Malonic acid
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Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Malonic acid
- DrugBank Accession Number
- DB02175
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 104.0615
Monoisotopic: 104.010958616 - Chemical Formula
- C3H4O4
- Synonyms
- Propanedioic acid
- External IDs
- NSC-8124
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAspartate 1-decarboxylase Not Available Shigella flexneri UProto-oncogene tyrosine-protein kinase Src Not Available Humans USigma factor SigB regulation protein RsbQ Not Available Bacillus subtilis (strain 168) UBiflaviolin synthase CYP158A2 Not Available Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145) UU1 small nuclear ribonucleoprotein A Not Available Humans UMalonamidase E2 Not Available Bradyrhizobium japonicum UAcetyl transferase Not Available Salmonella 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
Pathway Category Fatty Acid Biosynthesis Metabolic - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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 / Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Dicarboxylic acid or derivatives / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- alpha,omega-dicarboxylic acid (CHEBI:30794) / Dicarboxylic acids (LMFA01170041)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9KX7ZMG0MK
- CAS number
- 141-82-2
- 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
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
- HMDB0000691
- KEGG Compound
- C04025
- PubChem Compound
- 867
- PubChem Substance
- 46504875
- ChemSpider
- 844
- BindingDB
- 14673
- ChEBI
- 30794
- ChEMBL
- CHEMBL7942
- ZINC
- ZINC000000895212
- PDBe Ligand
- MLA
- Wikipedia
- Malonic_acid
- PDB Entries
- 1e7p / 1nu4 / 1o4m / 1o9p / 1obl / 1ocl / 1pqh / 1q44 / 1rd5 / 1s0y … show 212 more
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 135 dec °C PhysProp water solubility 7.63E+005 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -0.81 HANSCH,C ET AL. (1995) pKa 2.85 (at 25 °C) KORTUM,G ET AL (1961) - Predicted Properties
Property Value Source Water Solubility 197.0 mg/mL 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 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.519 Blood Brain Barrier + 0.8916 Caco-2 permeable - 0.6955 P-glycoprotein substrate Non-substrate 0.7759 P-glycoprotein inhibitor I Non-inhibitor 0.9816 P-glycoprotein inhibitor II Non-inhibitor 0.9822 Renal organic cation transporter Non-inhibitor 0.9644 CYP450 2C9 substrate Non-substrate 0.843 CYP450 2D6 substrate Non-substrate 0.9152 CYP450 3A4 substrate Non-substrate 0.8043 CYP450 1A2 substrate Non-inhibitor 0.9553 CYP450 2C9 inhibitor Non-inhibitor 0.9715 CYP450 2D6 inhibitor Non-inhibitor 0.9554 CYP450 2C19 inhibitor Non-inhibitor 0.973 CYP450 3A4 inhibitor Non-inhibitor 0.8814 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9905 Ames test Non AMES toxic 0.9393 Carcinogenicity Non-carcinogens 0.6247 Biodegradation Ready biodegradable 0.8663 Rat acute toxicity 1.8686 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9795 hERG inhibition (predictor II) Non-inhibitor 0.9857
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 113.6359546 predictedDarkChem Lite v0.1.0 [M-H]- 113.5604546 predictedDarkChem Lite v0.1.0 [M-H]- 124.70938 predictedDeepCCS 1.0 (2019) [M-H]- 113.6359546 predictedDarkChem Lite v0.1.0 [M-H]- 113.5604546 predictedDarkChem Lite v0.1.0 [M-H]- 124.70938 predictedDeepCCS 1.0 (2019) [M+H]+ 127.47143 predictedDeepCCS 1.0 (2019) [M+H]+ 127.47143 predictedDeepCCS 1.0 (2019) [M+Na]+ 135.89366 predictedDeepCCS 1.0 (2019) [M+Na]+ 135.89366 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsAspartate 1-decarboxylase
- Kind
- Protein
- Organism
- Shigella flexneri
- Pharmacological action
- Unknown
- General Function
- Catalyzes the pyruvoyl-dependent decarboxylation of aspartate to produce beta-alanine.
