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N-oleoyl leucine

PubChem CID
52922067
Structure
N-oleoyl leucine_small.png
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.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-oleoyl leucine.png

1.2 3D Status

Conformer generation is disallowed since too flexible

2 Biologic Description

SVG Image
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

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2S)-4-methyl-2-[[(Z)-octadec-9-enoyl]amino]pentanoic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

3.1.2 InChI

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)

3.1.3 InChIKey

UMOAAMQGRRCHPA-GJCOWUBNSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.4 SMILES

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)

3.2 Molecular Formula

C24H45NO3
Computed by PubChem 2.1 (PubChem release 2019.06.18)

3.3 Other Identifiers

3.3.1 CAS

136560-76-4

3.3.2 ChEBI ID

3.3.3 ChEMBL ID

3.3.4 DSSTox Substance ID

3.3.5 Lipid Maps ID (LM_ID)

3.3.6 Metabolomics Workbench ID

3.3.7 Pharos Ligand ID

3.3.8 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

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)

4.2 Chemical Classes

4.2.1 Lipids

Fatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl amino acids [FA0805]

5 Spectral Information

5.1 Mass Spectrometry

5.1.1 LC-MS

1 of 9
View All
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

Thumbnail
Thumbnail
License
CC BY
2 of 9
View All
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

Thumbnail
Thumbnail
License
CC BY

7 Chemical Vendors

8 Literature

8.1 Consolidated References

8.2 Springer Nature References

8.3 Chemical Co-Occurrences in Literature

8.4 Chemical-Gene Co-Occurrences in Literature

8.5 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

10 Biological Test Results

10.1 BioAssay Results

11 Classification

11.1 ChEBI Ontology

11.2 LIPID MAPS Classification

11.3 ChEMBL Target Tree

11.4 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. ChEBI
  2. ChEMBL
    LICENSE
    Access 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.html
  3. EPA DSSTox
  4. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  5. MassBank Europe
  6. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  7. Metabolomics Workbench
  8. Pharos
    LICENSE
    Data 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 Acid
    https://pharos.nih.gov/ligands/2KPQTP9M9CZL
  9. Springer Nature
  10. Wikidata
  11. PubChem
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  13. PATENTSCOPE (WIPO)
CONTENTS