Structure Database (LMSD)

Common Name
5-n-heneicosylresorcinol
Systematic Name
5-heneicosylbenzene-1,3-diol
Synonyms
LM ID
LMPK15030005
Formula
C27H48O2
Exact Mass
Calculate m/z
404.365431
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Phenolic lipids [PK15]
Alkyl resorcinols and derivatives [PK1503]

Biological Context

5-Heneicosylresorcinol is an alkylresorcinol that has been found in wheat, rye, triticale, and barley.1 It reduces hydrogen peroxide-induced DNA damage in HT-29 cells when used at a concentration of 100 µmol/L.2 5-Heneicosylresorcinol (160 µg/ml), when used in combination with 5-nonadecanoylresorcinol, inhibits migration and invasion, reduces the number of LC3 puncta, a marker of autophagy, and decreases survival in HepG2 cells.3

This information has been provided by Cayman Chemical

References

1. Guo, Y.-Z., Yang, X.-M., and Li, Y.-Y. Effect of alkylresorcinols on autophagy, migration, and invasion of HepG2 cells. J. Food Sci. 84(10), 3063-3068 (2019).
2. Parikka, K., Rowland, I.R., Welch, R.W., et al. In vitro antioxidant activity and antigenotoxicity of 5-n-alkylresorcinols. J. Agric. Food Chem. 54(5), 1646-1650 (2006).
3. Ross, A.B., Shepherd, M.J., Schüpphaus, M., et al. Alkylresorcinols in cereals and cereal products. J. Agric. Food Chem. 51(14), 4111-4118 (2003).

String Representations

InChiKey (Click to copy)
BLHLKJLSYHEOGY-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C27H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-22-26(28)24-27(29)23-25/h22-24,28-29H,2-21H2,1H3
SMILES (Click to copy)
C1(O)C=C(CCCCCCCCCCCCCCCCCCCCC)C=C(O)C=1

Other Databases

HMDB ID
HMDB0031035
CHEBI ID
166655
PubChem CID
155461
Cayman ID
30031

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 1
Aromatic Rings 1
Rotatable Bonds 20
Van der Waals Molecular Volume 462.06
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 9.07
Molar Refractivity 126.87

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Updated at
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