An official website of the United States government

N-oleoyl phenylalanine

PubChem CID
52922059
Structure
N-oleoyl phenylalanine_small.png
Molecular Formula
Synonyms
  • N-oleoyl phenylalanine
  • N-oleoyl-L-phenylalanine
  • 136560-78-6
  • oleoyl-L-Phe-OH
  • N-(9Z-octadecenoyl)-phenylalanine
Molecular Weight
429.6 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-phenylalanine is an N-acyl-L-phenylalanine resulting from the formal condensation of the carboxy group of oleic acid with the amino group of L-phenylalanine. It is a N-acyl-L-phenylalanine and a fatty amide. It is functionally related to an oleic acid. It is a conjugate acid of a N-oleoyl-L-phenylalaninate.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-oleoyl phenylalanine.png

1.2 3D Status

Conformer generation is disallowed since too flexible

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
oleoyl-Phe-OH
Sequence
F
HELM
PEPTIDE1{[CCCCCCCC/C=C\CCCCCCCC(=O)N[C@@H](Cc1ccccc1)C(=O)O]}$$$$
IUPAC
N-oleoyl-L-phenylalanine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2S)-2-[[(Z)-octadec-9-enoyl]amino]-3-phenylpropanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

3.1.2 InChI

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
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

3.1.3 InChIKey

UWKNPULCJWBBDD-JRUKXMRZSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

3.1.4 SMILES

CCCCCCCC/C=C\CCCCCCCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C27H43NO3
Computed by PubChem 2.1 (PubChem release 2021.05.07)

3.3 Other Identifiers

3.3.1 CAS

136560-78-6

3.3.2 ChEBI ID

3.3.3 ChEMBL ID

3.3.4 DSSTox Substance ID

3.3.5 HMDB ID

3.3.6 Lipid Maps ID (LM_ID)

3.3.7 Metabolomics Workbench 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
429.6 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
8.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
19
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
429.32429423 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
429.32429423 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 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
31
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
483
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
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 2021.05.07)

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 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

164.0721 100

91.0559 61.82

147.0456 19.01

280.2646 17.82

292.2637 4.12

Thumbnail
Thumbnail
2 of 6
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

428.3169 100

164.0717 2.40

Thumbnail
Thumbnail

5.1.2 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
7.193 min
Precursor m/z
430.3316
Precursor Adduct
[M+H]+
Top 5 Peaks

430.332 999

166.0857 97

384.3267 8

412.3221 7

120.0812 5

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
7.193 min
Precursor m/z
430.3316
Precursor Adduct
[M+H]+
Top 5 Peaks

166.0855 999

430.3314 139

120.0806 134

167.0887 91

384.3256 46

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. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  5. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  6. MassBank Europe
  7. 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
  8. Metabolomics Workbench
  9. Springer Nature
  10. Wikidata
  11. PubChem
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  13. PATENTSCOPE (WIPO)
CONTENTS