N-oleoyl leucine
PubChem CID
52922067
Structure
Molecular Formula
Synonyms
- N-oleoyl leucine
- 136560-76-4
- oleoyl-L-leucine
- N-Oleyl-Leucine
- N-(9Z-octadecenoyl)-leucine
Molecular Weight
395.6 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
- Create:2011-06-09
- Modify:2025-01-11
Description
N-oleoyl-L-leucine is an L-leucine derivative resulting from the formal condensation of the carboxy group of oleic acid with the amino group of L-leucine. It is a L-leucine derivative and a N-(fatty acyl)-L-alpha-amino acid. It is functionally related to an oleic acid. It is a conjugate acid of a N-oleoyl-L-leucinate.
Chemical Structure Depiction
Conformer generation is disallowed since too flexible
SVG Image
IUPAC Condensed
oleoyl-Leu-OH
Sequence
L
HELM
PEPTIDE1{[CCCCCCCC/C=C\CCCCCCCC(=O)N[C@@H](CC(C)C)C(=O)O]}$$$$
IUPAC
N-oleoyl-L-leucine
(2S)-4-methyl-2-[[(Z)-octadec-9-enoyl]amino]pentanoic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)
InChI=1S/C24H45NO3/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)25-22(24(27)28)20-21(2)3/h11-12,21-22H,4-10,13-20H2,1-3H3,(H,25,26)(H,27,28)/b12-11-/t22-/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)
UMOAAMQGRRCHPA-GJCOWUBNSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)
CCCCCCCC/C=C\CCCCCCCC(=O)N[C@@H](CC(C)C)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C24H45NO3
Computed by PubChem 2.1 (PubChem release 2019.06.18)
136560-76-4
- N-oleoyl leucine
- 136560-76-4
- oleoyl-L-leucine
- N-Oleyl-Leucine
- N-(9Z-octadecenoyl)-leucine
- CHEMBL4228560
- (2S)-4-methyl-2-[[(Z)-octadec-9-enoyl]amino]pentanoic acid
- N-[(9Z)-1-oxo-9-octadecen-1-yl]-L-leucine
- N-(9Z-octadecenoyl)-L-leucine
- oleoylleucine
- N-oleoylleucine
- N-Oleoyl-L-leucine
- N-[(9Z)-octadecenoyl]leucine
- SCHEMBL15285296
- CHEBI:136616
- DTXSID801347277
- N-[(9Z)-octadecenoyl]-L-leucine
- BDBM50537017
- LMFA08020116
- AKOS040754833
- HY-120731
- N(2)-[(9Z)-octadec-9-enoyl]-L-leucine
- CS-0078917
- Q63395253
- (2S)-4-methyl-2-{[(9Z)-octadec-9-enoyl]amino}pentanoic acid
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
395.6 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
8.3
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
19
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
395.33994430 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
395.33994430 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
66.4 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
28
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
418
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)
Fatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl amino acids [FA0805]
Accession ID
Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
7.227 min
Precursor m/z
396.3472
Precursor Adduct
[M+H]+
Top 5 Peaks
396.3476 999
86.0959 46
132.1018 41
398.3535 34
378.3369 24
License
CC BY
Accession ID
Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
7.227 min
Precursor m/z
396.3472
Precursor Adduct
[M+H]+
Top 5 Peaks
86.0959 999
132.1018 242
396.3474 136
350.3416 65
265.2528 30
License
CC BY
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=UMOAAMQGRRCHPA-GJCOWUBNSA-N
- ChEBIN-oleoyl-L-leucinehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:136616
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- EPA DSSToxN-Oleyl-Leucinehttps://comptox.epa.gov/dashboard/DTXSID801347277
- LIPID MAPSLipid Classificationhttps://www.lipidmaps.org/
- MassBank Europe
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- Metabolomics Workbench
- PharosLICENSEData accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.https://pharos.nih.gov/about(2S)-4-Methyl-2-[[(Z)-octadec-9-enoyl]amino]pentanoic Acidhttps://pharos.nih.gov/ligands/2KPQTP9M9CZL
- Springer Nature
- WikidataN-oleoyl-L-leucinehttps://www.wikidata.org/wiki/Q63395253
- PubChem
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 395238953https://pubchem.ncbi.nlm.nih.gov/substance/395238953
CONTENTS