Structure Database (LMSD)

Common Name
Falcarindiol
Systematic Name
(3R,8S,9Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol
Synonyms
  • (3R,8S)-Falcarindiol
  • (3R,8S,9Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol
  • (3S,8S)-Falcarindiol
  • AC1NQY3Z
LM ID
LMFA05000658
Formula
C17H24O2
Exact Mass
Calculate m/z
260.17763
Sum Composition
FOH 17:6;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

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

Biological Context

(3R,8S)-Falcarindiol is a polyacetylene that has been found in N. incisum and has diverse biological activities.1,2,3 It is active against M. tuberculosis strain H37Ra (MIC = 6.25 μg/ml).1 (3R,8S)-Falcarindiol is cytotoxic to MCF-7, H1299, and HepG2 cells (IC50s = 29.4, 22.1, and 23.6 μM, respectively).2 It has algicidal activity against H. circularisquama when used at concentrations of 2 and 4 μM.3

This information has been provided by Cayman Chemical

References

1. Tamura, S., Ohno, T., Hattori, Y., et al. Establishment of absolute stereostructure of falcarindiol, algicidal principle against Heterocapsa circularisquama from Notopterygii Rhizoma. Tetrahedron Lett. 51(11), 1523-1525 (2010).
2. Zheng, X., Zheng, X., Zhang, C., et al. Cytotoxic polyacetylenes isolated from the roots and rhizomes of Notopterygium incisum. Chinese Chem. Lett. 30(2), 428-430 (2019).
3. O'Neill, T., Johnson, J.A., Webster, D., et al. The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins. J. Ethnopharmacol. 147(1), 232-237 (2013).

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)
QWCNQXNAFCBLLV-YWALDVPYSA-N
InChi (Click to copy)
InChI=1S/C17H24O2/c1-3-5-6-7-8-9-10-14-17(19)15-12-11-13-16(18)4-2/h4,10,14,16-19H,2-3,5-9H2,1H3/b14-10-/t16-,17+/m1/s1
SMILES (Click to copy)
O[C@H](C#CC#C[C@@H](C=C)O)/C=C\CCCCCCC

Other Databases

KEGG ID
C08449
PubChem CID
5281148
Cayman ID
30919

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 0
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 304.40
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 3.39
Molar Refractivity 81.30

Admin

Created at
-
Updated at
4th Apr 2022