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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2022-07-14 22:35:49 UTC
HMDB IDHMDB0002088
Secondary Accession Numbers
  • HMDB02088
Metabolite Identification
Common NameOleoylethanolamide
DescriptionOleoylethanolamide (OEA or NOE) is an N-acylethanolamine. N-Acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation have been attributed to a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. Oleoylethanolamide is an inhibitor of the sphingolipid signalling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). Oleoylethanolamide blocks the effects of TNF and arachidonic acid on intracellular Ca concentration (PMID: 12692337 , 12056855 , 12560208 , 11997249 ). Oleoylethanolamide is related to the endocannabinoid anandamide. Endocannabinoids signal through cannabinoid receptors (also stimulated by the active ingredient of cannabis) but although related in structure, synthesis, and degradation to anandamide, OEA cannot be considered an endocannabinoid as it does not activate the cannabinoid receptors. Most of the reported responses to OEA can be attributed to the activation of peroxisome proliferator-activated receptor-alpha (PPAR-alpha). Administration of OEA inhibits body weight gain in rats. In adipocytes and hepatocytes, OEA inhibits mitogenic and metabolic signalling by the insulin receptor and produces glucose intolerance. It also inhibits gastric emptying, which might act together with the sensory neuronal signals to achieve satiety. OEA is permanently elevated in diabetic obese patients. OEA also reduces visceral and inflammatory responses through a PPAR-alpha-activation independent mechanism (PMID: 17449181 ). OEA is an antagonist of TRVP1 (the transient receptor potential vanilloid type 1 receptor). Overall, OEA has beneficial effects on health by inducing food intake control, lipid beta-oxidation, body weight loss and analgesic effects (PMID: 18704536 ).
Structure
Data?1657838149
Synonyms
ValueSource
N-(2-Hydroxyethyl)-9-octadecenamideChEBI
N-(2-Hydroxyethyl)oleamideChEBI
N-(9Z-Octadecenoyl) ethanolamineChEBI
N-(9Z-Octadecenoyl)-ethanolamineChEBI
N-(cis-9-Octadecenoyl) ethanolamineChEBI
N-(Hydroxyethyl)oleamideChEBI
N-Oleoyl ethanolamineChEBI
N-OleoylethanolamineChEBI
OEAChEBI
Oleamide meaChEBI
Oleoyl 1-ethanolamideChEBI
Oleoyl monoethanolamideChEBI
N-Oleoyl ethanolamine, oleoyl monoethanolamide, oleoylethanolamideHMDB
N-Oleoyl-2-aminoethanolHMDB
NOEHMDB
Oleic acid ethanolamideHMDB
Oleic acid monoethanolamideHMDB
N-OEAHMDB
(9Z)-N-(2-Hydroxyethyl)-9-octadecenamideHMDB
N-(2-Hydroxyethyl)-9-Z-octadecenamideHMDB
N-OleoylethanolamideHMDB
Oleoyl ethanolamideHMDB
OleoylethanolamineHMDB
OleoylethanolamideChEBI
AEA(18:1)HMDB
Acylethanolamine 18:1HMDB
Chemical FormulaC20H39NO2
Average Molecular Weight325.5292
Monoisotopic Molecular Weight325.298079497
IUPAC Name(9Z)-N-(2-hydroxyethyl)octadec-9-enamide
Traditional Nameoleoylethanolamide
CAS Registry Number111-58-0
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)NCCO
InChI Identifier
InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
InChI KeyBOWVQLFMWHZBEF-KTKRTIGZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentN-acylethanolamines
Alternative Parents
Substituents
  • N-acylethanolamine
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point496.35 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.069 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.406 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00024 g/LALOGPS
logP6.74ALOGPS
logP5.51ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)15.47ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity100.41 m³·mol⁻¹ChemAxon
Polarizability42.77 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.38631661259
DarkChem[M-H]-186.85231661259
DeepCCS[M+H]+190.7130932474
DeepCCS[M-H]-188.1630932474
DeepCCS[M-2H]-221.88830932474
