000000-d440d21b0f161a9853f1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-0a4r-9000000000-242c99f8bca595fe224e View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-052f-9000000000-a9bac0e4116df119abb1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-0006-9000000000-081d862d9b4bc28ae21b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-0006-9000000000-be05ae87088e43aa060d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-000i-9000000000-d440d21b0f161a9853f1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0a4r-9000000000-dba7e70fabc7dac6fe4b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-052f-9000000000-a9bac0e4116df119abb1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0006-9000000000-081d862d9b4bc28ae21b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0006-9000000000-be05ae87088e43aa060d View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-01ox-9000000000-abdb98d8c1686dc43cc3 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-03di-9000000000-7e9710b33d0c0f60adc0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-00kf-9000000000-8076ca0477f5e951c57d View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-03dl-9000000000-74725037ead28bc3cbb5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-029l-9000000000-e17da766d94d48429d67 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-03di-9000000000-e19c639a151e1fca0d34 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00di-9000000000-9e7369e67b8849650d52 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-05fs-9000000000-6bc03f735cf4358adaaf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-05di-9000000000-8c197b7691bbbacb263a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-9000000000-1983baaf50a36f58c36c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00dr-9000000000-5cc8fd5907f4674c72f3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-006x-9000000000-3e0c27682d8f7902d021 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	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 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 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 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 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 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
Synthesis Reference:	Suthers, 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)
Links
External Links:	Resource Link CHEBI ID 16510 HMDB ID HMDB00700 Pubchem Compound ID 5459847 Kegg ID C01013 ChemSpider ID 61460 Wikipedia ID Hydroxypropanoic acid BioCyc ID 3-HYDROXY-PROPIONATE EcoCyc ID 3-HYDROXY-PROPIONATE Ligand Expo 3OH

Enzymes

Transporters