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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:31:55 UTC
HMDB IDHMDB0000827
Secondary Accession Numbers
  • HMDB00827
Metabolite Identification
Common NameStearic acid
DescriptionStearic acid, also known as octadecanoic acid or C18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid (its ester is called stearate) is a saturated fatty acid that has 18 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. It exists as a waxy solid. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks, up to the 16-carbon palmitate, via the enzyme complex fatty acid synthase (FA synthase), at which point a fatty acid elongase is needed to further lengthen it. After synthesis, there are a variety of reactions it may undergo, including desaturation to oleate via stearoyl-CoA desaturase (PMID: 16477801 ). Stearic acid is found in all living organisms ranging from bacteria to plants to animals. It is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. For example, it is a component of cocoa butter and shea butter. It is used as a food additive, in cleaning and personal care products, and in lubricants. Its name comes from the Greek word stear, which means ‘tallow’ or ‘hard fat’.
Structure
Data?1582752159
Synonyms
ValueSource
18:0ChEBI
Acide octadecanoiqueChEBI
Acide steariqueChEBI
C18:0ChEBI
CH3-[CH2]16-COOHChEBI
N-Octadecanoic acidChEBI
OctadecansaeureChEBI
Octadecoic acidChEBI
OktadekansaeureChEBI
StearinsaeureChEBI
StearateKegg
N-OctadecanoateGenerator
OctadecoateGenerator
Octadecanoic acidHMDB
OctadecanoateHMDB
1-HeptadecanecarboxylateHMDB
1-Heptadecanecarboxylic acidHMDB
Stearex beadsHMDB
Stearic acid cherryHMDB
StearophanateHMDB
Stearophanic acidHMDB
Calcium stearateHMDB
Aluminum tristearateHMDB
Ammonium stearateHMDB
Zinc stearateHMDB
Magnesium stearateHMDB
Sodium stearateHMDB
Aluminum monostearateHMDB
FA(18:0)HMDB
Chemical FormulaC18H36O2
Average Molecular Weight284.4772
Monoisotopic Molecular Weight284.271530396
IUPAC Nameoctadecanoic acid
Traditional Namestearic acid
CAS Registry Number57-11-4
SMILES
CCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)
InChI KeyQIQXTHQIDYTFRH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point68.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0006 mg/mLNot Available
LogP8.23SANGSTER (1993)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg174.42330932474
[M-H]-Not Available176.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000220
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.6e-05 g/LALOGPS
logP10(8.02) g/LALOGPS
logP10(7.15) g/LChemAxon
logS10(-6.6) g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity86.29 m³·mol⁻¹ChemAxon
Polarizability38.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.84331661259
DarkChem[M+H]+175.84331661259
DarkChem[M-H]-174.90531661259
DarkChem[M-H]-174.90531661259
AllCCS[M+H]+182.31732859911
AllCCS[M-H]-179.01732859911
DeepCCS[M+H]+174.33730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Stearic acidCCCCCCCCCCCCCCCCCC(O)=O3131.5Standard polar33892256
Stearic acidCCCCCCCCCCCCCCCCCC(O)=O2120.6Standard non polar33892256
Stearic acidCCCCCCCCCCCCCCCCCC(O)=O2175.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Stearic acid,1TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C2242.3Semi standard non polar33892256
Stearic acid,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2496.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Stearic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0159-1900000000-9cc966384906cd35537d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stearic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0900000000-b87a9955374d11966ba62014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stearic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0100-9700000000-979da356343fa06979932014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stearic acid GC-MS (1 TMS)splash10-0159-2901000000-16194c704b7abd1936472014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stearic acid EI-B (Non-derivatized)splash10-06yo-9110000000-6f345827577cdc861aca2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stearic acid EI-B (Non-derivatized)splash10-075c-9220000000-207b53a511763954eb662017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stearic acid GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-9cc966384906cd35537d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stearic acid GC-EI-TOF (Non-derivatized)splash10-0159-0900000000-b87a9955374d11966ba62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stearic acid GC-EI-TOF (Non-derivatized)splash10-0100-9700000000-979da356343fa06979932017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stearic acid GC-MS (Non-derivatized)splash10-0159-2901000000-16194c704b7abd1936472017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stearic acid GC-EI-TOF (Non-derivatized)splash10-014i-1900000000-d34fc01a79cc27a320802017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stearic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9540000000-c6c002443ac3a40dabdb2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stearic acid GC-MS (1 TMS) - 