3-Methyl-2-oxobutyric acid
Relevant Data
Food Additives Approved in the United States:
Food Additives Approved by WHO:
General Information
| Chemical name | 3-Methyl-2-oxobutyric acid |
| CAS number | 759-05-7 |
| COE number | 2262 |
| JECFA number | 631 |
| Flavouring type | substances |
| FL No. | 08.051 |
| Mixture | No |
| Purity of the named substance at least 95% unless otherwise specified | |
| Reference body | JECFA |
From webgate.ec.europa.eu
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 49 |
| IUPAC Name | 3-methyl-2-oxobutanoic acid |
| InChI | InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8) |
| InChI Key | QHKABHOOEWYVLI-UHFFFAOYSA-N |
| Canonical SMILES | CC(C)C(=O)C(=O)O |
| Molecular Formula | C5H8O3 |
| Wikipedia | 3-methyl-2-oxobutanoate |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 116.116 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 115.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B g M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A D Q S A g A A C C A A A A g A I A I C Q C A I A A A A A A A A A A A F A A A A A A B A A A A A A Q A A E A A A A A A A A A A A I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 54.4 |
| Monoisotopic Mass | 116.047 |
| Exact Mass | 116.047 |
| XLogP3 | None |
| XLogP3-AA | 0.7 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 8 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9371 |
| Human Intestinal Absorption | HIA+ | 0.9764 |
| Caco-2 Permeability | Caco2- | 0.6143 |
| P-glycoprotein Substrate | Non-substrate | 0.7906 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9239 |
| Non-inhibitor | 0.9466 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9548 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8824 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8246 |
| CYP450 2D6 Substrate | Non-substrate | 0.9285 |
| CYP450 3A4 Substrate | Non-substrate | 0.7040 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9811 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9109 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9584 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9804 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9813 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9905 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9939 |
| Non-inhibitor | 0.9736 | |
| AMES Toxicity | Non AMES toxic | 0.9163 |
| Carcinogens | Carcinogens | 0.5840 |
| Fish Toxicity | High FHMT | 0.5152 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9597 |
| Honey Bee Toxicity | High HBT | 0.7319 |
| Biodegradation | Ready biodegradable | 0.8850 |
| Acute Oral Toxicity | III | 0.6948 |
| Carcinogenicity (Three-class) | Non-required | 0.8040 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.0172 | LogS |
| Caco-2 Permeability | 0.6555 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.5628 | LD50, mol/kg |
| Fish Toxicity | 3.2248 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.8584 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | None |
|---|---|
| Mechanism of Toxicity | None |
| Metabolism | None |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | Chronically high levels of alpha-ketoisovaleric acid are associated with Maple Syrup Urine Disease. |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Keto acids and derivatives |
| Subclass | Short-chain keto acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Short-chain keto acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Branched fatty acid - Methyl-branched fatty acid - Short-chain keto acid - Alpha-keto acid - Fatty acyl - Alpha-hydroxy ketone - Ketone - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Carbonyl group - Hydrocarbon derivative - Organic oxygen compound - Organooxygen compound - Organic oxide - Aliphatic acyclic compound |
| 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. |
From ClassyFire
Targets
- General Function:
- L-valine transaminase activity
- Specific Function:
- Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids.
- Gene Name:
- BCAT2
- Uniprot ID:
- O15382
- Molecular Weight:
- 44287.445 Da
References
- 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. [17016423 ]
- General Function:
- Metal ion binding
- Specific Function:
- Catalyzes the reversible reaction in which hydroxymethyl group from 5,10-methylenetetrahydrofolate is tranferred onto alpha-ketoisovalerate to form ketopantoate.
- Gene Name:
- panB
- Uniprot ID:
- Q9JZW6
- Molecular Weight:
- 27739.07 Da
- General Function:
- L-ascorbic acid binding
- Specific Function:
- Catalyzes the step from penicillin N to deacetoxy-cephalosporin C.
- Gene Name:
- cefE
- Uniprot ID:
- P18548
- Molecular Weight:
- 34555.38 Da
- General Function:
- Catalyzes the condensation of the acetyl group of acetyl-CoA with 3-methyl-2-oxobutanoate (2-oxoisovalerate) to form 3-carboxy-3-hydroxy-4-methylpentanoate (2-isopropylmalate).
- Specific Function:
- 2-isopropylmalate synthase activity
- Gene Name:
- leuA
- Uniprot ID:
- P9WQB3
- Molecular Weight:
- 70112.945 Da
From T3DB