Structure Database (LMSD)

Common Name
12-oxo-PDA-Phe
Systematic Name
N-(1S,2S)-3-oxo-2-(2'Z-pentenyl)cyclopent-4-eneoctanyl phenylalanine
Synonyms
  • (cis)-(+)-OPDA-Phe
  • N-12-oxo-phytodienyl phenylalanine
LM ID
LMFA02010027
Formula
C27H37NO4
Exact Mass
Calculate m/z
439.272259
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Octadecanoids [FA02]
12-oxophytodienoic acid metabolites [FA0201]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Arabidopsis thaliana (#3702)
Magnoliopsida (#3398)
Amide conjugates of the jasmonate precursor cis-OPDA regulate its homeostasis during plant stress responses.,
Plant Physiol, 2024
Pubmed ID: 39607728

String Representations

InChiKey (Click to copy)
SVCBGFMYXWRPLR-QVOALPAMSA-N
InChi (Click to copy)
InChI=1S/C27H37NO4/c1-2-3-8-16-23-22(18-19-25(23)29)15-11-5-4-6-12-17-26(30)28-24(27(31)32)20-21-13-9-7-10-14-21/h3,7-10,13-14,18-19,22-24H,2,4-6,11-12,15-17,20H2,1H3,(H,28,30)(H,31,32)/b8-3-/t22-,23-,24-/m0/s1
SMILES (Click to copy)
N(C(CCCCCCC[C@@H]1[C@@H](C(C=C1)=O)C/C=C\CC)=O)[C@@H](CC1=CC=CC=C1)C(O)=O

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 2
Aromatic Rings 1
Rotatable Bonds 15
Van der Waals Molecular Volume 465.08
Topological Polar Surface Area 83.47
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 5.54
Molar Refractivity 127.72

Admin

Created at
10th Dec 2024
Updated at
10th Dec 2024