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Record Information
Version2.0
Creation Date2014-09-11 05:15:59 UTC
Update Date2014-12-24 20:26:57 UTC
Accession NumberT3D4773
Identification
Common NameCapric acid
ClassSmall Molecule
DescriptionCapric acid is a member of the series of fatty acids found in oils and animal fats. The names of Caproic, Caprylic, and Capric acids are all derived from the word caper (Latin: 'goat'). These are colorless light yellowish transparent oily liquids with unconfortable smells. These are used in organic synthesis, manufacture of perfume, medicine, lubricating grease, rubber and dye.
Compound Type
  • Animal Toxin
  • Antifungal Agent
  • Dye
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1-Nonanecarboxylate
1-Nonanecarboxylic acid
Caprate
Caprinate
Caprinic acid
Caprynate
Caprynic acid
Decoate
Decoic acid
Decylate
Decylic acid
Emery 659
Lunac 10-95
Lunac 10-98
N-Caprate
N-Capric acid
N-Decanoate
N-Decanoic acid
N-Decoate
N-Decoic acid
N-Decylate
N-Decylic acid
Prifac 2906
Prifac 296
Chemical FormulaC10H20O2
Average Molecular Mass172.265 g/mol
Monoisotopic Mass172.146 g/mol
CAS Registry Number334-48-5
IUPAC Namedecanoic acid
Traditional Namecapric acid
SMILESCCCCCCCCCC(O)=O
InChI IdentifierInChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)
InChI KeyInChIKey=GHVNFZFCNZKVNT-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Beta Oxidation of Very Long Chain Fatty AcidsSMP00052 map01040
Fatty Acid BiosynthesisSMP00456 map00061
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point31.9°C
Boiling Point268.7°C
Solubility61.8 mg/L (at 25°C)
LogP4.09
Predicted Properties
PropertyValueSource
Water Solubility0.095 g/LALOGPS
logP3.93ALOGPS
logP3.59ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.48 m³·mol⁻¹ChemAxon
Polarizability21.61 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017i-2920000000-7f6721f01b80a790d5442014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-076u-9000000000-96a2e9e00e464db3c0862017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-017i-2920000000-7f6721f01b80a790d5442017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-016r-1910000000-1cc1026f6f325d994ab42017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052g-9200000000-71a57b0e200e46fb66ed2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9300000000-c615f39c0b907a00f67c2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-0a7f944302bce161f7e52012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00b9-1900000000-b68efbceecf3433a99952012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-005a-9600000000-f2a54ed1a56ee9b7af772012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-076u-9000000000-96a2e9e00e464db3c0862012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-771e7907916bf05e6b102012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-f1e000384728ee06f8022012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-1900000000-42a901bb54546da030da2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-83e77de04461ded1c4bc2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-f3190b828218d04d3cc72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0000000910-e82208ed71b4a37352582017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a92017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a92017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-00di-0900000000-8c6cdf0491f51ba6ef262017-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-856f34ef153b15cb3d1d2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-4900000000-efb0bd73973bf0c317fd2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-d81148541fa575d325522015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-99cd0519b210c46b4a4c2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fmi-1900000000-209285ec682ca47e1e5d2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-fb697080d761d0f48fe22015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-856f34ef153b15cb3d1d2015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-4900000000-efb0bd73973bf0c317fd2015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-d81148541fa575d325522015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-99cd0519b210c46b4a4c2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fmi-1900000000-209285ec682ca47e1e5d2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-fb697080d761d0f48fe22015-05-27View Spectrum
MSMass Spectrum (Electron Ionization)splash10-074l-9100000000-bf788cb34c09c6af56bf2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not Available2012-12-05View Spectrum
Toxicity Profile
Route of ExposureDermal (MSDS) ; eye contact (MSDS) ; inhalation (MSDS); oral (MSDS)
Mechanism of ToxicityIt 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 (19, 20). These fatty acids were also shown to induce oxidative stress in the brain (21). Experiments suggest that OA and DA impair brain mitochondrial energy homeostasis that could underlie at least in part the neuropathology of MCADD. (22)
MetabolismCapric acid (decanoic acid) is rapidly metabolized by the β-oxidative pathway, giving rise to C8- and C6-dicarboxylic acids (23). 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 ValuesLD50: 3730 mg/kg (Oral, Rat) (MSDS) LD50: 1770 mg/kg (Dermal, Rabbit) (MSDS)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (25)
Uses/SourcesCapric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils. It is found in the milk of various mammals and to a lesser extent in other animal fats. Capric acid is used in the manufacturing of esters for artificial fruit flavors and perfumes. It is also use as an intermediate in chemical syntheses. It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals. (Wikipedia)
Minimum Risk LevelNot Available
Health EffectsOctanoic (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. (22)
SymptomsMCADD presents in early childhood with hypoketotic hypoglycemia and liver dysfunction, often preceded by extended periods of fasting or an infection with vomiting. Infants who are exclusively breast-fed may present in this manner shortly after birth, due to poor feeding. In some individuals the first manifestation of MCADD may be sudden death following a minor illness. A number of individuals with MCADD may remain completely asymptomatic, provided they never encounter a situation that sufficiently stresses their metabolism. (Wikipedia) Irritating to the skin, lung, or gastrointestinal tract, depending on the route of exposure (MSDS).
