Showing Compound 3-Hydroxyglutaric acid (FDB022040)

Record Information

Version

1.0

Creation date

2011-09-21 00:07:26 UTC

Update date

2015-10-09 22:33:28 UTC

Primary ID

FDB022040

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Hydroxyglutaric acid

Description

3-Hydroxyglutaric acid, also known as 3-hydroxy-glutarate or 3-hydroxypentanedioic 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. 3-Hydroxyglutaric acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyglutaric acid a potential biomarker for the consumption of these foods. 3-Hydroxyglutaric acid, with regard to humans, has been linked to several inborn metabolic disorders including glutaric aciduria I and glutaryl-coa dehydrogenase deficiency (gdhd). Based on a literature review a significant number of articles have been published on 3-Hydroxyglutaric acid.

CAS Number

638-18-6

Structure

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

Synonyms

Synonym	Source
3-Hydroxy-glutaric acid	ChEBI
beta-Hydroxyglutaric acid	ChEBI
3-Hydroxy-glutarate	Generator
b-Hydroxyglutarate	Generator
b-Hydroxyglutaric acid	Generator
beta-Hydroxyglutarate	Generator
Β-hydroxyglutarate	Generator
Β-hydroxyglutaric acid	Generator
3-Hydroxyglutarate	Generator
3-Hydroxypentanedioic acid	HMDB
2,4-Dideoxypentaric acid	HMDB
3-Hydroxypentanedioate	HMDB
3-Hydroxyglutaric acid	MeSH
3-hydroxy-glutarate	hmdb
3-hydroxy-glutaric acid	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	172 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1	ChemAxon
logS	0.06	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	29.5 m³·mol⁻¹	ChemAxon
Polarizability	12.81 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

C5H8O5

IUPAC name

3-hydroxypentanedioic acid

InChI Identifier

InChI=1S/C5H8O5/c6-3(1-4(7)8)2-5(9)10/h3,6H,1-2H2,(H,7,8)(H,9,10)

InChI Key

ZQHYXNSQOIDNTL-UHFFFAOYSA-N

Isomeric SMILES

OC(CC(O)=O)CC(O)=O

Average Molecular Weight

148.114

Monoisotopic Molecular Weight

148.037173366

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

Short-chain hydroxy acid
Beta-hydroxy acid
Fatty acid
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Aciduria

Metabolism and nutrition disorders:

Glutaric aciduria type 1

Disposition

Source:

Endogenous

Biological location:

Cell and elements:

Cell:

Nerve cell

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Indirect biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
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
Predicted GC-MS	3-Hydroxyglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0536-9200000000-95922095d2aa1db75f8b	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00gs-9081000000-c273d86d7f22986f4bcd	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyglutaric acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-9249b84ab50ffbbbab00	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9100000000-a007a5c975eeaa894298	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0fbi-4900000000-111cef5b8a6a577bf701	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01qa-1900000000-83e00bd7b92b7f2f9832	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qi-5900000000-da4f8a92eae4f7ae9a73	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-a255aedbfaa3bce837b8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-2900000000-6ea9c60bf78cda297a39	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pbj-9800000000-db9f014d4e5dce1cc78f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-89edd1cbe710cf97835d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-9400000000-3231e946df512b24401a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0076-9200000000-4ffdd7ac7861294da783	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9000000000-f46770ad7298e670b4b7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f72-5900000000-c4e9005c7c37f89f6fe3	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052f-9100000000-de505ca4195705703e19	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-cae7897ab9482c2d43bc	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 500 MHz, H₂O, experimental)	Spectrum