70eV, Positivesplash10-009l-9551000000-b9a196da32e6273fad4f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stearic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stearic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stearic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0c03-9200000000-5dd52f837d56d80fa9682014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-001i-0090000000-1368043827a20e28c1722012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-001i-0090000000-5c3fa1d38cf3d0a38d742012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid ESI-TOF 10V, Negative-QTOFsplash10-004r-0791000000-10ab351997f48e5126572017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid ESI-TOF , Negative-QTOFsplash10-004r-0791000000-10ab351997f48e5126572017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid ESI-TOF 20V, Negative-QTOFsplash10-004r-0791000000-10ab351997f48e5126572017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid ESI-TOF 30V, Negative-QTOFsplash10-001i-0090000000-55efcdc9c7bfd521ef5a2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid ESI-TOF 10V, Negative-QTOFsplash10-001i-0090000000-9441e6362046ae1983842017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid ESI-TOF , Negative-QTOFsplash10-001i-0090000000-f629b105972a0728beb62017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid ESI-TOF 20V, Negative-QTOFsplash10-001i-0090000000-fbf3f8e91badb0ec251d2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid ESI-TOF 30V, Negative-QTOFsplash10-001i-0090000000-55efcdc9c7bfd521ef5a2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid LC-ESI-IT , negative-QTOFsplash10-00lr-0090000000-a702a9f469dbb513856a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid LC-ESI-TOF , negative-QTOFsplash10-001i-0090000000-9441e6362046ae1983842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearic acid LC-ESI-TOF , negative-QTOFsplash10-001i-0090000000-fbf3f8e91badb0ec251d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 10V, Positive-QTOFsplash10-014r-0090000000-34a309d09cb2def46a192015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 20V, Positive-QTOFsplash10-00kr-4690000000-f68e827f7ebccd80d5bf2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 40V, Positive-QTOFsplash10-052f-8920000000-2e865f09d760af582c072015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 10V, Positive-QTOFsplash10-014r-0090000000-34a309d09cb2def46a192015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 20V, Positive-QTOFsplash10-00kr-4690000000-f68e827f7ebccd80d5bf2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 40V, Positive-QTOFsplash10-052f-8920000000-2e865f09d760af582c072015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 10V, Negative-QTOFsplash10-001i-0090000000-b3ce35f839a30b41c7182015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 20V, Negative-QTOFsplash10-00m0-1090000000-bbb339a3dbe1b9ba0d542015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 40V, Negative-QTOFsplash10-0a4l-9240000000-1b84b49819fa37fce1ae2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 10V, Negative-QTOFsplash10-001i-0090000000-b3ce35f839a30b41c7182015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 20V, Negative-QTOFsplash10-00m0-1090000000-bbb339a3dbe1b9ba0d542015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearic acid 40V, Negative-QTOFsplash10-0a4l-9240000000-1b84b49819fa37fce1ae2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Adipose Tissue
  • Brain
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified85 (31-470) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified48.8 +/- 21 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified41.119 +/- 5.521 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.90-13.5 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified8.70-13.3 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified467.524 +/- 38.667 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified460.494 +/- 31.637 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified460.494 +/- 35.152 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified464.00907 +/- 35.152 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified57 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified60 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified73 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified78 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified232 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified261 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified707.790 +/- 164.407 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified585.741 +/- 101.871 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified830 +/- 160 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified770 +/- 110 uMAdult (>18 years old)MaleNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified22.1 +/- 0.035 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified10.0 +/- 10.0 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified71.429 +/- 129.114 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified44.995 +/- 75.226 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified6.88 +/- 1.23 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.36 +/- 2.82 umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected and Quantified18.703 +/- 7.698 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.32-0.82 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.9 (1.6-6.6) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.10 +/- 0.03 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0-4.1 umol/mmol creatinineInfant (0-1 year old)Male
