Showing Compound Card for Malonic acid (CDB000280)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:28:39 UTC
Updated at2020-12-07 19:07:19 UTC
CannabisDB IDCDB000280
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMalonic acid
DescriptionMalonic 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 two carboxylic acid groups. Malonic acid is a very hydrophobic molecule, practically insoluble in water. Malonic acid exists in all living species, ranging from bacteria to humans. In humans, malonic acid is involved in fatty acid biosynthesis. Malonic acid has also been detected, but not quantified, in several different foods, such as red beetroots, corns, scarlet beans, common beets, and cow milks. Malonic acid is also one of several organic acids that are known to occur in cannabis plants (PMID: 6991645 ). Industrially, it is used in a number of manufacturing processes as a high value specialty chemical, including the electronics industry, flavors and fragrances industry, specialty solvents, polymer crosslinking, and pharmaceutical industry.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
H2MaloChEBI
HOOC-CH2-COOHChEBI
Propanedioic acidChEBI
PropanedioateGenerator
MalonateGenerator
alpha,Omega-dicarboxylic acidHMDB
Carboxyacetic acidHMDB
DicarboxylateHMDB
Dicarboxylic acidHMDB
DicarboxymethaneHMDB
Kyselina malonovaHMDB
Malonate dicarboxylic acidHMDB
Metahnedicarboxylic acidHMDB
Methanedicarbonic acidHMDB
Methanedicarboxylic acidHMDB
Propanedioic acid dithallium saltHMDB
Propanediolic acidHMDB
Thallium malonateHMDB
Malonic acid, 2-(14)C-labeledHMDB
Malonic acid, monocalcium saltHMDB
Malonic acid, 1,3-(14)C2-labeledHMDB
Malonic acid, diammonium saltHMDB
Malonic acid, disodium saltHMDB
Malonic acid, dithallium saltHMDB
Malonic acid, dipotassium saltHMDB
Malonic acid, disodium salt, 1-(14)C-labeledHMDB
Malonic acid, monosodium saltHMDB
Malonic acid, potassium saltHMDB
Malonic acid, sodium saltHMDB
Thallous malonateHMDB
Dithallium malonateHMDB
Monosodium malonateHMDB
Malonic acidGenerator
Chemical FormulaC3H4O4
Average Molecular Weight104.06
Monoisotopic Molecular Weight104.011
IUPAC Namepropanedioic acid
Traditional Namemalonic acid
CAS Registry Number141-82-2
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 KeyOFOBLEOULBTSOW-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility763 mg/mLNot Available
logP-0.81HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.6ALOGPS
logP-0.33ChemAxon
logS0.28ALOGPS
pKa (Strongest Acidic)2.43ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity18.99 m³·mol⁻¹ChemAxon
Polarizability8.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-dd4efef191376724d0f12015-03-01View Spectrum
GC-MSMalonic acid, 2 TMS, GC-MS Spectrumsplash10-0002-1900000000-a1463432c138c328557dSpectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-5e58241137fee0ccc64aSpectrum
GC-MSMalonic acid, 2 TMS, GC-MS Spectrumsplash10-006t-9700000000-54976b3ce8f36ce0676dSpectrum
GC-MSMalonic acid, 2 TMS, GC-MS Spectrumsplash10-001i-4930000000-e7dbed4919870db8dabfSpectrum
GC-MSMalonic acid, 3 TMS, GC-MS Spectrumsplash10-05gl-1943000000-456e387fdf365bf0f8eeSpectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-6c56a402111059603ba4Spectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-f239df8fdd12e9a74445Spectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-6865e83f0df5c9831619Spectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-a768f0aae86e17a3a6baSpectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1900000000-a1463432c138c328557dSpectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-5e58241137fee0ccc64aSpectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-006t-9700000000-54976b3ce8f36ce0676dSpectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-05gl-1943000000-456e387fdf365bf0f8eeSpectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-001i-4930000000-e7dbed4919870db8dabfSpectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-a45cfb1e2683f8ad8c5cSpectrum
GC-MSMalonic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0911000000-8b0d7393c5dc4462a756Spectrum
Predicted GC-MSMalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zfu-9300000000-cbc239877c485e6dff65Spectrum
Predicted GC-MSMalonic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9410000000-c30e36ba8e95ef1c83beSpectrum
Predicted GC-MSMalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalonic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalonic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalonic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9100000000-c7a1704f8a38ca2d245a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4l-9100000000-9fa84f43f2e19b56035c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052f-9100000000-8a21753b343cf5dabdcb2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9000000000-6c56a402111059603ba42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-f239df8fdd12e9a744452012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-3900000000-e0a4c7e792cfd0e60cc32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-4c03aa889e6a98ab532f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-9000000000-b3d14c986f292bdcf4772012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-8e1041322f9acda4088a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-af4dccf21d68110099a12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-3900000000-e0a4c7e792cfd0e60cc32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-4c03aa889e6a98ab532f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-b3d14c986f292bdcf4772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-8e1041322f9acda4088a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-af4dccf21d68110099a12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-3900000000-2126168f67ddb43e544d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9000000000-e9d5906655e37a471b892017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c742107695804ea678f12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-cb15cb8d630a4fbd07502021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-7900000000-795ca313c7daaf448ede2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-9400000000-a6390568ef61fe1a284e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9100000000-cc17364c6d52c2c208f32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-6900000000-b1169abf90c9693f8e302016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-cec6a47ea3eb4a95a9572016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-cffa3dea7855764ea8542016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
4-aminobutyrate aminotransferase, mitochondrialABAT16p13.2P80404 details
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
Proto-oncogene tyrosine-protein kinase SrcSRC20q12-q13P12931 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000691
DrugBank IDDB02175
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008117
KNApSAcK IDC00001193
Chemspider ID844
KEGG Compound IDC04025
BioCyc IDMALONATE
BiGG IDNot Available
Wikipedia LinkMalonic_acid
METLIN ID3237
PubChem Compound867
PDB IDNot Available
ChEBI ID30794
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Enzymes

Enzyme Details
1. 4-aminobutyrate aminotransferase, mitochondrial
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:
ABAT
Uniprot ID:
P80404
Molecular weight:
56438.405
Enzyme Details
2. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Enzyme Details
3. Proto-oncogene tyrosine-protein kinase Src
General function:
Involved in protein kinase activity
Specific function:
ATP + a [protein]-L-tyrosine = ADP + a [protein]-L-tyrosine phosphate
Gene Name:
SRC
Uniprot ID:
P12931
Molecular weight:
59834.3