Showing Compound Hydroxypropionic acid (FDB022189)

Record Information

Version

1.0

Creation date

2011-09-21 00:09:50 UTC

Update date

2020-04-21 18:03:24 UTC

Primary ID

FDB022189

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Hydroxypropionic acid

Description

Hydroxypropionic acid, also known as 3-hydroxypropionate or hydracrylic acid, 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. Hydroxypropionic acid exists in all living organisms, ranging from bacteria to humans. Hydroxypropionic acid has been detected, but not quantified in, several different foods, such as american pokeweeds (Phytolacca americana), garlics (Allium sativum), half-highbush blueberries (Vaccinium angustifolium X Vaccinium corymbosum), breadfruits (Artocarpus altilis), and kiwis (Actinidia chinensis). This could make hydroxypropionic acid a potential biomarker for the consumption of these foods. Hydroxypropionic acid, with regard to humans, has been found to be associated with several diseases such as branched-chain keto acid dehydrogenase kinase deficiency, eosinophilic esophagitis, and stomach cancer; hydroxypropionic acid has also been linked to several inborn metabolic disorders including propionic acidemia and biotinidase deficiency. Based on a literature review a significant number of articles have been published on Hydroxypropionic acid.

CAS Number

503-66-2

Structure

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

Synonyms

Synonym	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
β-hydroxypropionate	Generator
β-hydroxypropionic acid	Generator

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C3H6O3

IUPAC name

3-hydroxypropanoic acid

InChI Identifier

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

InChI Key

ALRHLSYJTWAHJZ-UHFFFAOYSA-N

Isomeric SMILES

OCCC(O)=O

Average Molecular Weight

90.0779

Monoisotopic Molecular Weight

90.031694058

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.

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 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Hydroxypropionic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-26c10a7c09d2819f18b3	Spectrum
GC-MS	Hydroxypropionic acid, non-derivatized, GC-MS Spectrum	splash10-0fba-0900000000-8bf04c0af8fd2e3b58de	Spectrum
GC-MS	Hydroxypropionic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-26c10a7c09d2819f18b3	Spectrum
GC-MS	Hydroxypropionic acid, non-derivatized, GC-MS Spectrum	splash10-0fba-0900000000-8bf04c0af8fd2e3b58de	Spectrum
Predicted GC-MS	Hydroxypropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0007-9000000000-9aeb0d9c81f19a27c424	Spectrum
Predicted GC-MS	Hydroxypropionic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0100-9720000000-bbec0186b2d36c22228d	Spectrum
Predicted GC-MS	Hydroxypropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxypropionic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxypropionic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxypropionic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxypropionic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxypropionic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9000000000-3f5b72b8462bfcb4f391	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-3e9fa999dd5a46584db4	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03fu-5900000000-bd7d31d2678f47785461	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-d440d21b0f161a9853f1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4r-9000000000-242c99f8bca595fe224e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-052f-9000000000-a9bac0e4116df119abb1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-081d862d9b4bc28ae21b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-be05ae87088e43aa060d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-d440d21b0f161a9853f1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9000000000-dba7e70fabc7dac6fe4b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-052f-9000000000-a9bac0e4116df119abb1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-081d862d9b4bc28ae21b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-be05ae87088e43aa060d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-9000000000-abdb98d8c1686dc43cc3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-7e9710b33d0c0f60adc0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9000000000-8076ca0477f5e951c57d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-9000000000-74725037ead28bc3cbb5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-029l-9000000000-e17da766d94d48429d67	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-e19c639a151e1fca0d34	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-9e7369e67b8849650d52	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fs-9000000000-6bc03f735cf4358adaaf	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05di-9000000000-8c197b7691bbbacb263a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-1983baaf50a36f58c36c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-9000000000-5cc8fd5907f4674c72f3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9000000000-3e0c27682d8f7902d021	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum