Livestock Metabolome Database: Showing metabocard for Malonic acid (LMDB00217)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:44:56 UTC

Update Date

2021-04-30 20:57:58 UTC

Lmdb

LMDB00217

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Malonic acid

Description

Malonic acid, also known as malonate or H2MALO, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Malonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Malonic acid exists in all living species, ranging from bacteria to humans. Within humans, malonic acid participates in a number of enzymatic reactions. In particular, malonic acid and acetic acid can be converted into acetoacetic acid; which is mediated by the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In addition, malonic acid and coenzyme A can be biosynthesized from malonyl-CoA through its interaction with the enzyme fatty acid synthase. malonyl/acetyl transferase domain. An Malonic acid in which the two carboxy groups are separated by a single methylene group. In humans, malonic acid is involved in fatty acid biosynthesis. Outside of the human body, Malonic acid has been detected, but not quantified in, several different foods, such as red beetroots, corns, scarlet beans, common beets, and cow milks. This could make malonic acid a potential biomarker for the consumption of these foods. Malonic acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, combined malonic and methylmalonic aciduria, and early preeclampsia; malonic acid has also been linked to the inborn metabolic disorder malonyl-coa decarboxylase deficiency.

Structure

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

Synonyms

Value	Source
H2Malo	ChEBI
HOOC-CH2-COOH	ChEBI
Propanedioic acid	ChEBI
Propanedioate	Generator
Malonate	Generator
alpha,Omega-dicarboxylic acid	HMDB
Carboxyacetic acid	HMDB
Dicarboxylate	HMDB
Dicarboxylic acid	HMDB
Dicarboxymethane	HMDB
Kyselina malonova	HMDB
Malonate dicarboxylic acid	HMDB
Metahnedicarboxylic acid	HMDB
Methanedicarbonic acid	HMDB
Methanedicarboxylic acid	HMDB
Propanedioic acid dithallium salt	HMDB
Propanediolic acid	HMDB
Thallium malonate	HMDB
Malonic acid, 2-(14)C-labeled	HMDB
Malonic acid, monocalcium salt	HMDB
Malonic acid, 1,3-(14)C2-labeled	HMDB
Malonic acid, diammonium salt	HMDB
Malonic acid, disodium salt	HMDB
Malonic acid, dithallium salt	HMDB
Malonic acid, dipotassium salt	HMDB
Malonic acid, disodium salt, 1-(14)C-labeled	HMDB
Malonic acid, monosodium salt	HMDB
Malonic acid, potassium salt	HMDB
Malonic acid, sodium salt	HMDB
Thallous malonate	HMDB
Dithallium malonate	HMDB
Monosodium malonate	HMDB
Malonic acid	Generator

Chemical Formula

C₃H₄O₄

Average Molecular Weight

104.0615

Monoisotopic Molecular Weight

104.010958616

IUPAC Name

propanedioic acid

Traditional Name

malonic acid

CAS Registry Number

141-82-2

SMILES

OC(=O)CC(O)=O

InChI Identifier

InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)

InChI Key

OFOBLEOULBTSOW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

1,3-dicarbonyl compound
Dicarboxylic 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

alpha,omega-dicarboxylic acid (CHEBI:30794 )
Dicarboxylic acids (LMFA01170041 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.6	ALOGPS
logP	-0.33	ChemAxon
logS	0.28	ALOGPS
pKa (Strongest Acidic)	2.43	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	18.99 m³·mol⁻¹	ChemAxon
Polarizability	8.13 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-1900000000-a1463432c138c328557d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-5e58241137fee0ccc64a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006t-9700000000-54976b3ce8f36ce0676d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-4930000000-e7dbed4919870db8dabf	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-05gl-1943000000-456e387fdf365bf0f8ee	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-6c56a402111059603ba4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-f239df8fdd12e9a74445	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-6865e83f0df5c9831619	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0900000000-a768f0aae86e17a3a6ba	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1900000000-a1463432c138c328557d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-5e58241137fee0ccc64a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-9700000000-54976b3ce8f36ce0676d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-05gl-1943000000-456e387fdf365bf0f8ee	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-4930000000-e7dbed4919870db8dabf	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-a45cfb1e2683f8ad8c5c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0911000000-8b0d7393c5dc4462a756	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfu-9300000000-cbc239877c485e6dff65	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9410000000-c30e36ba8e95ef1c83be	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 (TBDMS_1_1) - 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, Negative (Annotated)	splash10-0a4i-9100000000-c7a1704f8a38ca2d245a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4l-9100000000-9fa84f43f2e19b56035c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-052f-9100000000-8a21753b343cf5dabdcb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0006-9000000000-6c56a402111059603ba4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-f239df8fdd12e9a74445	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-3900000000-e0a4c7e792cfd0e60cc3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-9000000000-4c03aa889e6a98ab532f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4l-9000000000-b3d14c986f292bdcf477	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-8e1041322f9acda4088a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-af4dccf21d68110099a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-3900000000-e0a4c7e792cfd0e60cc3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-4c03aa889e6a98ab532f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9000000000-b3d14c986f292bdcf477	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-8e1041322f9acda4088a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-af4dccf21d68110099a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0006-3900000000-2126168f67ddb43e544d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-9000000000-e9d5906655e37a471b89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-c742107695804ea678f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-cb15cb8d630a4fbd0750	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-7900000000-795ca313c7daaf448ede	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bti-9400000000-a6390568ef61fe1a284e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9100000000-cc17364c6d52c2c208f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-6900000000-b1169abf90c9693f8e30	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9300000000-cec6a47ea3eb4a95a957	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-cffa3dea7855764ea854	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01ox-9000000000-dd4efef191376724d0f1	Spectrum
1D NMR	13C NMR Spectrum	Not Available	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	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
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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Colostrum
Feces
Kidney perfusate
Meat
Milk
Plasma
Ruminal Fluid
Serum
Synovial Fluid
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	22436164	details
Feces	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Kidney perfusate	Detected but not Quantified	Not Applicable	Not Available	Porcine	25502759	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	22436164	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23497994	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25087032	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Serum	Detected and Quantified	16.3484 +/- 3.8063 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.1001 +/- 1.963 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.2089 +/- 2.7708 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.7469 +/- 4.2505 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.3899 +/- 2.8037 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.63 +/- 6.13 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	16.5957 +/- 4.9848 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	15.0341 +/- 2.7774 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.2993 +/- 3.2482 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	15.3768 +/- 4.1824 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.8365 +/- 2.4751 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.7428 +/- 2.995 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	17.4712 +/- 5.7878 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Serum	Detected and Quantified	13.9904 +/- 2.4125 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	17.2653 +/- 5.3174 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.7335 +/- 4.0213 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.9479 +/- 2.1769 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.9786 +/- 2.552 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	15.3202 +/- 3.1758 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.6079 +/- 3.0633 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.6013 +/- 3.8083 uM	Normal	Ovine	Goldansaz et al.,...	details
Synovial Fluid	Detected but not Quantified	Not Applicable	Not Available	Ovine	25283885	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	24696864	details