Structure Database (LMSD)
Common Name
alpha-calendic acid
Systematic Name
8E,10E,12Z-octadecatrienoic acid
Synonyms
- trans-8, trans-10, cis-12-octadecatrienoic acid
- C18:3n-6,8,10
- Calendulicacid
- a-calendic acid
3D model of alpha-calendic 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
8(E),10(E),12(Z)-Octadecatrienoic acid is a conjugated polyunsaturated fatty acid (PUFA) that has been found in C. officinalis seed oil and has anticancer activity.1,2,3 It inhibits the growth of Caco-2 cells when used at concentrations ranging from 10 to 50 µM.2 8(E),10(E),12(Z)-Octadecatrienoic acid (10 µM) induces formation of thiobarbituric acid reactive substances (TBARS) and apoptosis in DLD-1 colorectal adenocarcinoma cells.3 It also inhibits prostaglandin biosynthesis in sheep vesicular gland microsomes (IC50 = 31 µM).4
This information has been provided by Cayman Chemical
References
2. Yasui, Y., Hosokawa, M., Kohno, H., et al. Growth inhibition and apoptosis induction by all-trans-conjugated linolenic acids on human colon cancer cells. Anticancer Res. 26(3A), 1855-1860 (2006).
4. Nugteren, D.H., and Christ-Hazelhof, E. Naturally occurring conjugated octadecatrienoic acids are strong inhibitors of prostaglandin biosynthesis. Prostaglandins 33(3), 403-417 (1987).
Reactions
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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.
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String Representations
InChiKey (Click to copy)
DQGMPXYVZZCNDQ-KBPWROHVSA-N
InChi (Click to copy)
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10+
SMILES (Click to copy)
C(=C/C=C\CCCCC)\C=C\CCCCCCC(=O)O
Other Databases
Wikipedia
HMDB ID
CHEBI ID
LIPIDBANK ID
DFA0183
PubChem CID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
0
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
326.98
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
5.66
Molar Refractivity
86.90
Admin
Created at
-
Updated at
25th Apr 2022