Structure Database (LMSD)

Common Name
Lecanoric acid
Systematic Name
4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoic acid
Synonyms
  • Orsellinate depside
LM ID
LMPK13080001
Formula
C16H14O7
Exact Mass
Calculate m/z
318.073955
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Aromatic polyketides [PK13]
Depsides and depsidones [PK1308]

Biological Context

Lecanoric acid is a naturally occurring depside polyphenol isolated from a variety of lichens.1 It is a potent antioxidant, surpassing ascorbic acid in a 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) free radical scavenging assay (IC50s = 424.51 and 6.42 μg/ml for lecanoric and ascorbic acid, respectively).2 Lecanoric acid has antibacterial and antifungal activities with minimum inhibitory concentrations ranging from 0.5 to 1 mg/ml for a panel of fifteen microorganisms. In a cell viability assay, lecanoric acid exhibits antiproliferative activity against HeLa cells (IC50 = 123.97 μg/ml). Lecanoric acid also exhibits antidiabetic and hypolipidemic properties.1,3

This information has been provided by Cayman Chemical

References

1. Thadhani, V.M., and Karunaratne, V. Potential of lichen compounds as antidiabetic agents with antioxidative properties: A review. Oxid. Med. Cell. Longev. 2017, (2017).
2. Ristić, S., Ranković, B., Kosanić, M., et al. Phytochemical study and antioxidant, antimicrobial and anticancer activities of Melanelia subaurifera and Melanelia fuliginosa lichens. J. Food. Sci. Technol. 53(6), 2804-2816 (2016).
3. Wei, A.-H., Zhou, D.-N., Ruan, J.-L., et al. Characterisation of phenols and antioxidant and hypolipidaemic activities of Lethariella cladonioides. J. Sci. Food Agric. 92(2), 373-379 (2012).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Umbilicaria antarctica (#87272)
Lecanoromycetes (#147547)
Lecanoric acid, a secondary lichen substance with antioxidant properties from Umbilicaria antarctica in maritime Antarctica (King George Island),
Polar Biol, 2009

String Representations

InChiKey (Click to copy)
HEMSJKZDHNSSEW-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H14O7/c1-7-3-9(17)5-11(18)14(7)16(22)23-10-4-8(2)13(15(20)21)12(19)6-10/h3-6,17-19H,1-2H3,(H,20,21)
SMILES (Click to copy)
C1(C(O)=CC(O)=CC=1C)C(=O)OC1C=C(C(C(=O)O)=C(C)C=1)O

Other Databases

KEGG ID
C02868
CHEBI ID
15871
PubChem CID
99613
Cayman ID
22710

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 2
Aromatic Rings 2
Rotatable Bonds 4
Van der Waals Molecular Volume 279.25
Topological Polar Surface Area 124.29
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 7
logP 2.34
Molar Refractivity 79.27

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Created at
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Updated at
4th Feb 2022