Structure Database (LMSD)

Common Name
Garcinoic acid
Systematic Name
(6-hydroxy-2R,8-dimethyl-3,4-dihydrochromen-2-yl)-2,6,10-trimethyltrideca-2E,6E,10E-trienoic acid
Synonyms
  • trans-delta-tocotrienoloic acid
LM ID
LMPR02020069
Formula
C27H38O4
Exact Mass
Calculate m/z
426.27701
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Prenol Lipids [PR]
Quinones and hydroquinones [PR02]
Vitamin E [PR0202]

Biological Context

Garcinoic acid is a derivative of vitamin E originally isolated from C. grandiflora.1 It inhibits IL-1β-induced microsomal prostaglandin E2 synthase-1 (mPGES-1) activity in A549 cells when used at concentrations of 1 and 10 µM.2 It has higher antioxidant activity relative to (±)-α-tocopherol in a cell-free assay when used at a concentration of 0.15 mM.3

This information has been provided by Cayman Chemical

References

1. Monache, F.D., Marta, M., Mac-Quhae, M.M., et al. Two new tocotrienoloic acids from the fruits of Clusia grandiflora Splith. Gazz. Chim. Ital. 114(3-4), 135-137 (1984).
2. Alsabil, K., Suor-Cherer, S., Koeberle, A., et al. Semisynthetic and natural garcinoic acid isoforms as new mPGES-1 inhibitors. Planta Med. 82(11-12), 1110-1116 (2016).
3. Terashima, K., Takaya, Y., and Niwa, M. Powerful antioxidative agents based on garcinoic acid from Garcinia kola. Bioorg. Med. Chem. 10(5), 1619-1625 (2002).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Garcinia kola (#469930)
Magnoliopsida (#3398)
Configuration of the vitamin E analogue garcinoic acid extracted from Garcinia Kola seeds.,
Chirality, 2009
Pubmed ID: 18655162

String Representations

InChiKey (Click to copy)
QOFWRHWADNWKSU-LRXIOGKNSA-N
InChi (Click to copy)
InChI=1S/C27H38O4/c1-19(11-7-13-21(3)26(29)30)9-6-10-20(2)12-8-15-27(5)16-14-23-18-24(28)17-22(4)25(23)31-27/h9,12-13,17-18,28H,6-8,10-11,14-16H2,1-5H3,(H,29,30)/b19-9+,20-12+,21-13+/t27-/m1/s1
SMILES (Click to copy)
C1C(=CC(=C2O[C@@](C)(CCC=12)CC/C=C(\C)/CC/C=C(\C)/CC/C=C(/C(O)=O)\C)C)O

Other Databases

CHEBI ID
190931
PubChem CID
10455173
Cayman ID
28122
GuidePharm ID
10734

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 2
Aromatic Rings 1
Rotatable Bonds 10
Van der Waals Molecular Volume 456.72
Topological Polar Surface Area 68.83
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 7.33
Molar Refractivity 127.32

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Created at
10th Jul 2020
Updated at
10th Jul 2020