Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Isobutyric acid
- DrugBank Accession Number
- DB02531
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Isobutyric acid (DB02531)
- Weight
- Average: 88.1051
Monoisotopic: 88.0524295 - Chemical Formula
- C4H8O2
- Synonyms
- 2-methyl-propionic acid
- 2-Methylpropanoate
- 2-Methylpropanoic acid
- 2-Methylpropionsäure
- 2,2-dimethylacetic acid
- Dimethylacetic acid
- iso-butyric acid
- Isobutanoate
- Isobuttersäure
- Isobutyrate
- Isopropylformic acid
- α-isobutyric acid
- α-methylpropanoic acid
- α-methylpropionic acid
- External IDs
- FEMA NO. 2222
- NSC-62780
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism AFree fatty acid receptor 2 agonistHumans U2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase Not Available Pseudomonas fluorescens - 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Carboxylic acids
- Direct Parent
- Carboxylic acids
- Alternative Parents
- Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- branched-chain saturated fatty acid, methyl-branched fatty acid, short-chain fatty acid (CHEBI:16135) / Branched fatty acids (LMFA01020071)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 8LL210O1U0
- CAS number
- 79-31-2
- InChI Key
- KQNPFQTWMSNSAP-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
- IUPAC Name
- 2-methylpropanoic acid
- SMILES
- CC(C)C(O)=O
References
- Synthesis Reference
Richard V. Norton, Lee R. Zehner, Ralph F. Pascoe, John E. Corn, Jr., Dace Grote, "Process for the production of isobutyric acid anhydride." U.S. Patent US4303594, issued September, 1936.
US4303594- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001873
- KEGG Compound
- C02632
- PubChem Compound
- 6590
- PubChem Substance
- 46506341
- ChemSpider
- 6341
- ChEBI
- 16135
- ChEMBL
- CHEMBL108778
- ZINC
- ZINC000000901420
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- ALQ
- Wikipedia
- Isobutyric_acid
- PDB Entries
- 1iup / 1qr3 / 1r6n / 4gm3 / 4gm8 / 4gm9 / 4gmb / 7axp / 7axq / 7axs … show 2 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) -46 °C PhysProp boiling point (°C) 154.4 °C PhysProp water solubility 1.67E+005 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.94 SANGSTER (1993) logS 0.28 ADME Research, USCD pKa 4.84 (at 20 °C) KORTUM,G ET AL (1961) - Predicted Properties
Property Value Source Water Solubility 197.0 mg/mL ALOGPS logP 0.78 ALOGPS logP 1.02 Chemaxon logS 0.35 ALOGPS pKa (Strongest Acidic) 4.87 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 21.85 m3·mol-1 Chemaxon Polarizability 9.12 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9848 Blood Brain Barrier + 0.9624 Caco-2 permeable + 0.598 P-glycoprotein substrate Non-substrate 0.8363 P-glycoprotein inhibitor I Non-inhibitor 0.9839 P-glycoprotein inhibitor II Non-inhibitor 0.9897 Renal organic cation transporter Non-inhibitor 0.953 CYP450 2C9 substrate Non-substrate 0.7927 CYP450 2D6 substrate Non-substrate 0.9404 CYP450 3A4 substrate Non-substrate 0.7385 CYP450 1A2 substrate Non-inhibitor 0.95 CYP450 2C9 inhibitor Non-inhibitor 0.9496 CYP450 2D6 inhibitor Non-inhibitor 0.9649 CYP450 2C19 inhibitor Non-inhibitor 0.9886 CYP450 3A4 inhibitor Non-inhibitor 0.9818 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9908 Ames test Non AMES toxic 0.9873 Carcinogenicity Carcinogens 0.6966 Biodegradation Ready biodegradable 0.8574 Rat acute toxicity 1.6341 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9881 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]- 109.9793425 predictedDarkChem Lite v0.1.0 [M-H]- 110.0891425 predictedDarkChem Lite v0.1.0 [M-H]- 126.67056 predictedDeepCCS 1.0 (2019) [M+H]+ 129.46803 predictedDeepCCS 1.0 (2019) [M+Na]+ 137.6445 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- G protein-coupled receptor that is activated by a major product of dietary fiber digestion, the short chain fatty acids (SCFAs), and that plays a role in the regulation of whole-body energy homeostasis and in intestinal immunity. In omnivorous mammals, the short chain fatty acids acetate, propionate and butyrate are produced primarily by the gut microbiome that metabolizes dietary fibers. SCFAs serve as a source of energy but also act as signaling molecules. That G protein-coupled receptor is probably coupled to the pertussis toxin-sensitive, G(i/o)-alpha family of G proteins but also to the Gq family (PubMed:12496283, PubMed:12711604, PubMed:23589301). Its activation results in the formation of inositol 1,4,5-trisphosphate, the mobilization of intracellular calcium, the phosphorylation of the MAPK3/ERK1 and MAPK1/ERK2 kinases and the inhibition of intracellular cAMP accumulation. May play a role in glucose homeostasis by regulating the secretion of GLP-1, in response to short-chain fatty acids accumulating in the intestine. May also regulate the production of LEP/Leptin, a hormone acting on the central nervous system to inhibit food intake. Finally, may also regulate whole-body energy homeostasis through adipogenesis regulating both differentiation and lipid storage of adipocytes. In parallel to its role in energy homeostasis, may also mediate the activation of the inflammatory and immune responses by SCFA in the intestine, regulating the rapid production of chemokines and cytokines. May also play a role in the resolution of the inflammatory response and control chemotaxis in neutrophils. In addition to SCFAs, may also be activated by the extracellular lectin FCN1 in a process leading to activation of monocytes and inducing the secretion of interleukin-8/IL-8 in response to the presence of microbes (PubMed:21037097). Among SCFAs, the fatty acids containing less than 6 carbons, the most potent activators are probably acetate, propionate and butyrate (PubMed:12496283, PubMed:12711604). Exhibits a SCFA-independent constitutive G protein-coupled receptor activity (PubMed:23066016)
- Specific Function
- G protein-coupled receptor activity
- Gene Name
- FFAR2
- Uniprot ID
- O15552
- Uniprot Name
- Free fatty acid receptor 2
- Molecular Weight
- 37143.375 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Pseudomonas fluorescens
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- hydrolase activity
- Gene Name
- cumD
- Uniprot ID
- P96965
- Uniprot Name
- 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase
- Molecular Weight
- 31489.385 Da
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:21