TreatmentManagement 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. (22)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB03600
HMDB IDHMDB00511
PubChem Compound ID2969
ChEMBL IDCHEMBL107498
ChemSpider ID2863
KEGG IDC01571
UniProt IDNot Available
OMIM ID
ChEBI ID30813
BioCyc ID3-OXODODECANOATE
CTD IDNot Available
Stitch IDDecanoic acid
PDB IDDKA
ACToR ID1566
Wikipedia LinkCapric acid
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Farrington CJ, Chalmers AH: Gas-chromatographic estimation of urinary oxalate and its comparison with a colorimetric method. Clin Chem. 1979 Dec;25(12):1993-6. [509698 ]
  2. Lima TM, Kanunfre CC, Pompeia C, Verlengia R, Curi R: Ranking the toxicity of fatty acids on Jurkat and Raji cells by flow cytometric analysis. Toxicol In Vitro. 2002 Dec;16(6):741-7. [12423658 ]
  3. Wanten GJ, Janssen FP, Naber AH: Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length. Eur J Clin Invest. 2002 Apr;32(4):285-9. [11952815 ]
  4. Lindmark T, Kimura Y, Artursson P: Absorption enhancement through intracellular regulation of tight junction permeability by medium chain fatty acids in Caco-2 cells. J Pharmacol Exp Ther. 1998 Jan;284(1):362-9. [9435199 ]
  5. Kaiya H, Van Der Geyten S, Kojima M, Hosoda H, Kitajima Y, Matsumoto M, Geelissen S, Darras VM, Kangawa K: Chicken ghrelin: purification, cDNA cloning, and biological activity. Endocrinology. 2002 Sep;143(9):3454-63. [12193558 ]
  6. Eriksson T, Bjorkman S, Roth B, Fyge A, Hoglund P: Enantiomers of thalidomide: blood distribution and the influence of serum albumin on chiral inversion and hydrolysis. Chirality. 1998;10(3):223-8. [9499573 ]
  7. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [12829005 ]
  8. Da Silva MA, Medeiros VC, Langone MA, Freire DM: Synthesis of monocaprin catalyzed by lipase. Appl Biochem Biotechnol. 2003 Spring;105 -108:757-67. [12721413 ]
  9. Imai T, Sakai M, Ohtake H, Azuma H, Otagiri M: Absorption-enhancing effect of glycyrrhizin induced in the presence of capric acid. Int J Pharm. 2005 Apr 27;294(1-2):11-21. [15814227 ]
  10. Leopold CS, Lippold BC: An attempt to clarify the mechanism of the penetration enhancing effects of lipophilic vehicles with differential scanning calorimetry (DSC). J Pharm Pharmacol. 1995 Apr;47(4):276-81. [7791023 ]
  11. Saso L, Valentini G, Grippa E, Leone MG, Silvestrini B: Effect of selected substances on heat-induced aggregation of albumin, IgG and lysozyme. Res Commun Mol Pathol Pharmacol. 1998 Oct;102(1):15-28. [9920343 ]
  12. Kaiya H, Kojima M, Hosoda H, Riley LG, Hirano T, Grau EG, Kangawa K: Identification of tilapia ghrelin and its effects on growth hormone and prolactin release in the tilapia, Oreochromis mossambicus. Comp Biochem Physiol B Biochem Mol Biol. 2003 Jul;135(3):421-9. [12831762 ]
  13. Coyne CB, Ribeiro CM, Boucher RC, Johnson LG: Acute mechanism of medium chain fatty acid-induced enhancement of airway epithelial permeability. J Pharmacol Exp Ther. 2003 May;305(2):440-50. Epub 2003 Feb 11. [12606647 ]
  14. Tanaka S, Saitoh O, Tabata K, Matsuse R, Kojima K, Sugi K, Nakagawa K, Kayazawa M, Teranishi T, Uchida K, Hirata I, Katsu K: Medium-chain fatty acids stimulate interleukin-8 production in Caco-2 cells with different mechanisms from long-chain fatty acids. J Gastroenterol Hepatol. 2001 Jul;16(7):748-54. [11446882 ]