DeepCCS[M+Na]+198.17830932474
AllCCS[M+H]+190.432859911
AllCCS[M+H-H2O]+187.832859911
AllCCS[M+NH4]+192.832859911
AllCCS[M+Na]+193.532859911
AllCCS[M-H]-188.432859911
AllCCS[M+Na-2H]-190.332859911
AllCCS[M+HCOO]-192.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OleoylethanolamideCCCCCCCC\C=C/CCCCCCCC(=O)NCCO3025.5Standard polar33892256
OleoylethanolamideCCCCCCCC\C=C/CCCCCCCC(=O)NCCO2523.5Standard non polar33892256
OleoylethanolamideCCCCCCCC\C=C/CCCCCCCC(=O)NCCO2689.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oleoylethanolamide,1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C2720.7Semi standard non polar33892256
Oleoylethanolamide,1TMS,isomer #2CCCCCCCC/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C2686.5Semi standard non polar33892256
Oleoylethanolamide,2TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2729.4Semi standard non polar33892256
Oleoylethanolamide,2TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2749.1Standard non polar33892256
Oleoylethanolamide,2TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2686.6Standard polar33892256
Oleoylethanolamide,1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C2944.4Semi standard non polar33892256
Oleoylethanolamide,1TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C2900.5Semi standard non polar33892256
Oleoylethanolamide,2TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3186.2Semi standard non polar33892256
Oleoylethanolamide,2TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3068.7Standard non polar33892256
Oleoylethanolamide,2TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2874.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oleoylethanolamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fdn-9880000000-505c4b2acd75d00c6b4c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleoylethanolamide GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9442000000-7630c4851b93798913892017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleoylethanolamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleoylethanolamide LC-ESI-qTof , Positive-QTOFsplash10-0592-2950000000-3a4675ee36a05c78c6da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleoylethanolamide , positive-QTOFsplash10-0a4i-6924100000-697643f4a75f68f277952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleoylethanolamide 20V, Positive-QTOFsplash10-03di-9003000000-5932d86ac015014b45b72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleoylethanolamide 10V, Positive-QTOFsplash10-004i-0009000000-39f5348b2f2f84a7bcfb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleoylethanolamide 40V, Positive-QTOFsplash10-03xr-9000000000-e33bcdecef98696ee3b22021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 10V, Positive-QTOFsplash10-01t9-5149000000-4df23e68e6a0912a6bbc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 20V, Positive-QTOFsplash10-03dl-9221000000-c242848558751b6659582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 40V, Positive-QTOFsplash10-01ox-9410000000-af2a86c6d06cfb4d91d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 10V, Negative-QTOFsplash10-00di-0029000000-6deda61377943259bcf32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 20V, Negative-QTOFsplash10-074l-8079000000-82821facf1a599eef9182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 40V, Negative-QTOFsplash10-0006-9010000000-332b31d63933e6f4814c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 10V, Negative-QTOFsplash10-00di-0019000000-0c1e6ede8b9b256d884e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 20V, Negative-QTOFsplash10-00di-5129000000-136f2e581bc92cd24c652021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 40V, Negative-QTOFsplash10-06r6-9010000000-cf7558f653e48ef28f6b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 10V, Positive-QTOFsplash10-01t9-8019000000-52e109ae1a8827f24f152021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 20V, Positive-QTOFsplash10-03dl-9000000000-fbcb31079417201e66cb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylethanolamide 40V, Positive-QTOFsplash10-01ox-9000000000-c882967afa3654d663752021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0036 +/- 0.00068 uMAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified46.8 +/- 34 uMAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022839
