Structure Database (LMSD)

Common Name
6-Methylsalicylic acid
Systematic Name
Synonyms
LM ID
LMPK13010002
Formula
C8H8O3
Exact Mass
Calculate m/z
152.047345
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Aromatic polyketides [PK13]
Monocyclic aromatic polyketides [PK1301]

Biological Context

2-hydroxy-6-Methylbenzoic acid is a constituent of G. anandria, a well-known traditional Chinese medicinal herb, and also produced in various fungi, including P. patulum, where it is a precursor to the toxin patulin .1,2 This polyketide is a key structural moiety for many different antibiotic and anticancer agents, including chlorothricin , maduropeptin, neocarzinostatin, and terreic acid.2,3

This information has been provided by Cayman Chemical

References

1. Parascandolo, J.S., Havermann, J., Potter, H.K., et al. Insights into 6-methylsalicylic acid bio-assembly by using chemical probes. Angew. Chem. Int. Ed. Engl. 55(10), 3463-3467 (2016).
2. He, F., Wang, M., Gao, M., et al. Chemical composition and biological activities of Gerbera anandria. Molecules 19(4), 4046-4057 (2014).
3. Guo, C.J., Sun, W.W., Bruno, K.S., et al. Molecular genetic characterization of terreic acid pathway in Aspergillus terreus. Org. Lett. 16(20), 5250-5253 (2014).

String Representations

InChiKey (Click to copy)
HCJMNOSIAGSZBM-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C8H8O3/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4,9H,1H3,(H,10,11)
SMILES (Click to copy)
C1(C(=O)O)C(O)=CC=CC=1C

Other Databases

KEGG ID
C02657
CHEBI ID
17637
PubChem CID
11279
Cayman ID
19199

Calculated Physicochemical Properties

Heavy Atoms 11
Rings 1
Aromatic Rings 1
Rotatable Bonds 1
Van der Waals Molecular Volume 139.51
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 1.40
Molar Refractivity 39.80

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Updated at
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