Decanoic acid
Relevant Data
Food Additives Approved in the United States:
Food Additives Approved by WHO:
General Information
| Chemical name | Decanoic acid |
| CAS number | 334-48-5 |
| COE number | 11 |
| JECFA number | 105 |
| Flavouring type | substances |
| FL No. | 08.011 |
| 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 | 2969 |
| IUPAC Name | decanoic acid |
| InChI | InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) |
| InChI Key | GHVNFZFCNZKVNT-UHFFFAOYSA-N |
| Canonical SMILES | CCCCCCCCCC(=O)O |
| Molecular Formula | C10H20O2 |
| Wikipedia | capric acid |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 172.268 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 8 |
| Complexity | 110.0 |
| CACTVS Substructure Key Fingerprint | A A A D c e B w 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 C A C A g A A C C A A A A g A I A A C Q C A A A A A A A A A A A A A E A A A A A A B I A A A A A Q A A E A A A A A A G I y K C 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 = = |
| Topological Polar Surface Area | 37.3 |
| Monoisotopic Mass | 172.146 |
| Exact Mass | 172.146 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| 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+ | 0.9488 |
| Human Intestinal Absorption | HIA+ | 0.9888 |
| Caco-2 Permeability | Caco2+ | 0.8326 |
| P-glycoprotein Substrate | Non-substrate | 0.6321 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9598 |
| Non-inhibitor | 0.9277 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9266 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5152 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7886 |
| CYP450 2D6 Substrate | Non-substrate | 0.8956 |
| CYP450 3A4 Substrate | Non-substrate | 0.6982 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8326 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8808 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9554 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9578 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9484 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9647 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9322 |
| Non-inhibitor | 0.8868 | |
| AMES Toxicity | Non AMES toxic | 0.9865 |
| Carcinogens | Non-carcinogens | 0.6452 |
| Fish Toxicity | High FHMT | 0.9144 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9990 |
| Honey Bee Toxicity | High HBT | 0.6691 |
| Biodegradation | Ready biodegradable | 0.8795 |
| Acute Oral Toxicity | IV | 0.6378 |
| Carcinogenicity (Three-class) | Non-required | 0.7057 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.5022 | LogS |
| Caco-2 Permeability | 1.3950 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.3275 | LD50, mol/kg |
| Fish Toxicity | 1.8920 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3852 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Dermal (MSDS) ; eye contact (MSDS) ; inhalation (MSDS); oral (MSDS) |
|---|---|
| Mechanism of Toxicity | It has been demonstrated that octanoic (OA) and decanoic (DA) acids compromise the glycolytic pathway and citric acid cycle functioning, increase oxygen consumption in the liver and inhibit some activities of the respiratory chain complexes and creatine kinase in rat brain . These fatty acids were also shown to induce oxidative stress in the brain . Experiments suggest that OA and DA impair brain mitochondrial energy homeostasis that could underlie at least in part the neuropathology of MCADD. |
| Metabolism | Capric acid (decanoic acid) is rapidly metabolized by the β-oxidative pathway, giving rise to C8- and C6-dicarboxylic acids . The enzyme MCAD (medium-chain acyl-CoA dehydrogenase) is responsible for the dehydrogenation step of fatty acids with chain lengths between 6 and 12 carbons as they undergo beta-oxidation in the mitochondria. Fatty acid beta-oxidation provides energy after the body has used up its stores of glucose and glycogen. This typically occurs during periods of extended fasting or illness when caloric intake is reduced, and energy needs are increased. Beta-oxidation of long chain fatty acids produces two carbon units, acetyl-CoA and the reducing equivalents NADH and FADH2. NADH and FADH2 enter the electron transport chain and are used to make ATP. Acetyl-CoA enters the Krebs Cycle and is also used to make ATP via the electron transport chain and substrate level phosphorylation. When the supply of acetyl-CoA (coming from the beta-oxidation of fatty acids) exceeds the capacity of the Krebs Cycle to metabolize acetyl-CoA, the excess acetyl-CoA molecules are converted to ketone bodies (acetoacetate and beta-hydroxybutyrate) by HMG-CoA synthase in the liver. Ketone bodies can also be used for energy especially by the brain and heart; in fact they become the main sources of energy for those two organs after day three of starvation. (Wikipedia) |
| Toxicity Values | LD50: 3730 mg/kg (Oral, Rat) (MSDS) LD50: 1770 mg/kg (Dermal, Rabbit) (MSDS) |
| Lethal Dose | |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity (not listed by IARC). |
| Minimum Risk Level | |
| Health Effects | Octanoic (OA) and decanoic (DA) acids are the predominant metabolites accumulating in medium-chain acyl-CoA dehydrogenase (MCAD; E.C. 1.3.99.3) deficiency (MCADD), the most common inherited defect of fatty acid oxidation. Glycine and l-carnitine bind to these fatty acids giving rise to derivatives that also accumulate in this disorder. The clinical presentation typically occurs in early childhood but can occasionally be delayed until adulthood. The major features of the disease include hypoglycemia, vomiting, lethargy and encephalopathy after fasting, infection or other metabolic stressors. (A15457) |
| Treatment | Management of acute MCADD includes rapid correction of hypoglycemia, rehydration and treatment of the underlying infection or other stress factor. Current long-term therapy includes avoidance of fasting and a high carbohydrate low-fat diet, but it does not fully prevent the crises and the neurological alterations. |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty acids and conjugates |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Medium-chain fatty acids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Medium-chain fatty acid - Straight chain fatty acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
From ClassyFire
Targets
- General Function:
- Serine-type endopeptidase inhibitor activity
- Specific Function:
- Furin is likely to represent the ubiquitous endoprotease activity within constitutive secretory pathways and capable of cleavage at the RX(K/R)R consensus motif.
- Gene Name:
- FURIN
- Uniprot ID:
- P09958
- Molecular Weight:
- 86677.375 Da
References
- 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. [10592235 ]
- General Function:
- Purine nucleoside binding
- Specific Function:
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name:
- ADORA1
- Uniprot ID:
- P30542
- Molecular Weight:
- 36511.325 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Lipid binding
- Specific Function:
- Accelerates the intermembrane transfer of various glycolipids. Catalyzes the transfer of various glycosphingolipids between membranes but does not catalyze the transfer of phospholipids. May be involved in the intracellular translocation of glucosylceramides.
- Gene Name:
- GLTP
- Uniprot ID:
- Q9NZD2
- Molecular Weight:
- 23849.6 Da
References
- 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. [10592235 ]
- General Function:
- 3-oxoacyl-[acyl-carrier-protein] synthase activity
- Specific Function:
- Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Specific for elongation from C-10 to unsaturated C-16 and C-18 fatty acids.
- Gene Name:
- fabB
- Uniprot ID:
- P0A953
- Molecular Weight:
- 42612.995 Da
- Specific Function:
- Binds serum albumin.
- Gene Name:
- pab
- Uniprot ID:
- Q51911
- Molecular Weight:
- 43057.45 Da
- General Function:
- Catalyzes the transfer of endogenously produced octanoic acid from octanoyl-acyl-carrier-protein onto the lipoyl domains of lipoate-dependent enzymes. Lipoyl-ACP can also act as a substrate although octanoyl-ACP is likely to be the physiological substrate.
- Specific Function:
- Lipoyl(octanoyl) transferase activity
- Gene Name:
- lipB
- Uniprot ID:
- P9WK83
- Molecular Weight:
- 24210.415 Da
- General Function:
- Metal ion binding
- Gene Name:
- tcp14
- Uniprot ID:
- Q6ZZJ1
- Molecular Weight:
- 30067.18 Da
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 Da
From T3DB