Structure Database (LMSD)
Common Name
6Z,9Z,12Z,15Z,18Z-heneicosapentaenoic acid
Systematic Name
6Z,9Z,12Z,15Z,18Z-heneicosapentaenoic acid
Synonyms
- C21:5n-3,6,9,12,15
3D model of 6Z,9Z,12Z,15Z,18Z-heneicosapentaenoic 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
Heneicosapentaenoic Acid (HPA) is a 21:5 ω-3 fatty acid present in trace amounts in the green alga B. pennata and in fish oils. Its chemical composition is similar to eicosapentaenoic acid (EPA) except elongated with one carbon on the carboxyl end, placing the first double bond in the Δ6 position.1 HPA can be used to study the significance of the position of the double bonds in ω-3 fatty acids. It incorporates into phospholipids and into triacylglycerol in vivo with the same efficiency as EPA and docosahexaenoic acid and exhibits strong inhibition of arachidonic acid synthesis from linoleic acid.1 HPA is a poor substrate for prostaglandin H synthase (PGHS) (cyclooxygenase) and for 5-lipoxygenase but retains the ability to rapidly inactivate PGHS.1
This information has been provided by Cayman Chemical
References
1. Larsen, L.N., Hovik, K., Bremer, J., et al. Heneicosapentaenoate (21:5n-3): Its incorporation into lipids and its effects on arachidonic acid and eicosanoid synthesis. Lipids 32(7), 707-714 (1997).
Reactions
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References
String Representations
InChiKey (Click to copy)
OQOCQFSPEWCSDO-JLNKQSITSA-N
InChi (Click to copy)
InChI=1S/C21H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(22)23/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-20H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
C(CCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
373.60
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
6.38
Molar Refractivity
100.56
Admin
Created at
-
Updated at
25th Apr 2022