KNApSAcK IDNot Available
Chemspider ID4446574
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOleoylethanolamide
METLIN IDNot Available
PubChem Compound5283454
PDB IDNot Available
ChEBI ID71466
Food Biomarker OntologyNot Available
VMH IDOLETH
MarkerDB IDNot Available
Good Scents IDrw1301731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hofmann U, Domeier E, Frantz S, Laser M, Weckler B, Kuhlencordt P, Heuer S, Keweloh B, Ertl G, Bonz AW: Increased myocardial oxygen consumption by TNF-alpha is mediated by a sphingosine signaling pathway. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2100-5. Epub 2003 Jan 30. [PubMed:12560208 ]
  2. Tripathy S, Kleppinger-Sparace K, Dixon RA, Chapman KD: N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein. Plant Physiol. 2003 Apr;131(4):1781-91. [PubMed:12692337 ]
  3. Lecour S, Smith RM, Woodward B, Opie LH, Rochette L, Sack MN: Identification of a novel role for sphingolipid signaling in TNF alpha and ischemic preconditioning mediated cardioprotection. J Mol Cell Cardiol. 2002 May;34(5):509-18. [PubMed:12056855 ]
  4. Amadou A, Nawrocki A, Best-Belpomme M, Pavoine C, Pecker F: Arachidonic acid mediates dual effect of TNF-alpha on Ca2+ transients and contraction of adult rat cardiomyocytes. Am J Physiol Cell Physiol. 2002 Jun;282(6):C1339-47. [PubMed:11997249 ]
  5. Suardiaz M, Estivill-Torrus G, Goicoechea C, Bilbao A, Rodriguez de Fonseca F: Analgesic properties of oleoylethanolamide (OEA) in visceral and inflammatory pain. Pain. 2007 Dec 15;133(1-3):99-110. Epub 2007 Apr 20. [PubMed:17449181 ]
  6. Thabuis C, Tissot-Favre D, Bezelgues JB, Martin JC, Cruz-Hernandez C, Dionisi F, Destaillats F: Biological functions and metabolism of oleoylethanolamide. Lipids. 2008 Oct;43(10):887-94. doi: 10.1007/s11745-008-3217-y. Epub 2008 Aug 13. [PubMed:18704536 ]
  7. 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 ]
  8. Anton M, Rodriguez-Gonzalez A, Rodriguez-Rojo IC, Pastor A, Correas A, Serrano A, Ballesta A, Alen F, Gomez de Heras R, de la Torre R, Rodriguez de Fonseca F, Orio L: Increased plasma oleoylethanolamide and palmitoleoylethanolamide levels correlate with inflammatory changes in alcohol binge drinkers: the case of HMGB1 in women. Addict Biol. 2018 Nov;23(6):1242-1250. doi: 10.1111/adb.12580. Epub 2017 Nov 27. [PubMed:29178411 ]

Enzymes

General function:
Involved in ceramidase activity
Specific function:
Hydrolyzes the sphingolipid ceramide into sphingosine and free fatty acid at an optimal pH of 6.5-8.5. Acts as a key regulator of sphingolipid signaling metabolites by generating sphingosine at the cell surface. Acts as a repressor of apoptosis both by reducing C16-ceramide, thereby preventing ceramide-induced apoptosis, and generating sphingosine, a precursor of the antiapoptotic factor sphingosine 1-phosphate. Probably involved in the digestion of dietary sphingolipids in intestine by acting as a key enzyme for the catabolism of dietary sphingolipids and regulating the levels of bioactive sphingolipid metabolites in the intestinal tract.
Gene Name:
ASAH2
Uniprot ID:
Q9NR71
Molecular weight:
19024.55
References
  1. Hofmann U, Domeier E, Frantz S, Laser M, Weckler B, Kuhlencordt P, Heuer S, Keweloh B, Ertl G, Bonz AW: Increased myocardial oxygen consumption by TNF-alpha is mediated by a sphingosine signaling pathway. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2100-5. Epub 2003 Jan 30. [PubMed:12560208 ]