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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-08-17 21:43:48 UTC
HMDB IDHMDB00511
Secondary Accession NumbersNone
Metabolite Identification
Common NameCapric acid
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.(ChemicalLAND21).
Structure
Thumb
Synonyms
ValueSource
1-Nonanecarboxylic acidChEBI
10:0ChEBI
C10:0ChEBI
Caprinic acidChEBI
CH3-[CH2]8-COOHChEBI
DecanoateChEBI
Decoic acidChEBI
Decylic acidChEBI
DekansaeureChEBI
KaprinsaeureChEBI
N-Capric acidChEBI
N-Decanoic acidChEBI
N-Decoic acidChEBI
N-Decylic acidChEBI
1-NonanecarboxylateGenerator
CaprinateGenerator
DecoateGenerator
DecylateGenerator
N-CaprateGenerator
N-DecanoateGenerator
N-DecoateGenerator
N-DecylateGenerator
CaprateHMDB
CaprynateHMDB
Caprynic acidHMDB
Emery 659HMDB
Lunac 10-95HMDB
Lunac 10-98HMDB
Prifac 2906HMDB
Prifac 296HMDB
Chemical FormulaC10H20O2
Average Molecular Weight172.2646
Monoisotopic Molecular Weight172.146329884
IUPAC Namedecanoic acid
Traditional Namecapric acid
CAS Registry Number334-48-5
SMILES
CCCCCCCCCC(O)=O
InChI Identifier
InChI=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
DescriptionThis 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.
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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point31.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0618 mg/mLNot Available
LogP4.09HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.095 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.48 m3·mol-1ChemAxon
Polarizability21.61 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017i-2920000000-7f6721f01b80a790d544View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-0a7f944302bce161f7e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00b9-1900000000-b68efbceecf3433a9995View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-005a-9600000000-f2a54ed1a56ee9b7af77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-076u-9000000000-96a2e9e00e464db3c086View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-771e7907916bf05e6b10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-f1e000384728ee06f802View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-1900000000-42a901bb54546da030daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-83e77de04461ded1c4bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-f3190b828218d04d3cc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-856f34ef153b15cb3d1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-4900000000-efb0bd73973bf0c317fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-d81148541fa575d32552View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-99cd0519b210c46b4a4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fmi-1900000000-209285ec682ca47e1e5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-fb697080d761d0f48fe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-856f34ef153b15cb3d1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-4900000000-efb0bd73973bf0c317fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-d81148541fa575d32552View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-99cd0519b210c46b4a4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fmi-1900000000-209285ec682ca47e1e5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-fb697080d761d0f48fe2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-074l-9100000000-bf788cb34c09c6af56bfView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Breast Milk
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Beta Oxidation of Very Long Chain Fatty AcidsSMP00052map01040
Fatty Acid BiosynthesisSMP00456Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.0 (5.0-17.0) uMAdult (>18 years old)BothNormal details
Breast MilkDetected and Quantified53.7 +/- 19.3 uMAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Not AvailableNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
UrineDetected and Quantified10.607 +/- 3.815 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
UrineDetected and Quantified9.517 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03600
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012027
KNApSAcK IDC00001213
Chemspider ID2863
KEGG Compound IDC01571
BioCyc ID3-OXODODECANOATE
BiGG IDNot Available
Wikipedia LinkCapric acid
NuGOwiki LinkHMDB00511
Metagene LinkHMDB00511
METLIN ID336
PubChem Compound2969
PDB IDDKA
ChEBI ID30813
References
Synthesis ReferenceWang, Qin; Ni, Xindi; Shi, Jianying. Manufacturing technology of capric acid and hydroxyalkyl amide from Litsea cubeba nucleolus oil. Huaxue Shijie (1993), 34(2), 84-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  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 ]

Enzymes

General function:
Involved in acyltransferase activity
Specific function:
Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate. Converts the end product of pristanic acid beta oxidation, 4,8-dimethylnonanoyl-CoA, to its corresponding carnitine ester.
Gene Name:
CROT
Uniprot ID:
Q9UKG9
Molecular weight:
10213.63
General function:
Involved in acyltransferase activity
Specific function:
Not Available
Gene Name:
CPT2
Uniprot ID:
P23786
Molecular weight:
73776.335
General function:
Involved in transporter activity
Specific function:
Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:
SLC25A20
Uniprot ID:
O43772
Molecular weight:
32943.46
General function:
Involved in serine-type endopeptidase 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:
86677.4
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:
Involved in glycolipid transporter activity
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
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 ]