Structure Database (LMSD)

Common Name
6-((Z)-pentadec-8-en-1-yl)salicylic acid
Systematic Name
(Z)-2-(pentadec-8-en-1-yl)-6-hydroxybenzoic acid
Synonyms
  • Ginkgolic acid
LM ID
LMPK15040003
Formula
C22H34O3
Exact Mass
Calculate m/z
346.250796
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Phenolic lipids [PK15]
Anacardic acids and derivatives [PK1504]

Biological Context

Ginkgolic acid C15:1 is a 2-hydroxy-6-alkylbenzoic acid in which the alkyl chain contains 15 carbons and is unsaturated at the 8 position.1 It inhibits SUMOylation in vitro (IC50 = 3 µM) and in cells without affecting protein ubiquitination.2,3 Ginkgolic acid C15:1 directly binds the SUMO-activating enzyme E1, blocking the formation of the E1-SUMO intermediate.2 Ginkgolic acid C15:1 also suppresses the development of pancreatic cancer xenografts in mice.4

This information has been provided by Cayman Chemical

References

1. Fukuda, I., Ito, A., Hirai, G., et al. Ginkgolic acid inhibits protein SUMOylation by blocking formation of the E1-SUMO intermediate. Chem. Biol. 16, 133-140 (2009).
2. He, X.g., Bernart, M.W., Nolan, G.S., et al. High-performance liquid chromatography-electrospray ionization-mass spectrometry study of ginkgolic acid in the leaves and fruits of the ginkgo tree (Ginkgo biloba). J. Chromatogr. Sci. 38, 169-173 (2000).
3. Luo, H.B., Xia, Y.Y., Shu, X.J., et al. SUMOylation at K340 inhibits tau degradation through deregulating its phosphorylation and ubiquitination. Proc. Natl. Acad. Sci. USA 111(46), 16586-16591 (2014).
4. Ma, J., Duan, W., Han, S., et al. Ginkgolic acid suppresses the development of pancreatic cancer by inhibiting pathways driving lipogenesis. Oncotarget 6(25), 20993-21003 (2015).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Anacardium occidentale (#171929)
Magnoliopsida (#3398)
Antibacterial agents from the cashew Anacardium occidentale (Anacardiaceae) nut shell oil,
J. Agric. Food Chem., 1991

String Representations

InChiKey (Click to copy)
YXHVCZZLWZYHSA-FPLPWBNLSA-N
InChi (Click to copy)
InChI=1S/C22H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h7-8,15,17-18,23H,2-6,9-14,16H2,1H3,(H,24,25)/b8-7-
SMILES (Click to copy)
C1C=C(CCCCCCC/C=C\CCCCCC)C(C(O)=O)=C(O)C=1

Other Databases

KEGG ID
C10794
CHEBI ID
5354
PubChem CID
5281858
Cayman ID
18422

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 1
Rotatable Bonds 14
Van der Waals Molecular Volume 379.07
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.50
Molar Refractivity 104.37

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Created at
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Updated at
2nd Feb 2022