Acetoacetic acid
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Overview
- DrugBank ID
- DB01762
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
Identification
- Generic Name
- Acetoacetic acid
- DrugBank Accession Number
- DB01762
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 102.0886
Monoisotopic: 102.031694058 - Chemical Formula
- C4H6O3
- Synonyms
- 3-ketobutanoic acid
- 3-Ketobutyric acid
- 3-Oxobutanoic acid
- 3-Oxobutyric acid
- beta-Ketobutyric acid
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UFumarylacetoacetase Not Available Humans - 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
- 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 short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Keto acids and derivatives
- Sub Class
- Short-chain keto acids and derivatives
- Direct Parent
- Short-chain keto acids and derivatives
- Alternative Parents
- Beta-keto acids and derivatives / Beta-hydroxy ketones / 1,3-dicarbonyl compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1,3-dicarbonyl compound / Aliphatic acyclic compound / Beta-hydroxy ketone / Beta-keto acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Ketone / Monocarboxylic acid or derivatives
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- 3-oxo monocarboxylic acid, ketone body (CHEBI:15344) / Oxo fatty acids (C00164) / Oxo fatty acids (LMFA01060003)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 4ZI204Y1MC
- CAS number
- 541-50-4
- InChI Key
- WDJHALXBUFZDSR-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
- IUPAC Name
- 3-oxobutanoic acid
- SMILES
- CC(=O)CC(O)=O
References
- Synthesis Reference
Erik Herkenrath, "Process for the production of 1,2-dihydro-2-oxo-4-methyl-7-acetoacetic acid amido-quinoline." U.S. Patent US4064131, issued July, 1956.
US4064131- General References
- Martin PM, Gopal E, Ananth S, Zhuang L, Itagaki S, Prasad BM, Smith SB, Prasad PD, Ganapathy V: Identity of SMCT1 (SLC5A8) as a neuron-specific Na+-coupled transporter for active uptake of L-lactate and ketone bodies in the brain. J Neurochem. 2006 Jul;98(1):279-88. [Article]
- External Links
- Human Metabolome Database
- HMDB0000060
- KEGG Compound
- C00164
- PubChem Compound
- 96
- PubChem Substance
- 46505003
- ChemSpider
- 94
- ChEBI
- 15344
- ChEMBL
- CHEMBL1230762
- ZINC
- ZINC000000895089
- PDBe Ligand
- AAE
- Wikipedia
- Acetoacetic_acid
- PDB Entries
- 1e3w / 1fcp / 1qco / 1ujw / 1ysl / 2fcp / 2y7g / 3i09 / 3vdr / 6as5 … show 4 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
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) 36.5 °C PhysProp water solubility 1E+006 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) pKa 3.59 (at 0 °C) KORTUM,G ET AL (1961) - Predicted Properties
Property Value Source Water Solubility 240.0 mg/mL ALOGPS logP -0.47 ALOGPS logP -0.0015 Chemaxon logS 0.37 ALOGPS pKa (Strongest Acidic) 4.02 Chemaxon pKa (Strongest Basic) -7.5 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 54.37 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 22.54 m3·mol-1 Chemaxon Polarizability 9.18 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 + 0.9817 Blood Brain Barrier + 0.9678 Caco-2 permeable - 0.5194 P-glycoprotein substrate Non-substrate 0.7736 P-glycoprotein inhibitor I Non-inhibitor 0.9274 P-glycoprotein inhibitor II Non-inhibitor 0.9567 Renal organic cation transporter Non-inhibitor 0.9551 CYP450 2C9 substrate Non-substrate 0.8049 CYP450 2D6 substrate Non-substrate 0.9101 CYP450 3A4 substrate Non-substrate 0.7798 CYP450 1A2 substrate Non-inhibitor 0.9394 CYP450 2C9 inhibitor Non-inhibitor 0.9777 CYP450 2D6 inhibitor Non-inhibitor 0.9614 CYP450 2C19 inhibitor Non-inhibitor 0.9582 CYP450 3A4 inhibitor Non-inhibitor 0.9731 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9924 Ames test Non AMES toxic 0.9424 Carcinogenicity Carcinogens 0.5436 Biodegradation Ready biodegradable 0.9425 Rat acute toxicity 1.8971 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9632 hERG inhibition (predictor II) Non-inhibitor 0.9825
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 114.9697629 predictedDarkChem Lite v0.1.0 [M-H]- 114.8443629 predictedDarkChem Lite v0.1.0 [M-H]- 125.26903 predictedDeepCCS 1.0 (2019) [M+H]+ 115.9002629 predictedDarkChem Lite v0.1.0 [M+H]+ 114.7099629 predictedDarkChem Lite v0.1.0 [M+H]+ 128.03123 predictedDeepCCS 1.0 (2019) [M+Na]+ 114.8130629 predictedDarkChem Lite v0.1.0 [M+Na]+ 115.0199629 predictedDarkChem Lite v0.1.0 [M+Na]+ 136.45262 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsFumarylacetoacetase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- fumarylacetoacetase activity
- Gene Name
- FAH
- Uniprot ID
- P16930
- Uniprot Name
- Fumarylacetoacetase
- Molecular Weight
- 46373.97 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]
Transporters
1. DetailsMonocarboxylate transporter 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Proton-coupled monocarboxylate symporter. Catalyzes the rapid transport across the plasma membrane of monocarboxylates such as L-lactate, pyruvate and ketone bodies, acetoacetate, beta-hydroxybutyrate and acetate (PubMed:32415067, PubMed:9786900). Dimerization is functionally required and both subunits work cooperatively in transporting substrate (PubMed:32415067)
