Showing Compound 1,2,3-Propanetricarboxylic acid (FDB003213)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:42 UTC

Update date

2025-11-18 22:48:45 UTC

Primary ID

FDB003213

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1,2,3-Propanetricarboxylic acid

Description

Isolated from plants e.g. sugarbeet sap, sap of Acer saccharinum (maple syrup) Propane-1,2,3-tricarboxylic acid, also known as tricarballylic acid, carballylic acid, and beta-carboxyglutaric acid, is a tricarboxylic acid that has three carboxylic acid functional groups. The compound is an inhibitor of the enzyme aconitase and interferes with the Krebs cycle. 1,2,3-Propanetricarboxylic acid is found in red beetroot, root vegetables, and corn.

CAS Number

99-14-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3-Carboxyglutaric acid	ChEBI
3-Carboxypentanedioic acid	ChEBI
beta-Carboxyglutaric acid	ChEBI
Carballylic acid	ChEBI
Carboxymethylsuccinic acid	ChEBI
Tricarballylate	Kegg
3-Carboxyglutarate	Generator
3-Carboxypentanedioate	Generator
b-Carboxyglutarate	Generator
b-Carboxyglutaric acid	Generator
beta-Carboxyglutarate	Generator
Β-carboxyglutarate	Generator
Β-carboxyglutaric acid	Generator
Carballylate	Generator
Carboxymethylsuccinate	Generator
Tricarballylic acid	Generator
1,2,3-Propanetricarboxylate	Generator
1,2,3-Tripropanetricarboxylic acid	HMDB
Propane 1,2,3-tricarboxylic acid	HMDB
Tricarballylic acid, trisodium salt	MeSH, HMDB
Propane-1,2,3-tricarboxylate	MeSH, HMDB
Tricarballylic acid, sodium salt	MeSH, HMDB
1,2,3-Propanetricarboxylic acid	ChEBI
Beta-carboxyglutaric acid	biospider
β-carboxyglutarate	Generator
β-carboxyglutaric acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	37.8 g/L	ALOGPS
logP	-0.56	ALOGPS
logP	-0.73	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	3.59	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	34.38 m³·mol⁻¹	ChemAxon
Polarizability	14.79 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

C6H8O6

IUPAC name

propane-1,2,3-tricarboxylic acid

InChI Identifier

InChI=1S/C6H8O6/c7-4(8)1-3(6(11)12)2-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

InChI Key

KQTIIICEAUMSDG-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

176.1241

Monoisotopic Molecular Weight

176.032087988

Classification

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tricarboxylic acid (CHEBI:45969 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Fusarium verticilloides

Microbe:

Wolinella:

Wolinella succinogenes

Megasphaera:

Megasphaera elsdenii

Bacteroides:

Bacteroides ruminicola

Butyrivibrio:

Butyrivibrio fibrisolvens

Plant:

Poaceae

Biological location:

Biofluid and excreta:

Feces

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 40.92%; H 4.58%; O 54.50%	DFC
Melting Point	Mp 166°	DFC
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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-01p6-9200000000-49fb526d0b36a4723f55	2015-03-01	View Spectrum
Predicted GC-MS	1,2,3-Propanetricarboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-5900000000-71d0f07709d92d993b77	Spectrum
Predicted GC-MS	1,2,3-Propanetricarboxylic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00b9-9154000000-a5760521d0e943c5a188	Spectrum
Predicted GC-MS	1,2,3-Propanetricarboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,3-Propanetricarboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2900000000-09ae1148bf0e5924cd86	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014r-9100000000-222cb35a32f888421db7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-89281ca5096f1def31a5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004r-9500000000-2be0c267efe352a03236	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-002r-6900000000-07615c72f45a8c1af8f1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-3900000000-30c6cb52a165f67adc79	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-6900000000-b5059f3f2bed0f835b21	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-057i-0900000000-ca7860b303dcd2f2c2e7	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00m0-4900000000-096c308c50609212658c	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9200000000-504813f916f35f099fd4	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-1900000000-75e14da97e618b8087db	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0040-3900000000-74e5a6e0a0b40c87e001	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9200000000-62af859e2a81f90f8b55	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9100000000-2d50b55dedd12855fe01	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9300000000-9771ed0fd1268ec64531	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-bd85aa22caa1da35ab86	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06r6-0900000000-5a19b6ded794c8ac5a9c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-029i-5900000000-f9d16e54ccf2b042be60	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-9000000000-15c9b1294cfa6364b10b	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum