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Identification
NameMalonic acid
Accession NumberDB02175  (EXPT02179)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
Malonate
Propanedioic acid
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII9KX7ZMG0MK
CAS number141-82-2
WeightAverage: 104.0615
Monoisotopic: 104.010958616
Chemical FormulaC3H4O4
InChI KeyInChIKey=OFOBLEOULBTSOW-UHFFFAOYSA-N
InChI
InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
IUPAC Name
propanedioic acid
SMILES
OC(=O)CC(O)=O
Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Fatty Acid BiosynthesisMetabolicSMP00456
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.519
Blood Brain Barrier+0.8916
Caco-2 permeable-0.6955
P-glycoprotein substrateNon-substrate0.7759
P-glycoprotein inhibitor INon-inhibitor0.9816
P-glycoprotein inhibitor IINon-inhibitor0.9822
Renal organic cation transporterNon-inhibitor0.9644
CYP450 2C9 substrateNon-substrate0.843
CYP450 2D6 substrateNon-substrate0.9152
CYP450 3A4 substrateNon-substrate0.8043
CYP450 1A2 substrateNon-inhibitor0.9553
CYP450 2C9 inhibitorNon-inhibitor0.9715
CYP450 2D6 inhibitorNon-inhibitor0.9554
CYP450 2C19 inhibitorNon-inhibitor0.973
CYP450 3A4 inhibitorNon-inhibitor0.8814
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9905
Ames testNon AMES toxic0.9393
CarcinogenicityNon-carcinogens0.6247
BiodegradationReady biodegradable0.8663
Rat acute toxicity1.8686 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9795
hERG inhibition (predictor II)Non-inhibitor0.9857
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point135 dec °CPhysProp
water solubility7.63E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.81HANSCH,C ET AL. (1995)
pKa2.85 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility197.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity18.99 m3·mol-1ChemAxon
Polarizability8.13 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-1900000000-a1463432c138c328557dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0900000000-5e58241137fee0ccc64aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-9700000000-54976b3ce8f36ce0676dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4930000000-e7dbed4919870db8dabfView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-05gl-1943000000-456e387fdf365bf0f8eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9100000000-c7a1704f8a38ca2d245aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4l-9100000000-9fa84f43f2e19b56035cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052f-9100000000-8a21753b343cf5dabdcbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9000000000-6c56a402111059603ba4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-f239df8fdd12e9a74445View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-3900000000-e0a4c7e792cfd0e60cc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-4c03aa889e6a98ab532fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-9000000000-b3d14c986f292bdcf477View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-8e1041322f9acda4088aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-af4dccf21d68110099a1View in MoNA
MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-dd4efef191376724d0f1View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Michinori Kuraya, “Process for producing acrylic rubber by copolymerizing acrylic ester and malonic acid derivative having active methylene group.” U.S. Patent US4154914, issued June, 1963.

US4154914
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Shigella flexneri
Pharmacological action
unknown
General Function:
Aspartate 1-decarboxylase activity
Specific Function:
Catalyzes the pyruvoyl-dependent decarboxylation of aspartate to produce beta-alanine.
Gene Name:
panD
Uniprot ID:
P0A793
Molecular Weight:
13833.595 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sh3/sh2 adaptor activity
Specific Function:
Non-receptor protein tyrosine kinase which is activated following engagement of many different classes of cellular receptors including immune response receptors, integrins and other adhesion receptors, receptor protein tyrosine kinases, G protein-coupled receptors as well as cytokine receptors. Participates in signaling pathways that control a diverse spectrum of biological activities including...
Gene Name:
SRC
Uniprot ID:
P12931
Molecular Weight:
59834.295 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 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
Positive regulator required for energy stress activation of the sigma-B transcription factor. Could be required for RsbP phosphatase activity.
Gene Name:
rsbQ
Uniprot ID:
O07015
Molecular Weight:
30019.91 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 ]
Kind
Protein
Organism
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Pharmacological action
unknown
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific Function:
Catalyze oxidative C-C coupling reaction to polymerize flaviolin and form highly conjugated pigments which protect the soil bacterium from deleterious effects of UV irradiation (three isomers of biflaviolin and one triflaviolin).
Gene Name:
cyp158a2
Uniprot ID:
Q9FCA6
Molecular Weight:
44354.085 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
U1 snrna binding
Specific Function:
Component of the spliceosomal U1 snRNP, which is essential for recognition of the pre-mRNA 5' splice-site and the subsequent assembly of the spliceosome. U1 snRNP is the first snRNP to interact with pre-mRNA. This interaction is required for the subsequent binding of U2 snRNP and the U4/U6/U5 tri-snRNP. SNRPA binds stem loop II of U1 snRNA. In a snRNP-free form (SF-A) may be involved in coupled...
Gene Name:
SNRPA
Uniprot ID:
P09012
Molecular Weight:
31279.365 Da
Kind
Protein
Organism
Bradyrhizobium japonicum
Pharmacological action
unknown
General Function:
Carbon-nitrogen ligase activity, with glutamine as amido-n-donor
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q9ZIV5
Molecular Weight:
43681.365 Da
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
unknown
General Function:
N-acetyltransferase activity
Specific Function:
Not Available
Gene Name:
rimL
Uniprot ID:
Q8ZPC0
Molecular Weight:
20605.37 Da
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17