Identification
- Generic Name
- Acetoacetic acid
- DrugBank Accession Number
- DB01762
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Acetoacetic acid (DB01762)
- 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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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
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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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Metal ion binding
- Specific Function
- Not Available
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Symporter activity
- Specific Function
- Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Symporter activity
- Specific Function
- Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine...
- 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
- Symporter activity
- Specific 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-lactat...
- 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