Normal
details
UrineDetected and Quantified0-6.5 umol/mmol creatinineInfant (0-1 year old)Male
Normal
details
UrineDetected and Quantified0-6.61 umol/mmol creatinineInfant (0-1 year old)Female
Normal
details
UrineDetected and Quantified0-9.75 umol/mmol creatinineInfant (0-1 year old)Female
Normal
details
UrineDetected and Quantified0.35-0.50 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified3.9(2.3-7.7) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Breast cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIron deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCCD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIleal Crohn's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified26.428 +/- 22.351 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified33.059 +/- 25.405 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Lv W, Yang T: Identification of possible biomarkers for breast cancer from free fatty acid profiles determined by GC-MS and multivariate statistical analysis. Clin Biochem. 2012 Jan;45(1-2):127-33. doi: 10.1016/j.clinbiochem.2011.10.011. Epub 2011 Oct 26. [PubMed:22061338 ]
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
  2. Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Crohn's disease
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Iron deficiency
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. 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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB03193
Phenol Explorer Compound IDNot Available
FooDB IDFDB031183
KNApSAcK IDC00001238
Chemspider ID5091
KEGG Compound IDC01530
BioCyc IDSTEARIC_ACID
BiGG ID37799
Wikipedia LinkStearic_acid
METLIN ID189
PubChem Compound5281
PDB IDNot Available
ChEBI ID28842
Food Biomarker OntologyNot Available
VMH IDOCDCA
MarkerDB IDMDB00000263
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  2. Crocker I, Lawson N, Daniels I, Baker P, Fletcher J: Significance of fatty acids in pregnancy-induced immunosuppression. Clin Diagn Lab Immunol. 1999 Jul;6(4):587-93. [PubMed:10391868 ]
  3. Katsuta Y, Iida T, Inomata S, Denda M: Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. J Invest Dermatol. 2005 May;124(5):1008-13. [PubMed:15854043 ]
  4. Sanjurjo P, Rodriguez-Alarcon J, Rodriguez-Soriano J: Plasma fatty acid composition during the first week of life following feeding with human milk or formula. Acta Paediatr Scand. 1988 Mar;77(2):202-6. [PubMed:3354331 ]
  5. Neoptolemos JP, Thomas BS: Erythrocyte membrane stearic acid: oleic acid ratios in colorectal cancer using tube capillary column gas liquid chromatography. Ann Clin Biochem. 1990 Jan;27 ( Pt 1):38-43. [PubMed:2310156 ]
  6. Turpeinen AM, Wubert J, Aro A, Lorenz R, Mutanen M: Similar effects of diets rich in stearic acid or trans-fatty acids on platelet function and endothelial prostacyclin production in humans. Arterioscler Thromb Vasc Biol. 1998 Feb;18(2):316-22. [PubMed:9484999 ]
  7. Daubresse JC: [Atherosclerosis and nutrition]. Rev Med Brux. 2000 Sep;21(4):A359-62. [PubMed:11068494 ]
  8. Hoppu U, Rinne M, Lampi AM, Isolauri E: Breast milk fatty acid composition is associated with development of atopic dermatitis in the infant. J Pediatr Gastroenterol Nutr. 2005 Sep;41(3):335-8. [PubMed:16131990 ]
  9. Musial W, Kubis A: Preliminary assessment of alginic acid as a factor buffering triethanolamine interacting with artificial skin sebum. Eur J Pharm Biopharm. 2003 Mar;55(2):237-40. [PubMed:12637103 ]
  10. Doran TA, Ford JA, Allen LC, Wong PY, Benzie RJ: Amniotic fluid lecithin/sphingomyelin ratio, palmitic acid, palmitic acid/stearic acid ratio, total cortisol, creatinine, and percentage of lipid-positive cells in assessment of fetal maturity and fetal pulmonary maturity: a comparison. Am J Obstet Gynecol. 1979 Feb 1;133(3):302-7. [PubMed:433991 ]
  11. Kazmierczak SC, Gurachevsky A, Matthes G, Muravsky V: Electron spin resonance spectroscopy of serum albumin: a novel new test for cancer diagnosis and monitoring. Clin Chem. 2006 Nov;52(11):2129-34. Epub 2006 Sep 21. [PubMed:16990414 ]
  12. Kelly FD, Sinclair AJ, Mann NJ, Turner AH, Abedin L, Li D: A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males. Eur J Clin Nutr. 2001 Feb;55(2):88-96. [PubMed:11305631 ]
  13. Diani F, Cacco M, Molinaroli A, Cerruti G, Meloncelli C, Turinetto A: [Fatty acid composition of the cervical mucus obtained during ovulation and at the term of pregnancy]. Minerva Ginecol. 1998 Oct;50(10):405-10. [PubMed:9866950 ]
  14. 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 ]
  15. Sampath H, Ntambi JM: The fate and intermediary metabolism of stearic acid. Lipids. 2005 Dec;40(12):1187-91. doi: 10.1007/s11745-005-1484-z. [PubMed:16477801 ]

Only showing the first 10 proteins. There are 72 proteins in total.

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in sugar binding
Specific function:
Has lysophospholipase activity.
Gene Name:
LGALS13
Uniprot ID:
Q9UHV8
Molecular weight:
16118.44
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Molecular weight:
21066.99
General function:
Involved in metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635

Transporters

General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:
SLC27A1
Uniprot ID:
Q6PCB7
Molecular weight:
71107.5

Only showing the first 10 proteins. There are 72 proteins in total.