Structure Database (LMSD)

Common Name
Geranylgeranoic acid
Systematic Name
3,7,11,15-tetramethyl-(2E,6E,10E,14E)-hexadecatetraenoic acid
Synonyms
  • Geranylgeranic acid
LM ID
LMPR0104010039
Formula
C20H32O2
Exact Mass
Calculate m/z
304.24023
Sum Composition
FA 20:4
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C20 isoprenoids (diterpenes) [PR0104]
Acyclic diterpenoids [PR010401]

Biological Context

Geranylgeranoic acid (GGA) is an isoprenoid that has been found in S. chinensis and has anticancer activity.1 It induces apoptosis in Huh7 and PLC/PRF/5 human hepatoma cells and MLE-10 transformed mouse hepatocytes, but not primary mouse hepatocytes, when used at concentrations ranging from 1 to 20 µM. GGA (10 µM) induces apoptosis in Huh7 cells via loss of the mitochondrial membrane potential and activation of interleukin-1β-converting enzyme (ICE) and cysteine protease precursor 32 (CPP32).2 It also inhibits lysine-specific demethylase 1 (LSD1; IC50 = 46.97 µM).3

This information has been provided by Cayman Chemical

References

1. Shidoji, Y., and Ogawa, H. Natural occurrence of cancer-preventive geranylgeranoic acid in medicinal herbs. J. Lipid Res. 45(6), 1092-1103 (2004).
2. Shidoji, Y., Nakamura, N., Moriwaki, H., et al. Rapid loss in the mitochondrial membrane potential during geranylgeranoic acid-induced apoptosis. Biochem. Biophys. Res. Commun. 230(1), 58-63 (1997).
3. Sakane, C., Okitsu, T., Wada, A., et al. Inhibition of lysine-specific demethylase 1 by the acyclic diterpenoid geranylgeranoic acid and its derivatives. Biochem. Biophys. Res. Commun. 444(1), 24-29 (2014).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Schisandra chinensis (#50507)
Magnoliopsida (#3398)
Natural occurrence of cancer-preventive geranylgeranoic acid in medicinal herbs.,
J Lipid Res, 2004
Pubmed ID: 15060084
Homo sapiens (#9606)
Mammalia (#40674)
Unequivocal evidence for endogenous geranylgeranoic acid biosynthesized from mevalonate in mammalian cells.,
J Lipid Res, 2019
Pubmed ID: 30622150

String Representations

InChiKey (Click to copy)
SZNLKILVMCHHSD-OZFNKYQOSA-N
InChi (Click to copy)
InChI=1S/C20H32O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h9,11,13,15H,6-8,10,12,14H2,1-5H3,(H,21,22)/b17-11+,18-13+,19-15+
SMILES (Click to copy)
C/C(/C)=C\CC/C(/C)=C/CC/C(/C)=C/CC/C(/C)=C/C(O)=O

Other Databases

CHEBI ID
84971
PubChem CID
5275521
Cayman ID
9003474

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 0
Aromatic Rings 0
Rotatable Bonds 10
Van der Waals Molecular Volume 358.94
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 6.22
Molar Refractivity 96.04

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Created at
2nd May 2020
Updated at
3rd May 2020