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Showing NP-Card for 6-Methylsalicylic acid (NP0050352)

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Record Information
Version2.0
Created at2022-04-27 20:55:19 UTC
Updated at2022-04-27 20:55:19 UTC
NP-MRD IDNP0050352
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-Methylsalicylic acid
Description6-Methylsalicylic acid, also known as methylsalicylate or 2,6-cresotic acid, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. 6-Methylsalicylic acid is found in Aspergillus flavipes, Aspergillus fumigatus, Aspergillus terreus IMI16043 , Epicoccum sorghinum, Eriodictyon angustifolium, Garcinia mangostana, Lasiodiplodia theobromae, Mutisia spinosa, Neolentinus cyathiformis, Penicillium griseofulvum, Penicillium solitum, Penicillium spp., Penicillium vulpinum, Phyllosticta spp., Streptomyces coelicolor, Streptomyces viridochromogenes Tu57 and Tetramorium impurum. 6-Methylsalicylic acid was first documented in 1966 (PMID: 5973021). 6-Methylsalicylic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 1225916) (PMID: 16345795) (PMID: 20534347) (PMID: 24699147).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050352 (6-Methylsalicylic acid)


  Mrv1652310051712512D          

 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  0  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  END
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3D MOL for NP0050352 (6-Methylsalicylic acid)

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3D SDF for NP0050352 (6-Methylsalicylic acid)

  Mrv1652310051712512D          

 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  0  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  END
> <DATABASE_ID>
NP0050352

> <DATABASE_NAME>
NP-MRD

> <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)

> <INCHI_KEY>
HCJMNOSIAGSZBM-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.149

> <EXACT_MASS>
152.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.807473061867052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-6-methylbenzoic acid

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.490684791666667

> <ALOGPS_LOGS>
-1.71

> <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>
57.53

> <JCHEM_REFRACTIVITY>
40.3363

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylsalicylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050352 (6-Methylsalicylic acid)
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PDB for NP0050352 (6-Methylsalicylic acid)
HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         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+0
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 NP0050352 (6-Methylsalicylic acid)
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SMILES for NP0050352 (6-Methylsalicylic acid)
CC1=C(C(O)=O)C(O)=CC=C1
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INCHI for NP0050352 (6-Methylsalicylic acid)
InChI=1S/C8H8O3/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4,9H,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
2,6-Cresotic acidChEBI
2-Hydroxy-6-methylbenzoic acidChEBI
2-Hydroxymethylbenzoic acidChEBI
6-Hydroxy-O-toluic acidChEBI
6-Methyl-2-hydroxybenzenecarboxylateChEBI
Methylsalicylic acidChEBI
2,6-CresotateGenerator
2-Hydroxy-6-methylbenzoateGenerator
2-HydroxymethylbenzoateGenerator
6-Hydroxy-O-toluateGenerator
6-Methyl-2-hydroxybenzenecarboxylic acidGenerator
MethylsalicylateGenerator
6-MethylsalicylateGenerator
6-Methylsalicylic acidKEGG
Chemical FormulaC8H8O3
Average Mass152.1490 Da
Monoisotopic Mass152.04734 Da
IUPAC Name2-hydroxy-6-methylbenzoic acid
Traditional Namemethylsalicylic acid
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)
InChI KeyHCJMNOSIAGSZBM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus flavipesLOTUS Database
Aspergillus fumigatusLOTUS Database
Aspergillus terreus IMI16043Fungi
Epicoccum sorghinumLOTUS Database
Eriodictyon angustifoliumPlant
Garcinia mangostanaLOTUS Database
Lasiodiplodia theobromaeLOTUS Database
Mutisia spinosaLOTUS Database
Neolentinus cyathiformisLOTUS Database
Penicillium griseofulvumLOTUS Database
Penicillium solitumLOTUS Database
Penicillium spp.Fungi
Penicillium vulpinumLOTUS Database
Phyllosticta spp.Fungi
Streptomyces coelicolorBacteria
Streptomyces viridochromogenes Tu57Bacteria
Tetramorium impurumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentSalicylic acids  
Alternative Parents
Substituents
  • Salicylic acid
    • 

  • Benzoic acid
    • 

  • Benzoyl
    • 

  • M-cresol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Toluene
    • 

  • Phenol
    • 

  • Vinylogous acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.45ALOGPS
logP2.49ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.68ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.34 m³·mol⁻¹ChemAxon
Polarizability14.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0150437  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002658  
Chemspider IDNot Available
KEGG Compound IDC02657  
BioCyc IDCPD-637  
BiGG IDNot Available
Wikipedia LinkMethylsalicylic acid  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17637  
Good Scents IDNot Available
References
General References
  1. Ohno H, Ohno T, Awaya J, Omura S: Inhibition of 6-methylsalicyclic acid synthesis by the antibiotic cerulenin. J Biochem. 1975 Dec;78(6):1149-52. doi: 10.1093/oxfordjournals.jbchem.a131010. [PubMed:1225916  ] 
  2. Peace JN, Bartman CD, Doerfler DL, Campbell IM: 6-Methylsalicylic Acid Production in Solid Cultures of Penicillium patulum Occurs Only When an Aerial Mycelium Is Present. Appl Environ Microbiol. 1981 Jun;41(6):1407-12. doi: 10.1128/aem.41.6.1407-1412.1981. [PubMed:16345795  ] 
  3. Ding W, Lei C, He Q, Zhang Q, Bi Y, Liu W: Insights into bacterial 6-methylsalicylic acid synthase and its engineering to orsellinic acid synthase for spirotetronate generation. Chem Biol. 2010 May 28;17(5):495-503. doi: 10.1016/j.chembiol.2010.04.009. [PubMed:20534347  ] 
  4. He F, Wang M, Gao M, Zhao M, Bai Y, Zhao C: Chemical composition and biological activities of Gerbera anandria. Molecules. 2014 Apr 2;19(4):4046-57. doi: 10.3390/molecules19044046. [PubMed:24699147  ] 
  5. Bu'Lock JD, Hulme MA, Shepherd D: Inhibition and possible feedback by 6-methylsalicylic acid. Nature. 1966 Sep 3;211(5053):1090-1. doi: 10.1038/2111090a0. [PubMed:5973021  ]