ContaminantDB: Hydroxypropionic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:17:33 UTC

Update Date

2026-04-04 02:21:28 UTC

Accession Number

CHEM003264

Identification

Common Name

Hydroxypropionic acid

Class

Small 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

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

Synonyms

Value	Source
3-HYDROXY-propanoIC ACID	ChEBI
3-Hydroxypropanoic acid	ChEBI
beta-Hydroxypropionic acid	ChEBI
Hydracrylic acid	ChEBI
3-Hydroxypropionate	Kegg
3-Hydroxypropionic acid	Kegg
3-HYDROXY-propanoate	Generator
3-Hydroxypropanoate	Generator
b-Hydroxypropionate	Generator
b-Hydroxypropionic acid	Generator
beta-Hydroxypropionate	Generator
Β-hydroxypropionate	Generator
Β-hydroxypropionic acid	Generator
Hydracrylate	Generator
Hydroxypropionate	Generator
2-Deoxyglycerate	HMDB
2-Deoxyglyceric acid	HMDB
b-Lactate	HMDB
b-Lactic acid	HMDB
beta-Lactate	HMDB
beta-Lactic acid	HMDB
Ethylenelactate	HMDB
Ethylenelactic acid	HMDB

Chemical Formula

C₃H₆O₃

Average Molecular Mass

90.078 g/mol

Monoisotopic Mass

90.032 g/mol

CAS Registry Number

503-66-2

IUPAC Name

3-hydroxypropanoic acid

Traditional Name

hydroxypropionic acid

SMILES

OCCC(O)=O

InChI Identifier

InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)

InChI Key

ALRHLSYJTWAHJZ-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.

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Propanoate Metabolism	SMP00016	map00640
Biotinidase Deficiency	SMP00174	Not Available
Malonic Aciduria	SMP00198	Not Available
Methylmalonate Semialdehyde Dehydrogenase Deficiency	SMP00384	Not Available
Methylmalonic Aciduria	SMP00200	Not Available
Methylmalonic Aciduria Due to Cobalamin-Related Disorders	SMP00201	Not Available
Propionic Acidemia	SMP00236	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	< 25°C
Boiling Point	143°C (sodium salt) decomposes
Solubility	Not Available

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-26c10a7c09d2819f18b3	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fba-0900000000-8bf04c0af8fd2e3b58de	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-26c10a7c09d2819f18b3	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fba-0900000000-8bf04c0af8fd2e3b58de	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9000000000-9aeb0d9c81f19a27c424	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0100-9720000000-bbec0186b2d36c22228d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9000000000-3f5b72b8462bfcb4f391	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-3e9fa999dd5a46584db4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03fu-5900000000-bd7d31d2678f47785461	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-d440d21b0f161a9853f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4r-9000000000-242c99f8bca595fe224e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-052f-9000000000-a9bac0e4116df119abb1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-081d862d9b4bc28ae21b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-be05ae87088e43aa060d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-d440d21b0f161a9853f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9000000000-dba7e70fabc7dac6fe4b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-052f-9000000000-a9bac0e4116df119abb1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-081d862d9b4bc28ae21b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-be05ae87088e43aa060d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-9000000000-abdb98d8c1686dc43cc3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-7e9710b33d0c0f60adc0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9000000000-8076ca0477f5e951c57d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-9000000000-74725037ead28bc3cbb5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-029l-9000000000-e17da766d94d48429d67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-e19c639a151e1fca0d34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-9e7369e67b8849650d52	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fs-9000000000-6bc03f735cf4358adaaf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05di-9000000000-8c197b7691bbbacb263a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-1983baaf50a36f58c36c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-9000000000-5cc8fd5907f4674c72f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9000000000-3e0c27682d8f7902d021	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

3-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)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

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.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB03688

HMDB ID

HMDB0000700

FooDB ID