Malonic acid

Identification

Name
Malonic acid
Accession Number
DB02175  (EXPT02179)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • Malonate
  • Propanedioic acid
External IDs
NSC-8124
Categories
UNII
9KX7ZMG0MK
CAS number
141-82-2
Weight
Average: 104.0615
Monoisotopic: 104.010958616
Chemical Formula
C3H4O4
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAspartate 1-decarboxylaseNot AvailableShigella flexneri
UProto-oncogene tyrosine-protein kinase SrcNot AvailableHuman
USigma factor SigB regulation protein RsbQNot AvailableBacillus subtilis (strain 168)
UPutative cytochrome P450Not AvailableStreptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
UU1 small nuclear ribonucleoprotein ANot AvailableHuman
UMalonamidase E2Not AvailableBradyrhizobium japonicum
UAcetyl transferaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
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
Fatty Acid BiosynthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00691
KEGG Compound
C04025
PubChem Compound
867
PubChem Substance
46504875
ChemSpider
844
BindingDB
14673
ChEBI
30794
ChEMBL
CHEMBL7942
HET
MLA
Wikipedia
Malonic_acid
PDB Entries
1e7p / 1nu4 / 1o4m / 1o9p / 1obl / 1ocl / 1pqh / 1q44 / 1rd5 / 1s0y
show 120 more

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 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

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-MSsplash10-0002-1900000000-a1463432c138c328557d
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0900000000-5e58241137fee0ccc64a
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-006t-9700000000-54976b3ce8f36ce0676d
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-001i-4930000000-e7dbed4919870db8dabf
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-05gl-1943000000-456e387fdf365bf0f8ee
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-6c56a402111059603ba4
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-f239df8fdd12e9a74445
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-6865e83f0df5c9831619
GC-MS Spectrum - EI-BGC-MSsplash10-0002-0900000000-a768f0aae86e17a3a6ba
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1900000000-a1463432c138c328557d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-5e58241137fee0ccc64a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-006t-9700000000-54976b3ce8f36ce0676d
GC-MS Spectrum - GC-MSGC-MSsplash10-05gl-1943000000-456e387fdf365bf0f8ee
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-4930000000-e7dbed4919870db8dabf
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-a45cfb1e2683f8ad8c5c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0911000000-8b0d7393c5dc4462a756
Mass Spectrum (Electron Ionization)MSsplash10-01ox-9000000000-dd4efef191376724d0f1
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-0a4i-9100000000-c7a1704f8a38ca2d245a
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0a4l-9100000000-9fa84f43f2e19b56035c
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-052f-9100000000-8a21753b343cf5dabdcb
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-0006-9000000000-6c56a402111059603ba4
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-0006-9000000000-f239df8fdd12e9a74445
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0udi-3900000000-e0a4c7e792cfd0e60cc3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0a4i-9000000000-4c03aa889e6a98ab532f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0a4l-9000000000-b3d14c986f292bdcf477
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-8e1041322f9acda4088a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-af4dccf21d68110099a1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-3900000000-e0a4c7e792cfd0e60cc3
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-4c03aa889e6a98ab532f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4l-9000000000-b3d14c986f292bdcf477
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-8e1041322f9acda4088a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-af4dccf21d68110099a1
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0006-3900000000-2126168f67ddb43e544d
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-9000000000-e9d5906655e37a471b89
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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
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
alpha,omega-dicarboxylic acid (CHEBI:30794) / Dicarboxylic acids (LMFA01170041)

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
Uniprot Name
Aspartate 1-decarboxylase
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 recept...
Gene Name
SRC
Uniprot ID
P12931
Uniprot Name
Proto-oncogene tyrosine-protein kinase Src
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
Uniprot Name
Sigma factor SigB regulation protein RsbQ
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 bi...
Gene Name
cyp158a2
Uniprot ID
Q9FCA6
Uniprot Name
Biflaviolin synthase CYP158A2
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 wit...
Gene Name
SNRPA
Uniprot ID
P09012
Uniprot Name
U1 small nuclear ribonucleoprotein A
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
Uniprot Name
Malonamidase E2
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
Uniprot Name
Acetyl transferase
Molecular Weight
20605.37 Da

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:10