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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:44:29 UTC
Update Date2022-03-07 03:17:53 UTC
HMDB IDHMDB0062336
Secondary Accession Numbers
  • HMDB62336
Metabolite Identification
Common NameN-Oleoyl phenylalanine
DescriptionN-oleoyl phenylalanine, also known as oleoyl-L-phe-OH belongs to the class of compounds known as N-acylamides. These are molecules characterized by a fatty acyl group linked to a primary amine by an amide bond. More specifically, it is an Oleic acid amide of Phenylalanine. It is believed that there are more than 800 types of N-acylamides in the human body. N-acylamides fall into several categories: amino acid conjugates (e.g., those acyl amides conjugated with amino acids), neurotransmitter conjugates (e.g., those acylamides conjugated with neurotransmitters), ethanolamine conjugates (e.g., those acylamides conjugated to ethanolamine), and taurine conjugates (e.g., those acyamides conjugated to taurine). N-Oleoyl phenylalanine is an amino acid conjugate. N-acylamides can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain N-acylamides; 2) medium-chain N-acylamides; 3) long-chain N-acylamides; and 4) very long-chain N-acylamides; 5) hydroxy N-acylamides; 6) branched chain N-acylamides; 7) unsaturated N-acylamides; 8) dicarboxylic N-acylamides and 9) miscellaneous N-acylamides. N-Oleoyl phenylalanine is therefore classified as a long chain N-acylamide. N-acyl amides have a variety of signaling functions in physiology, including in cardiovascular activity, metabolic homeostasis, memory, cognition, pain, motor control and others (PMID: 15655504 ). N-acyl amides have also been shown to play a role in cell migration, inflammation and certain pathological conditions such as diabetes, cancer, neurodegenerative disease, and obesity (PMID: 23144998 ; PMID: 25136293 ; PMID: 28854168 ).N-acyl amides can be synthesized both endogenously and by gut microbiota (PMID: 28854168 ). N-acylamides can be biosynthesized via different routes, depending on the parent amine group. N-acyl ethanolamines (NAEs) are formed via the hydrolysis of an unusual phospholipid precursor, N-acyl-phosphatidylethanolamine (NAPE), by a specific phospholipase D. N-acyl amino acids are synthesized via a circulating peptidase M20 domain containing 1 (PM20D1), which can catalyze the bidirectional the condensation and hydrolysis of a variety of N-acyl amino acids. The degradation of N-acylamides is largely mediated by an enzyme called fatty acid amide hydrolase (FAAH), which catalyzes the hydrolysis of N-acylamides into fatty acids and the biogenic amines. Many N-acylamides are involved in lipid signaling system through interactions with transient receptor potential channels (TRP). TRP channel proteins interact with N-acyl amides such as N-arachidonoyl ethanolamide (Anandamide), N-arachidonoyl dopamine and others in an opportunistic fashion (PMID: 23178153 ). This signaling system has been shown to play a role in the physiological processes involved in inflammation (PMID: 25136293 ). Other N-acyl amides, including N-oleoyl-glutamine, have also been characterized as TRP channel antagonists (PMID: 29967167 ). N-acylamides have also been shown to have G-protein-coupled receptors (GPCRs) binding activity (PMID: 28854168 ). The study of N-acylamides is an active area of research and it is likely that many novel N-acylamides will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.
Structure
Data?1563866297
Synonyms
ValueSource
(2S)-2-[(9Z)-Octadec-9-enoylamino]-3-phenylpropanoic acidChEBI
(2S)-2-[(9Z)-Octadec-9-enoylamino]-3-phenylpropionic acidChEBI
N-(9Z-Octadecenoyl)-phenylalanineChEBI
N-Oleoyl phenylalanineChEBI
Oleoyl-L-phe-OHChEBI
(2S)-2-[(9Z)-Octadec-9-enoylamino]-3-phenylpropanoateGenerator
(2S)-2-[(9Z)-Octadec-9-enoylamino]-3-phenylpropionateGenerator
Chemical FormulaC27H43NO3
Average Molecular Weight429.645
Monoisotopic Molecular Weight429.324294249
IUPAC Name(2S)-2-{[(9Z)-1-hydroxyoctadec-9-en-1-ylidene]amino}-3-phenylpropanoic acid
Traditional Name(2S)-2-{[(9Z)-1-hydroxyoctadec-9-en-1-ylidene]amino}-3-phenylpropanoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C27H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-26(29)28-25(27(30)31)23-24-20-17-16-18-21-24/h9-10,16-18,20-21,25H,2-8,11-15,19,22-23H2,1H3,(H,28,29)(H,30,31)/b10-9-/t25-/m0/s1
InChI KeyUWKNPULCJWBBDD-JRUKXMRZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.8e-05 g/lALOGPS
LogP7.82ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP7.79ALOGPS
logP8.72ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.18ChemAxon
pKa (Strongest Basic)1.59ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity129.84 m³·mol⁻¹ChemAxon
Polarizability52.87 ųChemAxon
Number of Rings1ChemAxon
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]+211.75731661259
DarkChem[M-H]-212.13231661259
DeepCCS[M+H]+223.23930932474
DeepCCS[M-H]-219.97930932474
DeepCCS[M-2H]-254.78830932474
DeepCCS[M+Na]+230.95530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Oleoyl phenylalanine[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=O4219.2Standard polar33892256
N-Oleoyl phenylalanine[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=O2865.3Standard non polar33892256
N-Oleoyl phenylalanine[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=O3300.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Oleoyl phenylalanine,1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O)O[Si](C)(C)C3314.6Semi standard non polar33892256