  15. Duran M, Mitchell G, de Klerk JB, de Jager JP, Hofkamp M, Bruinvis L, Ketting D, Saudubray JM, Wadman SK: Octanoic acidemia and octanoylcarnitine excretion with dicarboxylic aciduria due to defective oxidation of medium-chain fatty acids. J Pediatr. 1985 Sep;107(3):397-404. [4032135 ]
  16. Wallon C, Braaf Y, Wolving M, Olaison G, Soderholm JD: Endoscopic biopsies in Ussing chambers evaluated for studies of macromolecular permeability in the human colon. Scand J Gastroenterol. 2005 May;40(5):586-95. [16036512 ]
  17. Van Immerseel F, De Buck J, Boyen F, Bohez L, Pasmans F, Volf J, Sevcik M, Rychlik I, Haesebrouck F, Ducatelle R: Medium-chain fatty acids decrease colonization and invasion through hilA suppression shortly after infection of chickens with Salmonella enterica serovar Enteritidis. Appl Environ Microbiol. 2004 Jun;70(6):3582-7. [15184160 ]
  18. Kamata Y, Shiraga H, Tai A, Kawamoto Y, Gohda E: Induction of neurite outgrowth in PC12 cells by the medium-chain fatty acid octanoic acid. Neuroscience. 2007 May 25;146(3):1073-81. Epub 2007 Apr 16. [17434686 ]
  19. Scholz R, Schwabe U, Soboll S: Influence of fatty acids on energy metabolism. 1. Stimulation of oxygen consumption, ketogenesis and CO2 production following addition of octanoate and oleate in perfused rat liver. Eur J Biochem. 1984 May 15;141(1):223-30. [6426957 ]
  20. Reis de Assis D, Maria Rde C, Borba Rosa R, Schuck PF, Ribeiro CA, da Costa Ferreira G, Dutra-Filho CS, Terezinha de Souza Wyse A, Duval Wannmacher CM, Santos Perry ML, Wajner M: Inhibition of energy metabolism in cerebral cortex of young rats by the medium-chain fatty acids accumulating in MCAD deficiency. Brain Res. 2004 Dec 24;1030(1):141-51. [15567346 ]
  21. Schuck PF, Ferreira GC, Moura AP, Busanello EN, Tonin AM, Dutra-Filho CS, Wajner M: Medium-chain fatty acids accumulating in MCAD deficiency elicit lipid and protein oxidative damage and decrease non-enzymatic antioxidant defenses in rat brain. Neurochem Int. 2009 Jul;54(8):519-25. doi: 10.1016/j.neuint.2009.02.009. Epub 2009 Feb 24. [19428797 ]
  22. Schuck PF, Ferreira Gda C, Tonin AM, Viegas CM, Busanello EN, Moura AP, Zanatta A, Klamt F, Wajner M: Evidence that the major metabolites accumulating in medium-chain acyl-CoA dehydrogenase deficiency disturb mitochondrial energy homeostasis in rat brain. Brain Res. 2009 Nov 3;1296:117-26. doi: 10.1016/j.brainres.2009.08.053. Epub 2009 Aug 21. [19703432 ]
  23. Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
  24. Currance PL, Clements B, Bronstein AC (eds) (2005). Emergency Care For Hazardous Materials Exposure. 3rd ed. St. Louis, MO: Elsevier Mosby.
  25. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

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
  1. 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:
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
  1. 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:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. Required for limb bud development. In concert with RARA or RARB, required for skeletal growth, matrix homeostasis and growth plate function (By similarity).
Gene Name:
RARG
Uniprot ID:
P13631
Molecular Weight:
50341.405 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC502.67 uMATG_RARg_TRANSAttagene
References
  1. 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:
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC503.49 uMNVS_GPCR_hAdoRA1Novascreen
References
  1. 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 ]