Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-08-17 00:40:15 UTC
HMDB IDHMDB0000791
Secondary Accession Numbers
  • HMDB0000834
  • HMDB00791
  • HMDB00834
Metabolite Identification
Common NameOctanoylcarnitine
DescriptionL-Octanoylcarnitine is the physiologically active form of octanoylcarnitine (PMID: 11274033 ). Octanoylcarnitine is detected in medium-chain acyl-CoA dehydrogenase (MCAD) deficiency. MCAD is characterized by an intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels (OMIM: 201450 ). L-Octanoylcarnitine is also found to be associated with celiac disease and glutaric aciduria II, which are inborn errors of metabolism.
Structure
Data?1660696815
Synonyms
ValueSource
L-Octanoyl-L-carnitineChEBI
O-Octanoyl-(R)-carnitineChEBI
O-Octanoyl-R-carnitineChEBI
(-)-OctanoylcarnitineHMDB
L-Carnitine octanoyl esterHMDB
L-O-OctanoylcarnitineHMDB
Octanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner saltHMDB
Octanoyl-L-carnitineHMDB
OctanoylcarnitineHMDB
Octanoylcarnitine chloride, (R)-isomerHMDB
Octanoylcarnitine, (R)-isomerHMDB
Octanoylcarnitine chlorideHMDB
Octanoylcarnitine chloride, (+-)-isomerHMDB
Octanoylcarnitine, (+-)-isomerHMDB
C8-CarnitineHMDB
L-OctanoylcarnitineChEBI
Chemical FormulaC15H29NO4
Average Molecular Weight287.3951
Monoisotopic Molecular Weight287.209658421
IUPAC Name(3R)-3-(octanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional NameL-octanoylcarnitine
CAS Registry Number25243-95-2
SMILES
CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C15H29NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h13H,5-12H2,1-4H3/t13-/m1/s1
InChI KeyCXTATJFJDMJMIY-CYBMUJFWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00085 g/LALOGPS
logP-1.2ALOGPS
logP-1.5ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.27 m³·mol⁻¹ChemAxon
Polarizability33.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+173.60930932474
DeepCCS[M-H]-171.25130932474
DeepCCS[M-2H]-204.13430932474
DeepCCS[M+Na]+180.17530932474
AllCCS[M+H]+177.232859911
AllCCS[M+H-H2O]+174.532859911
AllCCS[M+NH4]+179.732859911
AllCCS[M+Na]+180.432859911
AllCCS[M-H]-179.232859911
AllCCS[M+Na-2H]-180.332859911
AllCCS[M+HCOO]-181.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OctanoylcarnitineCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C2909.6Standard polar33892256
OctanoylcarnitineCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C1720.4Standard non polar33892256
OctanoylcarnitineCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C1975.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Octanoylcarnitine,1TMS,isomer #1CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C2013.7Semi standard non polar33892256
Octanoylcarnitine,1TBDMS,isomer #1CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C2237.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Octanoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octanoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octanoylcarnitine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octanoylcarnitine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Octanoylcarnitine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-6090000000-f5427438c18b619c6d122012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octanoylcarnitine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-9000000000-0ffd63a09867f6b170e52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octanoylcarnitine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000i-9000000000-558ce1fa555823e954792012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octanoylcarnitine 10V, Positive-QTOFsplash10-000i-0090000000-9c0281b8f2959b51e65e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octanoylcarnitine 20V, Positive-QTOFsplash10-000i-9050000000-5fd4264c445d0a0351132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octanoylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.23 +/- 0.08 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.121 +/- 0.009 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.17-0.50 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<0.22 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.21(0.06) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.18 +/- 0.07 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.17-0.50 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.061 (0.006-0.127) uMChildren (1-13 years old)BothNormal details
FecesDetected and Quantified0-4871.343 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected and Quantified0.74 +/- 0.32 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified1.1 +/- 0.52 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified60.81 +/- 2.32 umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified0.02-0.31 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.05(0.02-0.37) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0.04(0.02-0.09) umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected and Quantified0.05 (0.03-0.09) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.086 +/- 0.006 uMAdult (>18 years old)BothCeliac disease details
BloodDetected and Quantified0.37 uMAdolescent (13-18 years old)Male
Glutaric aciduria II
details
BloodDetected and Quantified0.59 uMAdolescent (13-18 years old)MaleGlutaric aciduria II details
BloodDetected and Quantified0.0943 (0.04369) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.26(0.08) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified0.1304 (0.0496) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified0.025 (0.014-0.034) uMAdult (>18 years old)BothVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD) details
BloodDetected and Quantified0.140 +/- 0.033 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.160 +/- 0.069 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
FecesDetected and Quantified0-11899.994 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
UrineDetected and Quantified69.63 +/- 2.32 umol/mmol creatinineAdolescent (13-18 years old)Both
Obese
details
UrineDetected and Quantified14.246-418.887 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedMedium Chain Acyl-CoA Dehydrogenase Deficiency details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]
  2. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
  1. Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Glutaric aciduria II
  1. Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. Duran M, De Klerk JB, Wadman SK, Bruinvis L, Ketting D: The differential diagnosis of dicarboxylic aciduria. J Inherit Metab Dis. 1984;7 Suppl 1:48-51. [PubMed:6434845 ]
Obesity
  1. Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
  2. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022246
KNApSAcK IDNot Available
Chemspider ID10128115
KEGG Compound IDC02838
BioCyc IDL-OCTANOYLCARNITINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11953814
PDB IDNot Available
ChEBI ID18102
Food Biomarker OntologyNot Available
VMH IDC8CRN
MarkerDB IDMDB00000253
Good Scents IDNot Available
References
Synthesis ReferenceDuhr, Edward F.; Mauro, J. Matthew; Clennan, Edward L.; Barden, Roland E. The synthesis and biological activity of thiolcarnitine and its thiolesters. Lipids (1983), 18(5), 382-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chace DH, DiPerna JC, Adam BW, Hannon WH: Errors caused by the use of D,L-octanoylcarnitine for blood-spot calibrators. Clin Chem. 2001 Apr;47(4):758-60. [PubMed:11274033 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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
Reactions
Octanoyl-CoA + L-Carnitine → Coenzyme A + Octanoylcarnitinedetails