Methylmalonic Acid

Identification

Name
Methylmalonic Acid
Accession Number
DB04183  (EXPT01309)
Type
Small Molecule
Groups
Experimental
Description

A malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA. [PubChem]

Structure
Thumb
Synonyms
Not Available
External IDs
NSC-25201
Product Ingredients
Not Available
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
Not Available
Categories
UNII
8LL8S712J7
CAS number
516-05-2
Weight
Average: 118.088
Monoisotopic: 118.02660868
Chemical Formula
C4H6O4
InChI Key
ZIYVHBGGAOATLY-UHFFFAOYSA-N
InChI
InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)
IUPAC Name
2-methylpropanedioic acid
SMILES
CC(C(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMethylmalonyl-CoA carboxyltransferase 12S subunitNot AvailablePropionibacterium freudenreichii subsp. shermanii
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDisease
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDisease
3-hydroxyisobutyric acid dehydrogenase deficiencyDisease
3-hydroxyisobutyric aciduriaDisease
Propanoate MetabolismMetabolic
Valine, Leucine and Isoleucine DegradationMetabolic
Beta-Ketothiolase DeficiencyDisease
Malonic AciduriaDisease
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDisease
3-Methylglutaconic Aciduria Type IDisease
3-Methylglutaconic Aciduria Type IVDisease
Maple Syrup Urine DiseaseDisease
Methylmalonic Aciduria Due to Cobalamin-Related DisordersDisease
Propionic AcidemiaDisease
Vitamin K MetabolismMetabolic
3-Methylglutaconic Aciduria Type IIIDisease
Methylmalonic AciduriaDisease
Isovaleric AciduriaDisease
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDisease
Malonyl-coa decarboxylase deficiencyDisease
Isobutyryl-coa dehydrogenase deficiencyDisease
Isovaleric acidemiaDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
Human Metabolome Database
HMDB00202
KEGG Compound
C02170
PubChem Compound
487
PubChem Substance
46506625
ChemSpider
473
BindingDB
50038341
ChEBI
30860
ChEMBL
CHEMBL1232416
HET
DXX
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)135 dec °CPhysProp
water solubility6.79E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
pKa3.12 (at 20 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility149.0 mg/mLALOGPS
logP0.17ALOGPS
logP0.21ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)2.48ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.56 m3·mol-1ChemAxon
Polarizability10.06 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7625
Blood Brain Barrier+0.8895
Caco-2 permeable-0.729
P-glycoprotein substrateNon-substrate0.7594
P-glycoprotein inhibitor INon-inhibitor0.9881
P-glycoprotein inhibitor IINon-inhibitor0.9846
Renal organic cation transporterNon-inhibitor0.9626
CYP450 2C9 substrateNon-substrate0.7899
CYP450 2D6 substrateNon-substrate0.9288
CYP450 3A4 substrateNon-substrate0.7995
CYP450 1A2 substrateNon-inhibitor0.9597
CYP450 2C9 inhibitorNon-inhibitor0.9173
CYP450 2D6 inhibitorNon-inhibitor0.9599
CYP450 2C19 inhibitorNon-inhibitor0.9771
CYP450 3A4 inhibitorNon-inhibitor0.9291
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9908
Ames testNon AMES toxic0.9636
CarcinogenicityNon-carcinogens0.52
BiodegradationReady biodegradable0.8312
Rat acute toxicity1.8620 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9857
hERG inhibition (predictor II)Non-inhibitor0.9879
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0002-1910000000-cf95dd8a481761a28664
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-006t-8900000000-4d8795e7e4300cc7ceff
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00lr-5940000000-56b86ada220d335ce30a
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-001i-9301000000-54e5247d046de566ac1e
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-004i-9000000000-b9ee59dddf90dfc7c461
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1910000000-cf95dd8a481761a28664
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-006t-8900000000-4d8795e7e4300cc7ceff
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-9301000000-54e5247d046de566ac1e
GC-MS Spectrum - GC-MSGC-MSsplash10-00lr-5940000000-56b86ada220d335ce30a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-684a11ce99cccbd9194a
LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)LC-MS/MSsplash10-00di-9000000000-1578bea9a6b8b12e2f9b
LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)LC-MS/MSsplash10-05fr-9000000000-0e443f81ee9c6c9b1fa5
LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)LC-MS/MSsplash10-0ab9-9100000000-d23d6a0a35141ed9a950
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-01b9-6900000000-6d969044a89f00e1b46f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00di-9000000000-0f655174050263224e67
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0ab9-9000000000-26a654fb133b28a816a0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4i-9000000000-7afd566e443d5fa38887
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0a4i-9000000000-5c4795e954d5c3e9b74e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-01b9-6900000000-6d969044a89f00e1b46f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9000000000-0f655174050263224e67
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0ab9-9000000000-26a654fb133b28a816a0
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-7afd566e443d5fa38887
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-5c4795e954d5c3e9b74e
Predicted LC-MS/MS Spectrum - 10V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 10V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, NegativePredicted LC-MS/MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-05di-9000000000-8d09b408489f7b1743b5
1H NMR Spectrum1D NMRNot applicable
13C NMR Spectrum1D NMRNot applicable
1H NMR Spectrum1D NMRNot applicable
13C NMR Spectrum1D NMRNot applicable
1H NMR Spectrum1D NMRNot applicable
13C NMR Spectrum1D NMRNot applicable
[1H,13C] 2D NMR Spectrum2D NMRNot applicable

Taxonomy

Description
This compound belongs to the class of chemical entities known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Organic acids and derivatives
Sub Class
Carboxylic acids and derivatives
Direct Parent
Dicarboxylic acids and derivatives
Alternative Parents
1,3-dicarbonyl compounds / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
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
C4-dicarboxylic acid (CHEBI:30860 ) / Dicarboxylic acids (LMFA01170118 )

Targets

Kind
Protein
Organism
Propionibacterium freudenreichii subsp. shermanii
Pharmacological action
Unknown
General Function
Methylmalonyl-coa carboxytransferase activity
Specific Function
The 12S subunit specifically catalyzes the transfer of the carboxyl group of methylmalonyl CoA to the biotin of the 1.3S subunit forming propanoyl-CoA and carboxylated 1.3S-biotin.
Gene Name
Not Available
Uniprot ID
Q8GBW6
Uniprot Name
Methylmalonyl-CoA carboxyltransferase 12S subunit
Molecular Weight
65926.0 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Drug created on June 13, 2005 07:24 / Updated on September 01, 2017 11:14