- Specific Function
- identical protein binding
- Gene Name
- SLC16A7
- Uniprot ID
- O60669
- Uniprot Name
- Monocarboxylate transporter 2
- Molecular Weight
- 52199.745 Da
References
- Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [Article]
2. DetailsMonocarboxylate transporter 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Bidirectional proton-coupled monocarboxylate transporter (PubMed:12946269, PubMed:32946811, PubMed:33333023). Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, acetate and the ketone bodies acetoacetate and beta-hydroxybutyrate, and thus contributes to the maintenance of intracellular pH (PubMed:12946269, PubMed:33333023). The transport direction is determined by the proton motive force and the concentration gradient of the substrate monocarboxylate. MCT1 is a major lactate exporter (By similarity). Plays a role in cellular responses to a high-fat diet by modulating the cellular levels of lactate and pyruvate that contribute to the regulation of central metabolic pathways and insulin secretion, with concomitant effects on plasma insulin levels and blood glucose homeostasis (By similarity). Facilitates the protonated monocarboxylate form of succinate export, that its transient protonation upon muscle cell acidification in exercising muscle and ischemic heart (PubMed:32946811). Functions via alternate outward- and inward-open conformation states. Protonation and deprotonation of 309-Asp is essential for the conformational transition (PubMed:33333023)
- Specific Function
- carboxylic acid transmembrane transporter activity
- Gene Name
- SLC16A1
- Uniprot ID
- P53985
- Uniprot Name
- Monocarboxylate transporter 1
- Molecular Weight
- 53943.685 Da
References
- Broer S, Rahman B, Pellegri G, Pellerin L, Martin JL, Verleysdonk S, Hamprecht B, Magistretti PJ: Comparison of lactate transport in astroglial cells and monocarboxylate transporter 1 (MCT 1) expressing Xenopus laevis oocytes. Expression of two different monocarboxylate transporters in astroglial cells and neurons. J Biol Chem. 1997 Nov 28;272(48):30096-102. [Article]
- Broer S, Schneider HP, Broer A, Rahman B, Hamprecht B, Deitmer JW: Characterization of the monocarboxylate transporter 1 expressed in Xenopus laevis oocytes by changes in cytosolic pH. Biochem J. 1998 Jul 1;333 ( Pt 1):167-74. [Article]
3. DetailsMonocarboxylate transporter 4
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Proton-dependent transporter of monocarboxylates such as L-lactate and pyruvate (PubMed:11101640, PubMed:23935841, PubMed:31719150). Plays a predominant role in L-lactate efflux from highly glycolytic cells (By similarity)
- Specific Function
- lactate
- Gene Name
- SLC16A3
- Uniprot ID
- O15427
- Uniprot Name
- Monocarboxylate transporter 4
- Molecular Weight
- 49468.9 Da
References
- Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Acts as an electrogenic sodium (Na(+)) and chloride (Cl-)-dependent sodium-coupled solute transporter, including transport of monocarboxylates (short-chain fatty acids including L-lactate, D-lactate, pyruvate, acetate, propionate, valerate and butyrate), mocarboxylate drugs (nicotinate, benzoate, salicylate and 5-aminosalicylate) and ketone bodies (beta-D-hydroxybutyrate, acetoacetate and alpha-ketoisocaproate), with a Na(+):substrate stoichiometry of between 4:1 and 2:1 (PubMed:14966140, PubMed:15090606, PubMed:16729224, PubMed:16805814, PubMed:17178845, PubMed:17245649, PubMed:17526579, PubMed:20211600, PubMed:30604288). Catalyzes passive carrier mediated diffusion of iodide (PubMed:12107270). Mediates iodide transport from the thyrocyte into the colloid lumen through the apical membrane (PubMed:12107270). May be responsible for the absorption of D-lactate and monocarboxylate drugs from the intestinal tract (PubMed:17245649). Acts as a tumor suppressor, suppressing colony formation in colon cancer, prostate cancer and glioma cell lines (PubMed:12829793, PubMed:15867356, PubMed:18037591). May play a critical role in the entry of L-lactate and ketone bodies into neurons by a process driven by an electrochemical Na(+) gradient and hence contribute to the maintenance of the energy status and function of neurons (PubMed:16805814). Mediates sodium-coupled electrogenic transport of pyroglutamate (5-oxo-L-proline) (PubMed:20211600). Can mediate the transport of chloride, bromide, iodide and nitrate ions when the external concentration of sodium ions is reduced (PubMed:19864324)
- Specific Function
- lactate transmembrane transporter activity
- Gene Name
- SLC5A8
- Uniprot ID
- Q8N695
- Uniprot Name
- Sodium-coupled monocarboxylate transporter 1
- Molecular Weight
- 66577.005 Da
References
- Martin PM, Gopal E, Ananth S, Zhuang L, Itagaki S, Prasad BM, Smith SB, Prasad PD, Ganapathy V: Identity of SMCT1 (SLC5A8) as a neuron-specific Na+-coupled transporter for active uptake of L-lactate and ketone bodies in the brain. J Neurochem. 2006 Jul;98(1):279-88. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52