ECMDB: 3-Hydroxypropanoate (ECMDB21168) (M2MDB001577)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)Transporters (4)XML

Proteins (111)

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

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 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	19.05 m³·mol⁻¹	ChemAxon
Polarizability	8.15 Å³	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

Protein Details

1. Gamma-glutamyl-gamma-aminobutyraldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Involved in the breakdown of putrescine. Was previously shown to have a weak but measurable ALDH enzyme activity that prefers NADP over NAD as coenzyme
Gene Name:: puuC
Uniprot ID:: P23883
Molecular weight:: 53418

Reactions

Gamma-glutamyl-gamma-aminobutyraldehyde + NAD(+) + H(2)O = gamma-glutamyl-gamma-aminobutyrate + NADH.
An aldehyde + NAD(P)(+) + H(2)O = a carboxylate + NAD(P)H.

Protein Details

2. Putative NADH dehydrogenase/NAD(P)H nitroreductase rutE

General function:: Involved in oxidoreductase activity
Specific function:: Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:: rutE
Uniprot ID:: P75894
Molecular weight:: 21570

Reactions

3-hydroxypropanoate + NADP(+) = 3-oxopropanoate + NADPH.

Protein Details

3. NADP-dependent L-serine/L-allo-threonine dehydrogenase ydfG

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADP-dependent oxidation of L-allo- threonine to L-2-amino-3-keto-butyrate, which is spontaneously decarboxylated into aminoacetone. Also acts on L-serine, D-serine, D-threonine, D-3-hydroxyisobutyrate, L-3-hydroxyisobutyrate, D- glycerate and L-glycerate
Gene Name:: ydfG
Uniprot ID:: P39831
Molecular weight:: 27249

Reactions

3-hydroxypropanoate + NADP(+) = 3-oxopropanoate + NADPH.

Transporters

Protein Details

1. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

2. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

3. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

4. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

3-Hydroxypropanoate (ECMDB21168) (M2MDB001577)

Structure for #<Compound:0xa41574e0>

Enzymes

Reactions

Reactions

Reactions

Transporters