- Specific Function
- aspartate 1-decarboxylase activity
- Gene Name
- panD
- Uniprot ID
- P0A793
- Uniprot Name
- Aspartate 1-decarboxylase
- Molecular Weight
- 13833.595 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 transcription, immune response, cell adhesion, cell cycle progression, apoptosis, migration, and transformation. Due to functional redundancy between members of the SRC kinase family, identification of the specific role of each SRC kinase is very difficult. SRC appears to be one of the primary kinases activated following engagement of receptors and plays a role in the activation of other protein tyrosine kinase (PTK) families. Receptor clustering or dimerization leads to recruitment of SRC to the receptor complexes where it phosphorylates the tyrosine residues within the receptor cytoplasmic domains. Plays an important role in the regulation of cytoskeletal organization through phosphorylation of specific substrates such as AFAP1. Phosphorylation of AFAP1 allows the SRC SH2 domain to bind AFAP1 and to localize to actin filaments. Cytoskeletal reorganization is also controlled through the phosphorylation of cortactin (CTTN) (Probable). When cells adhere via focal adhesions to the extracellular matrix, signals are transmitted by integrins into the cell resulting in tyrosine phosphorylation of a number of focal adhesion proteins, including PTK2/FAK1 and paxillin (PXN) (PubMed:21411625). In addition to phosphorylating focal adhesion proteins, SRC is also active at the sites of cell-cell contact adherens junctions and phosphorylates substrates such as beta-catenin (CTNNB1), delta-catenin (CTNND1), and plakoglobin (JUP). Another type of cell-cell junction, the gap junction, is also a target for SRC, which phosphorylates connexin-43 (GJA1). SRC is implicated in regulation of pre-mRNA-processing and phosphorylates RNA-binding proteins such as KHDRBS1 (Probable). Phosphorylates PKP3 at 'Tyr-195' in response to reactive oxygen species, which may cause the release of PKP3 from desmosome cell junctions into the cytoplasm (PubMed:25501895). Also plays a role in PDGF-mediated tyrosine phosphorylation of both STAT1 and STAT3, leading to increased DNA binding activity of these transcription factors (By similarity). Involved in the RAS pathway through phosphorylation of RASA1 and RASGRF1 (PubMed:11389730). Plays a role in EGF-mediated calcium-activated chloride channel activation (PubMed:18586953). Required for epidermal growth factor receptor (EGFR) internalization through phosphorylation of clathrin heavy chain (CLTC and CLTCL1) at 'Tyr-1477'. Involved in beta-arrestin (ARRB1 and ARRB2) desensitization through phosphorylation and activation of GRK2, leading to beta-arrestin phosphorylation and internalization. Has a critical role in the stimulation of the CDK20/MAPK3 mitogen-activated protein kinase cascade by epidermal growth factor (Probable). Might be involved not only in mediating the transduction of mitogenic signals at the level of the plasma membrane but also in controlling progression through the cell cycle via interaction with regulatory proteins in the nucleus (PubMed:7853507). Plays an important role in osteoclastic bone resorption in conjunction with PTK2B/PYK2. Both the formation of a SRC-PTK2B/PYK2 complex and SRC kinase activity are necessary for this function. Recruited to activated integrins by PTK2B/PYK2, thereby phosphorylating CBL, which in turn induces the activation and recruitment of phosphatidylinositol 3-kinase to the cell membrane in a signaling pathway that is critical for osteoclast function (PubMed:14585963, PubMed:8755529). Promotes energy production in osteoclasts by activating mitochondrial cytochrome C oxidase (PubMed:12615910). Phosphorylates DDR2 on tyrosine residues, thereby promoting its subsequent autophosphorylation (PubMed:16186108). Phosphorylates RUNX3 and COX2 on tyrosine residues, TNK2 on 'Tyr-284' and CBL on 'Tyr-731' (PubMed:20100835, PubMed:21309750). Enhances RIGI-elicited antiviral signaling (PubMed:19419966). Phosphorylates PDPK1 at 'Tyr-9', 'Tyr-373' and 'Tyr-376' (PubMed:14585963). Phosphorylates BCAR1 at 'Tyr-128' (PubMed:22710723). Phosphorylates CBLC at multiple tyrosine residues, phosphorylation at 'Tyr-341' activates CBLC E3 activity (PubMed:20525694). Phosphorylates synaptic vesicle protein synaptophysin (SYP) (By similarity). Involved in anchorage-independent cell growth (PubMed:19307596). Required for podosome formation (By similarity). Mediates IL6 signaling by activating YAP1-NOTCH pathway to induce inflammation-induced epithelial regeneration (PubMed:25731159). Phosphorylates OTUB1, promoting deubiquitination of RPTOR (PubMed:35927303). Phosphorylates caspase CASP8 at 'Tyr-380' which negatively regulates CASP8 processing and activation, down-regulating CASP8 proapoptotic function (PubMed:16619028)
- Specific Function
- ATP binding
- Gene Name
- SRC
- Uniprot ID
- P12931
- Uniprot Name
- Proto-oncogene tyrosine-protein kinase Src
- Molecular Weight
- 59834.295 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Bacillus subtilis (strain 168)
- Pharmacological action
- Unknown
- General Function
- Positive regulator required for energy stress activation of the sigma-B transcription factor. Could be required for RsbP phosphatase activity.
- Specific Function
- Not Available
- Gene Name
- rsbQ
- Uniprot ID
- O07015
- Uniprot Name
- Sigma factor SigB regulation protein RsbQ
- Molecular Weight
- 30019.91 Da
References
4. DetailsBiflaviolin synthase CYP158A2
- Kind
- Protein
- Organism
- Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
- Pharmacological action
- Unknown
- General Function
- Catalyzes 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).
- Specific Function
- heme binding
- Gene Name
- cyp158a2
- Uniprot ID
- Q9FCA6
- Uniprot Name
- Biflaviolin synthase CYP158A2
- Molecular Weight
- 44354.085 Da
5. DetailsU1 small nuclear ribonucleoprotein A
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 pre-mRNA splicing and polyadenylation process. May bind preferentially to the 5'-UGCAC-3' motif on RNAs
- Specific Function
- DNA binding
- Gene Name
- SNRPA
- Uniprot ID
- P09012
- Uniprot Name
- U1 small nuclear ribonucleoprotein A
- Molecular Weight
- 31279.365 Da
6. DetailsMalonamidase E2
- Kind
- Protein
- Organism
- Bradyrhizobium japonicum
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- catalytic activity
- Gene Name
- Not Available
- Uniprot ID
- Q9ZIV5
- Uniprot Name
- Malonamidase E2
- Molecular Weight
- 43681.365 Da
7. DetailsAcetyl transferase
- Kind
- Protein
- Organism
- Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- peptide-alanine-alpha-N-acetyltransferase activity
- Gene Name
- rimL
- Uniprot ID
- Q8ZPC0
- Uniprot Name
- Acetyl transferase
- Molecular Weight
- 20605.37 Da
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52