Structure Database (LMSD)
Common Name
Thapsic acid
Systematic Name
Hexadecanedioic acid
Synonyms
- Thaspic acid
LM ID
LMFA01170022
Formula
Exact Mass
Calculate m/z
286.21441
Sum Composition
Status
Curated
3D model of Thapsic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Hexadecanedioic acid is a dicarboxylic fatty acid that has been found in the suberin component of silver birch (B. pendula) outer bark and soil.1,2 It stimulates mitochondrial respiration and decreases the production of reactive oxygen species (ROS) induced by rotenone in isolated rat liver mitochondria when used at concentrations of 100 and 40 µM, respectively.3
This information has been provided by Cayman Chemical
References
1. Karnaouri, A., Lange, H., Crestini, C., et al. Chemoenzymatic fractionation and characterization of pretreated birch outer bark. ACS Sustainable Chem. Eng. 4(10), 5289-5302 (2016).
2. Hamer, U., Rumpel, C., and Dignac, M.-F. Cutin and suberin biomarkers as tracers for the turnover of shoot and root derived organic matter along a chronosequence of Ecuadorian pasture soils. Eur. J. Soil Sci. 63(6), 808-819 (2012).
3. Sememova, A.A., V.N., S., Pavlova, S.I., et al. ω-Hydroxypalmitic and α,ω-hexadecanedioic acids as activators of free respiration and inhibitors of H2O2 generation in liver mitochondria. Biochem. Moscow Suppl. Ser. A 14(1), 24-33 (2020).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Subcellular localization of hexadecanedioic acid activation in human liver.,
J Lipid Res, 1974
J Lipid Res, 1974
Pubmed ID:
4372285
Thapsia garganica
(#79022)
Magnoliopsida
(#3398)
“Thapsic acid.” Merriam-Webster.com Dictionary, Merriam-Webster, https://www.merriam-webster.com/dictionary/thapsic%20acid. Accessed 8 Feb. 2021.
String Representations
InChiKey (Click to copy)
QQHJDPROMQRDLA-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)
SMILES (Click to copy)
C(CCCCCCCCCCCCCCC(=O)O)(=O)O
Other Databases
LIPIDAT ID
1814
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
PlantFA ID
SwissLipids ID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
0
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
315.24
Topological Polar Surface Area
74.60
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
4.62
Molar Refractivity
79.91
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