Structure Database (LMSD)

Common Name
iso-12-oxo-PDA
Systematic Name
8-[3-oxo-2-[(Z)-pent-2-enyl]cyclopenten-1-yl]octanoic acid
Synonyms
  • 15(Z)-12-oxo-9(13),15-phytodienoic acid
  • iso-12-OPDA
  • Tetrahydrodicranenone B
LM ID
LMFA02010020
Formula
C18H28O3
Exact Mass
Calculate m/z
292.203845
Sum Composition
FA 18:4;O
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]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Oxo fatty acids [FA0106]
Carbocyclic fatty acids [FA0114]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Physcomitrium patens (#3218)
Bryopsida (#3214)
Lipoxygenase pathway in model bryophytes: 12-oxo-9(13),15-phytodienoic acid is a predominant oxylipin in Physcomitrella patens.,
Phytochemistry, 2020
Pubmed ID: 33059187

String Representations

InChiKey (Click to copy)
RHVWQVSLVMXMBR-CLTKARDFSA-N
InChi (Click to copy)
InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7H,2,4-6,8-14H2,1H3,(H,20,21)/b7-3-
SMILES (Click to copy)
C(CCCCCCC(=O)O)C1CCC(=O)C=1C/C=C\CC

Other Databases

PubChem CID
10424442

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 1
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 323.41
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 4.82
Molar Refractivity 85.27

Admin

Created at
6th May 2022
Updated at
6th May 2022