Identification
- Generic Name
- D-Malic acid
- DrugBank Accession Number
- DB03499
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for D-Malic acid (DB03499)
- Weight
- Average: 134.0874
Monoisotopic: 134.021523302 - Chemical Formula
- C4H6O5
- Synonyms
- (+)-D-malic acid
- (R)-2-hydroxybutanedioic acid
- (R)-malic acid
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism UNAD-dependent malic enzyme, mitochondrial Not Available Humans UCitrate synthase, mitochondrial Not Available Humans UCircadian clock protein KaiB Not Available Synechocystis sp. (strain PCC 6803 / Kazusa) UFumarate hydratase class II Not Available Escherichia coli (strain K12) UMalate synthase G Not Available Mycobacterium tuberculosis UCapsule biosynthesis protein Not Available Neisseria meningitidis - 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
- Not Available
- 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
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Hydroxy acids and derivatives
- Sub Class
- Beta hydroxy acids and derivatives
- Direct Parent
- Beta hydroxy acids and derivatives
- Alternative Parents
- Short-chain hydroxy acids and derivatives / Fatty acids and conjugates / Dicarboxylic acids and derivatives / Alpha hydroxy acids and derivatives / Secondary alcohols / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alcohol / Aliphatic acyclic compound / Alpha-hydroxy acid / Beta-hydroxy acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Fatty acid / Hydrocarbon derivative
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- malic acid (CHEBI:30796)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- P750Y95K96
- CAS number
- 636-61-3
- InChI Key
- BJEPYKJPYRNKOW-UWTATZPHSA-N
- InChI
- InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1
- IUPAC Name
- (2R)-2-hydroxybutanedioic acid
- SMILES
- O[C@H](CC(O)=O)C(O)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0031518
- KEGG Compound
- C00497
- PubChem Compound
- 92824
- PubChem Substance
- 46504723
- ChemSpider
- 83793
- ChEBI
- 30796
- ChEMBL
- CHEMBL225986
- ZINC
- ZINC000000895264
- PDBe Ligand
- MLT
- PDB Entries
- 1amz / 1c1e / 1fuo / 1fup / 1fur / 1kq7 / 1n8w / 1nbe / 1ouw / 1pj4 … show 136 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 218.0 mg/mL ALOGPS logP -0.87 ALOGPS logP -1.1 Chemaxon logS 0.21 ALOGPS pKa (Strongest Acidic) 3.2 Chemaxon pKa (Strongest Basic) -3.9 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 94.83 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 24.88 m3·mol-1 Chemaxon Polarizability 10.93 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 - 0.9026 Blood Brain Barrier + 0.8643 Caco-2 permeable - 0.777 P-glycoprotein substrate Non-substrate 0.7629 P-glycoprotein inhibitor I Non-inhibitor 0.972 P-glycoprotein inhibitor II Non-inhibitor 0.9077 Renal organic cation transporter Non-inhibitor 0.9625 CYP450 2C9 substrate Non-substrate 0.8623 CYP450 2D6 substrate Non-substrate 0.899 CYP450 3A4 substrate Non-substrate 0.7606 CYP450 1A2 substrate Non-inhibitor 0.9444 CYP450 2C9 inhibitor Non-inhibitor 0.9476 CYP450 2D6 inhibitor Non-inhibitor 0.9435 CYP450 2C19 inhibitor Non-inhibitor 0.9515 CYP450 3A4 inhibitor Non-inhibitor 0.9153 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9863 Ames test Non AMES toxic 0.881 Carcinogenicity Non-carcinogens 0.6985 Biodegradation Ready biodegradable 0.9763 Rat acute toxicity 1.6882 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9842 hERG inhibition (predictor II) Non-inhibitor 0.976
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 122.2689017 predictedDarkChem Lite v0.1.0 [M-H]- 122.2889017 predictedDarkChem Lite v0.1.0 [M-H]- 122.4619017 predictedDarkChem Lite v0.1.0 [M-H]- 118.559814 predictedDeepCCS 1.0 (2019) [M+H]+ 123.7469017 predictedDarkChem Lite v0.1.0 [M+H]+ 123.2220017 predictedDarkChem Lite v0.1.0 [M+H]+ 124.0264017 predictedDarkChem Lite v0.1.0 [M+H]+ 122.153595 predictedDeepCCS 1.0 (2019) [M+Na]+ 122.7776017 predictedDarkChem Lite v0.1.0 [M+Na]+ 122.9090017 predictedDarkChem Lite v0.1.0 [M+Na]+ 123.0190017 predictedDarkChem Lite v0.1.0 [M+Na]+ 130.86089 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Oxaloacetate decarboxylase activity
- Specific Function
- Not Available
- Gene Name
- ME2
- Uniprot ID
- P23368
- Uniprot Name
- NAD-dependent malic enzyme, mitochondrial
- Molecular Weight
- 65442.945 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Poly(a) rna binding
- Specific Function
- Not Available
- Gene Name
- CS
- Uniprot ID
- O75390
- Uniprot Name
- Citrate synthase, mitochondrial
- Molecular Weight
- 51712.025 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
- Synechocystis sp. (strain PCC 6803 / Kazusa)
- Pharmacological action
- Unknown
- General Function
- Identical protein binding
- Specific Function
- Component of the KaiABC clock protein complex, which constitutes the main circadian regulator in cyanobacteria. The KaiABC complex may act as a promoter-non-specific transcription regulator that re...
- Gene Name
- kaiB
- Uniprot ID
- P74645
- Uniprot Name
- Circadian clock protein KaiB
- Molecular Weight
- 11934.89 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Fumarate hydratase activity
- Specific Function
- Catalyzes the reversible addition of water to fumarate to give L-malate.
- Gene Name
- fumC
- Uniprot ID
- P05042
- Uniprot Name
- Fumarate hydratase class II
- Molecular Weight
- 50488.44 Da
References
- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- Involved in the glycolate utilization. Catalyzes the condensation and subsequent hydrolysis of acetyl-coenzyme A (acetyl-CoA) and glyoxylate to form malate and CoA.
- Specific Function
- Coenzyme binding
- Gene Name
- glcB
- Uniprot ID
- P9WK17
- Uniprot Name
- Malate synthase G
- Molecular Weight
- 80402.24 Da
References
- Kind
- Protein
- Organism
- Neisseria meningitidis
- Pharmacological action
- Unknown
- General Function
- Metal ion binding
- Specific Function
- Not Available
- Gene Name
- synC
- Uniprot ID
- Q57265
- Uniprot Name
- Capsule biosynthesis protein
- Molecular Weight
- 38347.39 Da
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52