MiMeDB: Showing metabocard for Malonic acid (MMDBc0000138)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:37:15 UTC

Update Date

2024-09-29 08:11:48 UTC

Metabolite ID

MMDBc0000138

Metabolite Identification

Common Name

Malonic acid

Description

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionised form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's ethyl ester. The name originates from Latin malum, meaning apple. Malonic acid is the archetypal example of a competitive inhibitor: it acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain. Malonic acid is found to be associated with malonyl-CoA decarboxylase deficiency, which is an inborn error of metabolism.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

Molecular Formula

C₃H₄O₄

Average Mass

104.0615

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	197 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-4930000000-e7dbed4919870db8dabf	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-05gl-1943000000-456e387fdf365bf0f8ee	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-6c56a402111059603ba4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-f239df8fdd12e9a74445	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-6865e83f0df5c9831619	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0900000000-a768f0aae86e17a3a6ba	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1900000000-a1463432c138c328557d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-5e58241137fee0ccc64a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-9700000000-54976b3ce8f36ce0676d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-05gl-1943000000-456e387fdf365bf0f8ee	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-4930000000-e7dbed4919870db8dabf	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-a45cfb1e2683f8ad8c5c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0911000000-8b0d7393c5dc4462a756	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfu-9300000000-cbc239877c485e6dff65	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9410000000-c30e36ba8e95ef1c83be	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-9100000000-c7a1704f8a38ca2d245a	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4l-9100000000-9fa84f43f2e19b56035c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-052f-9100000000-8a21753b343cf5dabdcb	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0006-9000000000-6c56a402111059603ba4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-f239df8fdd12e9a74445	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-3900000000-e0a4c7e792cfd0e60cc3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-9000000000-4c03aa889e6a98ab532f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4l-9000000000-b3d14c986f292bdcf477	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-8e1041322f9acda4088a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-af4dccf21d68110099a1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-3900000000-e0a4c7e792cfd0e60cc3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-4c03aa889e6a98ab532f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9000000000-b3d14c986f292bdcf477	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-8e1041322f9acda4088a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-af4dccf21d68110099a1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0006-3900000000-2126168f67ddb43e544d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-9000000000-e9d5906655e37a471b89	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-c742107695804ea678f1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-cb15cb8d630a4fbd0750	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-7900000000-795ca313c7daaf448ede	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bti-9400000000-a6390568ef61fe1a284e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9100000000-cc17364c6d52c2c208f3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-6900000000-b1169abf90c9693f8e30	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9300000000-cec6a47ea3eb4a95a957	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-cffa3dea7855764ea854	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01ox-9000000000-dd4efef191376724d0f1	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)		2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Kidney
Liver
Saliva
Urine

Tissue Locations

Kidney
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191918	4-aminobutyrate aminotransferase, mitochondrial	Enzyme	P80404	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192749	Proto-oncogene tyrosine-protein kinase Src	Enzyme	P12931	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0008246	Malonic acid	Acetic acid	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Malonyl-coa decarboxylase deficiency	Increased	Association	Human Blood	HMDB	24613099
Malonyl-coa decarboxylase deficiency	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	24613099
Malonyl-coa decarboxylase deficiency		Association	Human Urine	HMDB	3709568
Malonyl-coa decarboxylase deficiency		Association	Human Urine	HMDB	9177981
Malonyl-coa decarboxylase deficiency		Association	Human Urine	HMDB	7609455
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	7	Human feces	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	74	Human ; Human feces; Human sputum	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	33	Human stool; Human ; Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	2	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Food			FooDB	31437929
Plant	Fruit	Citrus sinensis	FooDB	31437929
Plant	Leaves	Musa x paradisiaca	FooDB	31437929
Plant		Apium graveolens	FooDB	31437929
Plant	Root	Beta vulgaris var. rubra	FooDB	31437929
Plant	Fruit	Citrus aurantiifolia	FooDB	31437929
Plant	Fruit	Phaseolus vulgaris	FooDB	31437929
Plant	Fruit	Citrus reticulata	FooDB	31437929
Plant	Root	Apium graveolens	FooDB	31437929
Plant		Beta vulgaris	FooDB	31437929
Plant	Leaves	Capsicum annuum var. annuum	FooDB	31437929
Plant	Leaves	Cucumis melo	FooDB	31437929
Plant	Fruit	Ficus carica	FooDB	31437929
Plant	Fruit	Prunus persica	FooDB	31437929
Plant	Leaves	Helianthus annuus	FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929
Plant		Phaseolus coccineus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified			2.1	5.5	uM	Adult (>18 years old)	Both	Combined malonic and methylmalonic aciduria	HMDB	21841779
Human Urine	Detected and Quantified			2.900	17.900	umol/mmol creatinine	Adult (>18 years old)	Both	Combined malonic and methylmalonic aciduria	HMDB	21841779
Human Blood	Detected and Quantified	16.8	6.7			uM	Adult (>18 years old)	Female	Early preeclampsia	HMDB	22494326
Human Blood	Detected and Quantified	40				uM	Adolescent (13-18 years old)	Female	Malonyl-Coa decarboxylase deficiency	HMDB	24613099
Human Cerebrospinal fluid (csf)	Detected and Quantified	180				uM	Adolescent (13-18 years old)	Female	Malonyl-Coa decarboxylase deficiency	HMDB	24613099
Human Urine	Detected and Quantified	690				umol/mmol creatinine	Infant (0-1 year old)	Male	Malonyl-Coa decarboxylase deficiency	HMDB	3709568
Human Urine	Detected and Quantified			21	890	umol/mmol creatinine	Children (1-13 years old)	Male	Malonyl-CoA decarboxylase deficiency	HMDB	9177981
Human Urine	Detected and Quantified			2170.752	5438.186	umol/mmol creatinine	Infant (0-1 year old)	Male	Malonyl-Coa decarboxylase deficiency	HMDB	7609455
Human Blood	Detected and Quantified	11.11	3			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Blood	Detected and Quantified	15.0	8.5			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23535240
Human Blood	Detected and Quantified	15.8	9.7			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23313728
Human Blood	Detected and Quantified	18.9	9.8			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	22494326
Human Urine	Detected and Quantified	0.6				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	21388201
Human Cerebrospinal fluid (csf)	Detected and Quantified	4.5				uM	Adolescent (13-18 years old)	Female	Normal	HMDB	24613099
Human Blood	Detected and Quantified	14.2				uM	Adolescent (13-18 years old)	Female	Normal	HMDB	24613099
Human Blood	Detected and Quantified	<0.89				uM	Adult (>18 years old)	Not Specified	Normal	HMDB	21841779
Human Urine	Detected and Quantified			0.8	1.1	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.8	1.5	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Blood	Detected and Quantified	13.5	1.2			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	15.0	0.58			uM	Adult (>18 years old)	Both	Normal	HMDB	19403942
Human Urine	Detected and Quantified	2.3		1.2	3.1	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	2.9		2.0	3.5	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	4.98	0.31			uM	Adult (>18 years old)	Both	Normal	HMDB	16139832
Human Urine	Detected and Quantified	54.96	113.059			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	58.315	82.251			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	13.366	10.276			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	15.041	13.798			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Saliva	Detected and Quantified	0.369	0.217			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.396	0.159			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.504	0.177			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.865	0.291			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Blood	Detected and Quantified			12.3	15.6	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	18052033
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	18085514
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	19573517
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27065191
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	25985090
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000691

