LIPID MAPS

Structure Database (LMSD)

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Common Name

Isocicutoxin

Systematic Name

(8E,10E,12E,14R)-heptadeca-8,10,12-trien-4,6-diyne-1,14-diol

Synonyms

LM ID

LMFA05000747

Formula

C₁₇H₂₂O₂

Exact Mass

Calculate m/z

258.16198

Sum Composition

FOH 17:7;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Cicuta (#48035)

Magnoliopsida (#3398)

Absolute stereochemistry of cicutoxin and related toxic polyacetylenic alcohols from Cicuta virosa,
Tetrahedron, 1999

DOI: 10.1016/S0040-4020(99)00706-1

String Representations

InChiKey (Click to copy)

FQVNSJQTSOVRKZ-AHBIEKGCSA-N

InChi (Click to copy)

InChI=1S/C17H22O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10,12,15,17-19H,2,11,13-14,16H2,1H3/b6-4-,10-8+,15-12+/t17-/m1/s1

SMILES (Click to copy)

C(CCC#CC#C/C=C\C=C\C=C\[C@H](O)CCC)O

Other Databases

PubChem CID

92034568

Calculated Physicochemical Properties

Heavy Atoms 19

Rings

Aromatic Rings

Rotatable Bonds 7

Van der Waals Molecular Volume 301.76

Topological Polar Surface Area 40.46

Hydrogen Bond Donors 2

Hydrogen Bond Acceptors 2

logP 3.17

Molar Refractivity 81.21

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Created at

12th Nov 2021

Updated at