Showing metabocard for 6-methylsalicylate (MMDBc0055605)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 20:00:06 UTC
Update Date2025-10-07 16:09:13 UTC
Metabolite IDMMDBc0055605
Metabolite Identification
Common Name6-methylsalicylate
Description6-methylsalicylate is a member of the salicylate chemical class, characterized by its methylated phenolic structure. This compound is involved in various biochemical pathways, particularly in the biosynthesis of secondary metabolites. It has been identified as a key component in pheromone blends, specifically in the sex attractant pheromone of the slave-making ant Polyergus samurai, where it is combined with other compounds to elicit electroantennogram responses in both male and female ants (PMID:39305440 , PMID:32318903 ). Additionally, 6-methylsalicylate is synthesized through microbial pathways, notably in Corynebacterium glutamicum, highlighting its potential in biotechnological applications (PMID:31686146 ). The compound also plays a role in the biosynthesis of other natural products, such as cahuitamycin C, where it is produced via a convergent biosynthetic pathway involving a 6-methylsalicylate synthase (PMID:26880271 ). Furthermore, the shikimate pathway is essential for generating precursors like 3-hydroxyanthranilate, which ultimately leads to the production of 6-methylsalicylate in the biosynthesis of nataxazole (PMID:25892546 ). Overall, 6-methylsalicylate serves as a significant metabolite in various biosynthetic and ecological contexts.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9aa4833b78>


  Mrv1652306172222002D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
M  CHG  1   9  -1
M  END
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3D MOL for #<Metabolite:0x00007f9aa4833b78>

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3D SDF for #<Metabolite:0x00007f9aa4833b78>

  Mrv1652306172222002D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
M  CHG  1   9  -1
M  END
> <DATABASE_ID>
MMDBc0055605

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(C(O)=O)C([O-])=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4,9H,1H3,(H,10,11)/p-1

> <INCHI_KEY>
HCJMNOSIAGSZBM-UHFFFAOYSA-M

> <FORMULA>
C8H7O3

> <MOLECULAR_WEIGHT>
151.142

> <EXACT_MASS>
151.040067665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.457464711347203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-carboxy-3-methylbenzen-1-olate

> <JCHEM_LOGP>
2.490684791666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.39030305470003

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.684599412232767

> <JCHEM_PKA_STRONGEST_BASIC>
-6.285792001102007

> <JCHEM_POLAR_SURFACE_AREA>
60.36

> <JCHEM_REFRACTIVITY>
50.8866

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-carboxy-3-methylbenzenolate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9aa4833b78>
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PDB for #<Metabolite:0x00007f9aa4833b78>
HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    1    3    7                                                  
CONECT    6    4    7    9                                                  
CONECT    7    5    6    8                                                  
CONECT    8    7   10   11                                                  
CONECT    9    6                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for #<Metabolite:0x00007f9aa4833b78>
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SMILES for #<Metabolite:0x00007f9aa4833b78>
CC1=C(C(O)=O)C([O-])=CC=C1
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INCHI for #<Metabolite:0x00007f9aa4833b78>
InChI=1S/C8H8O3/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4,9H,1H3,(H,10,11)/p-1
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Synonyms
ValueSource
2,6-CresotateChEBI
2-Hydroxy-6-methylbenzoateChEBI
6-Hydroxy-O-toluateChEBI
6-Methyl 2-hydroxybenzenecarboxylateChEBI
2,6-Cresotic acidGenerator
2-Hydroxy-6-methylbenzoic acidGenerator
6-Hydroxy-O-toluic acidGenerator
6-Methyl 2-hydroxybenzenecarboxylic acidGenerator
6-Methylsalicylic acidGenerator
Molecular FormulaC8H7O3
Average Mass151.142
Monoisotopic Mass151.040067665
IUPAC Name2-carboxy-3-methylbenzen-1-olate
Traditional Name2-carboxy-3-methylbenzenolate
CAS Registry NumberNot Available
SMILES
CC1=C(C(O)=O)C([O-])=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4,9H,1H3,(H,10,11)/p-1
InChI KeyHCJMNOSIAGSZBM-UHFFFAOYSA-M