Structure Database (LMSD)

Common Name
Falcarinol
Systematic Name
1,9Z-heptadecadien-4,6-diyn-3R-ol
Synonyms
  • Panaxynol
  • (3R,9Z)-heptadeca-1,9-dien-4,6-diyn-3-ol
  • 1,9-Heptadecadiene-4,6-diyn-3-ol
LM ID
LMFA05000689
Formula
C17H24O
Exact Mass
Calculate m/z
244.182715
Sum Composition
FOH 17:6
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty alcohols [FA05]

Biological Context

Falcarinol is a C17-polyacetylene produced by the Apiaceae family that has antimicrobial properties due to its inhibition of fatty acid biosynthesis.1,2 Falcarinol binds to the human recombinant cannabinoid (CB) receptors, CB1 and CB2, (Kis = 594 and 2,100 nM, respectively) in an [3H]anandamide displacement assay in HEK293 cells.3 It differentially modulates synaptic and extrasynaptic GABAA receptors in a recombinant HEK293 system.4 In vitro assays of ATPase activity demonstrate that falcarinol inhibits breast cancer resistance protein ATP-binding cassette sub-family G member 2 (ABCG2; IC50 = 79.3 μM), a drug efflux transporter and mediator of drug resistance.5 Falcarinol (6.88 μg/g feed) also inhibits aberrant crypt foci by 26.6% in azoxymethane-induced rats.6

This information has been provided by Cayman Chemical

References

1. Czyzewska, M.M., Chrobok, L., Kania, A., et al. Dietary acetylenic oxylipin falcarinol differentially modulates GABAA receptors. J. Nat. Prod. 77(12), 2671-2677 (2014).
2. Dawid, C., Dunemann, F., Schwab, W., et al. Bioactive C₁₇-polyacetylenes in carrots (Daucus carota L.): Current knowledge and future perspectives. J. Agric. Food Chem. 63(42), 9211-9222 (2015).
3. Kobaek-Larsen, M., El-Houri, R.B., Christensen, L.P., et al. Dietary polyacetylenes, falcarinol and falcarindiol, isolated from carrots prevents the formation of neoplastic lesions in the colon of azoxymethane-induced rats. Food Funct. 8(3), 964-974 (2017).
4. Leonti, M., Casu, L., Raduner, S., et al. Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin. Biochem. Pharmacol. 79(12), 1815-1826 (2010).
5. Li, H., Cowie, A., Johnson, J.A., et al. Determining the mode of action of antimycobacterial C17 diyne natural products using expression profiling: Evidence for fatty acid biosynthesis inhibition. BMC Genomics 17(1), 621 (2016).
6. Tan, K.W., Killeen, D.P., Li, Y., et al. Dietary polyacetylenes of the falcarinol type are inhibitors of breast cancer resistance protein (BCRP/ABCG2). Eur. J. Pharmacol. 723, 346-352 (2014).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Daucus carota (#4039)
Magnoliopsida (#3398)
Bioactive C₁₇-Polyacetylenes in Carrots (Daucus carota L.): Current Knowledge and Future Perspectives.,
J Agric Food Chem, 2015
Pubmed ID: 26451696

String Representations

InChiKey (Click to copy)
UGJAEDFOKNAMQD-QXPKXGMISA-N
InChi (Click to copy)
InChI=1S/C17H24O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h4,10-11,17-18H,2-3,5-9,12H2,1H3/b11-10-/t17-/m1/s1
SMILES (Click to copy)
O[C@H](C=C)C#CC#CC/C=C\CCCCCCC

Other Databases

Wikipedia
Falcarinol
KEGG ID
C08450
CHEBI ID
66722
PubChem CID
5281149
Cayman ID
22407

Calculated Physicochemical Properties

Heavy Atoms 18
Rings 0
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 295.61
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 4.13
Molar Refractivity 79.40

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Created at
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Updated at
4th Apr 2022