N-Oleoyl phenylalanine,1TMS,isomer #2CCCCCCCC/C=C\CCCCCCCC(O)=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C3263.8Semi standard non polar33892256
N-Oleoyl phenylalanine,2TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)O[Si](C)(C)C3264.2Semi standard non polar33892256
N-Oleoyl phenylalanine,1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O)O[Si](C)(C)C(C)(C)C3547.0Semi standard non polar33892256
N-Oleoyl phenylalanine,1TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCC(O)=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C3511.4Semi standard non polar33892256
N-Oleoyl phenylalanine,2TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3720.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Oleoyl phenylalanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9435000000-b989c1276e9cfd7fdf462017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Oleoyl phenylalanine GC-MS (2 TMS) - 70eV, Positivesplash10-0a4l-9210420000-31644219426086c65bbd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Oleoyl phenylalanine 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 - N-Oleoyl phenylalanine 40V, Negative-QTOFsplash10-03dl-4910000000-1f08cec7ebcc0c0452322021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Oleoyl phenylalanine 20V, Negative-QTOFsplash10-004i-0000900000-306e692649a9e6ca67142021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Oleoyl phenylalanine 10V, Negative-QTOFsplash10-004i-0000900000-4ace816025de05f331f82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Oleoyl phenylalanine 40V, Positive-QTOFsplash10-00di-1900000000-8f8574d3319f04e5fa112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Oleoyl phenylalanine 10V, Positive-QTOFsplash10-001i-0000900000-dce0d8e2b49db401e85e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Oleoyl phenylalanine 20V, Positive-QTOFsplash10-014i-0900100000-0c100cff41901f9a1aba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Oleoyl phenylalanine 40V, Positive-QTOFsplash10-03dl-4910000000-ff77dad3bb1b5c6f93e82021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 10V, Positive-QTOFsplash10-03e9-2912800000-3d614c41bb7531bdaad02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 20V, Positive-QTOFsplash10-02t9-1920000000-1f25a3c71127a1e76e8b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 40V, Positive-QTOFsplash10-01ox-9710000000-9a0a00d69d428b2df2572017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 10V, Negative-QTOFsplash10-004i-0002900000-dadf550a6489b2b294e22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 20V, Negative-QTOFsplash10-03gi-3797700000-b4ebcdb7f1172b36b6742017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 40V, Negative-QTOFsplash10-00kf-9430000000-fba1ff295e0c8bd38d6e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 10V, Positive-QTOFsplash10-0159-0941700000-47a6b923954230c892112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 20V, Positive-QTOFsplash10-014i-0910000000-f4da0df3d32fe28fdf162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 40V, Positive-QTOFsplash10-0fdk-3900000000-4f24808ce3d97153b4422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 10V, Negative-QTOFsplash10-004i-0200900000-35b0adc656329a8a9bb12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 20V, Negative-QTOFsplash10-004i-2620900000-b6cfcc9be4c5bf57dbce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Oleoyl phenylalanine 40V, Negative-QTOFsplash10-00ou-8913000000-4391bb156580cc48c5632021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922059
PDB IDNot Available
ChEBI ID134021
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bradshaw HB, Walker JM: The expanding field of cannabimimetic and related lipid mediators. Br J Pharmacol. 2005 Feb;144(4):459-65. doi: 10.1038/sj.bjp.0706093. [PubMed:15655504 ]
  2. Grapov D, Adams SH, Pedersen TL, Garvey WT, Newman JW: Type 2 diabetes associated changes in the plasma non-esterified fatty acids, oxylipins and endocannabinoids. PLoS One. 2012;7(11):e48852. doi: 10.1371/journal.pone.0048852. Epub 2012 Nov 8. [PubMed:23144998 ]
  3. Raboune S, Stuart JM, Leishman E, Takacs SM, Rhodes B, Basnet A, Jameyfield E, McHugh D, Widlanski T, Bradshaw HB: Novel endogenous N-acyl amides activate TRPV1-4 receptors, BV-2 microglia, and are regulated in brain in an acute model of inflammation. Front Cell Neurosci. 2014 Aug 1;8:195. doi: 10.3389/fncel.2014.00195. eCollection 2014. [PubMed:25136293 ]
  4. Cohen LJ, Esterhazy D, Kim SH, Lemetre C, Aguilar RR, Gordon EA, Pickard AJ, Cross JR, Emiliano AB, Han SM, Chu J, Vila-Farres X, Kaplitt J, Rogoz A, Calle PY, Hunter C, Bitok JK, Brady SF: Commensal bacteria make GPCR ligands that mimic human signalling molecules. Nature. 2017 Sep 7;549(7670):48-53. doi: 10.1038/nature23874. Epub 2017 Aug 30. [PubMed:28854168 ]
  5. Bradshaw HB, Raboune S, Hollis JL: Opportunistic activation of TRP receptors by endogenous lipids: exploiting lipidomics to understand TRP receptor cellular communication. Life Sci. 2013 Mar 19;92(8-9):404-9. doi: 10.1016/j.lfs.2012.11.008. Epub 2012 Nov 20. [PubMed:23178153 ]
  6. Long JZ, Roche AM, Berdan CA, Louie SM, Roberts AJ, Svensson KJ, Dou FY, Bateman LA, Mina AI, Deng Z, Jedrychowski MP, Lin H, Kamenecka TM, Asara JM, Griffin PR, Banks AS, Nomura DK, Spiegelman BM: Ablation of PM20D1 reveals N-acyl amino acid control of metabolism and nociception. Proc Natl Acad Sci U S A. 2018 Jul 17;115(29):E6937-E6945. doi: 10.1073/pnas.1803389115. Epub 2018 Jul 2. [PubMed:29967167 ]