DrugBank ID

DB02175

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Malonic_acid

METLIN ID

3237

PubChem Compound

867

PDB ID

Not Available

ChEBI ID

30794

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Pollitt RJ, Fowler B, Sardharwalla IB, Edwards MA, Gray RG: Increased excretion of propan-1,3-diol and 3-hydroxypropionic acid apparently caused by abnormal bacterial metabolism in the gut. Clin Chim Acta. 1987 Nov 16;169(2-3):151-7. doi: 10.1016/0009-8981(87)90314-7. [PubMed:3427776 ]
Haan EA, Scholem RD, Croll HB, Brown GK: Malonyl coenzyme A decarboxylase deficiency. Clinical and biochemical findings in a second child with a more severe enzyme defect. Eur J Pediatr. 1986 Apr;144(6):567-70. doi: 10.1007/BF00496037. [PubMed:3709568 ]
Yano S, Sweetman L, Thorburn DR, Mofidi S, Williams JC: A new case of malonyl coenzyme A decarboxylase deficiency presenting with cardiomyopathy. Eur J Pediatr. 1997 May;156(5):382-3. doi: 10.1007/s004310050619. [PubMed:9177981 ]
Buyukgebiz B, Jakobs C, Scholte HR, Huijmans JG, Kleijer WJ: Fatal neonatal malonic aciduria. J Inherit Metab Dis. 1998 Feb;21(1):76-7. doi: 10.1023/a:1005371616609. [PubMed:9501274 ]
Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. doi: 10.1016/s1570-0232(03)00277-0. [PubMed:12829005 ]
Belgorodsky B, Fadeev L, Ittah V, Benyamini H, Zelner S, Huppert D, Kotlyar AB, Gozin M: Formation and characterization of stable human serum albumin-tris-malonic acid [C60]fullerene complex. Bioconjug Chem. 2005 Sep-Oct;16(5):1058-62. doi: 10.1021/bc050103c. [PubMed:16173780 ]
Honda A, Yamashita K, Ikegami T, Hara T, Miyazaki T, Hirayama T, Numazawa M, Matsuzaki Y: Highly sensitive quantification of serum malonate, a possible marker for de novo lipogenesis, by LC-ESI-MS/MS. J Lipid Res. 2009 Oct;50(10):2124-30. doi: 10.1194/jlr.D800054-JLR200. Epub 2009 Apr 29. [PubMed:19403942 ]

Showing metabocard for Malonic acid (MMDBc0000138)

MOL for #<Metabolite:0x00007f46b95f19d0>

3D MOL for #<Metabolite:0x00007f46b95f19d0>

3D SDF for #<Metabolite:0x00007f46b95f19d0>

3D-SDF for #<Metabolite:0x00007f46b95f19d0>

PDB for #<Metabolite:0x00007f46b95f19d0>

3D PDB for #<Metabolite:0x00007f46b95f19d0>

SMILES for #<Metabolite:0x00007f46b95f19d0>

INCHI for #<Metabolite:0x00007f46b95f19d0>

Structure for #<Metabolite:0x00007f46b95f19d0>

3D Structure for #<Metabolite:0x00007f46b95f19d0>