Structure Database (LMSD)
Common Name
Myristoleic acid
Systematic Name
9Z-tetradecenoic acid
Synonyms
- cis-9-tetradecenoic acid
- C14:1n-5
3D model of Myristoleic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Myristoleic acid is a monounsaturated fatty acid found in the fruit extract of S. repens and in dairy extracts.1,2 It induces apoptosis and necrosis in human prostate cancer LNCaP cells at a rate of 8.8% and 8.1%, respectively.1 Myristoleic acid inhibits C. albicans germination in vitro with a minimal inhibitory concentration (MIC) of 9 µM.3 Furthermore, myristoleic acid inhibits osteogenesis in vitro via interference with cytoskeletal rearrangement and prevents RANKL-induced bone loss and osteoclast formation in mice.4
This information has been provided by Cayman Chemical
References
1. Clément, M., Tremblay, J., Lange, M., et al. Whey-derived free fatty acids suppress the germination of Candida albicans in vitro. FEMS Yeast Res. 7(2), 276-285 (2007).
2. Iguchi, K., Okumura, N., Usui, S., et al. Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells. Prostate 47(1), 59-65 (2001).
Reactions
Filter by species:
ⓘ
Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
String Representations
InChiKey (Click to copy)
YWWVWXASSLXJHU-WAYWQWQTSA-N
InChi (Click to copy)
InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-
SMILES (Click to copy)
C(/C=C\CCCC)CCCCCCC(=O)O
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
DFA0090
PubChem CID
PlantFA ID
SwissLipids ID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
16
Rings
0
Aromatic Rings
0
Rotatable Bonds
11
Van der Waals Molecular Volume
263.06
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
4.55
Molar Refractivity
68.62
Admin
Created at
-
Updated at
25th Apr 2022