Showing metabocard for Methyl 2-hydroxy benzoate (MMDBc0033418)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:47:45 UTC
Update Date2022-08-31 22:35:56 UTC
Metabolite IDMMDBc0033418
Metabolite Identification
Common NameMethyl 2-hydroxy benzoate
DescriptionMethyl 2-hydroxybenzoate, also known as methyl salicylate, 2-(methoxycarbonyl)phenol or 2-carbomethoxyphenol, belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. Methyl 2-hydroxybenzoate is a mint, peppermint, and wintergreen tasting compound. Methyl 2-hydroxybenzoate is found, on average, in the highest concentration within hyssops and bilberries. Methyl 2-hydroxybenzoate has also been detected, but not quantified, in several different foods, such as chinese cinnamons, tamarinds, tea, mushrooms, and roselles. Minor metabolism may occur in various tissues but hepatic metabolism constitutes the majority of metabolic processes of absorbed methyl salicylate. Methyl 2-hydroxybenzoate is a potentially toxic compound. Present in white wine, tea, porcini mushroom Boletus edulis, Bourbon vanilla, clary sage, red sage and fruits including cherry, apple, raspberry, papaya and plum. For acute joint and muscular pain, Methyl 2-hydroxybenzoate is used as a rubefacient and analgesic in deep heating liniments. This is thought to mask the underlying musculoskeletal pain and discomfort. Severe toxicity can result in acute lung injury, lethargy, coma, seizures, cerebral edema, and death. Counter-irritation is believed to cause a soothing sensation of warmth. Methyl salicylate plays a role as a signaling molecule in plants.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f124195bde8>


  Mrv1652303202019012D          

 11 11  0  0  0  0            999 V2000
    6.7185   -6.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012   -5.3893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0098   -6.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012   -6.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0098   -7.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -6.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012   -7.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -7.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4480   -6.6462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1604   -6.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7150   -5.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
  1  3  1  0  0  0  0
  1  9  1  0  0  0  0
  1 11  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f124195bde8>

HMDB0034172
     RDKit          3D
Methyl 2-hydroxybenzoate
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.5128    0.1652    0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1230    0.4632    0.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524   -0.5306    0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284   -1.6997    0.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535   -0.1334   -0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5519    1.2281   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156    1.6706   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    0.7601   -0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6375   -0.5828   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005   -1.0156   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1236   -2.3775    0.1045 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146    0.8196    1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -0.8730    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0172    0.4171   -0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633    1.9371   -0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486    2.7399   -0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649    1.1648   -0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441   -1.3034   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790   -2.8498    0.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
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3D SDF for #<Metabolite:0x00007f124195bde8>


  Mrv1652303202019012D          

 11 11  0  0  0  0            999 V2000
    6.7185   -6.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012   -5.3893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0098   -6.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012   -6.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0098   -7.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -6.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012   -7.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -7.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4480   -6.6462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1604   -6.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7150   -5.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
  1  3  1  0  0  0  0
  1  9  1  0  0  0  0
  1 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033418

> <DATABASE_NAME>
MIME

> <SMILES>
COC(=O)C1=C(O)C=CC=C1

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

> <INCHI_KEY>
OSWPMRLSEDHDFF-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.982038591572135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-hydroxybenzoate

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.3231574583333336

> <ALOGPS_LOGS>
-1.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.722685015540604

> <JCHEM_PKA_STRONGEST_BASIC>
-4.287418929758233

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
40.0642

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl salicylate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f124195bde8>

HMDB0034172
     RDKit          3D
Methyl 2-hydroxybenzoate
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.5128    0.1652    0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1230    0.4632    0.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524   -0.5306    0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284   -1.6997    0.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535   -0.1334   -0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5519    1.2281   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156    1.6706   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    0.7601   -0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6375   -0.5828   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005   -1.0156   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1236   -2.3775    0.1045 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146    0.8196    1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -0.8730    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0172    0.4171   -0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633    1.9371   -0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486    2.7399   -0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649    1.1648   -0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441   -1.3034   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790   -2.8498    0.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
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PDB for #<Metabolite:0x00007f124195bde8>

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      12.541 -11.619   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.896 -10.060   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.218 -12.399   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.896 -11.619   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.218 -13.957   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.567 -12.399   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.896 -14.737   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.567 -13.957   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.903 -12.406   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      15.233 -11.639   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.535 -10.084   0.000  0.00  0.00           O+0
CONECT    1    3    9   11                                                  
CONECT    2    4                                                            
CONECT    3    4    5    1                                                  
CONECT    4    2    3    6                                                  
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9   10    1                                                       
CONECT   10    9                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007f124195bde8>

COMPND    HMDB0034172
HETATM    1  C1  UNL     1       3.513   0.165   0.276  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.123   0.463   0.133  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.152  -0.531   0.137  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.528  -1.700   0.270  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.254  -0.133  -0.017  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.552   1.228  -0.160  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.816   1.671  -0.306  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.863   0.760  -0.315  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.637  -0.583  -0.180  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.301  -1.016  -0.029  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.124  -2.378   0.104  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.915   0.820   1.089  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.671  -0.873   0.625  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.017   0.417  -0.655  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.263   1.937  -0.153  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.049   2.740  -0.418  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.865   1.165  -0.435  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.444  -1.303  -0.185  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.279  -2.850   0.217  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   10
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   19
END
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SMILES for #<Metabolite:0x00007f124195bde8>

COC(=O)C1=C(O)C=CC=C1
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INCHI for #<Metabolite:0x00007f124195bde8>

InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
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Synonyms
ValueSource
2-(Methoxycarbonyl)phenolChEBI
2-CarbomethoxyphenolChEBI
2-Hydroxybenzoic acid methyl esterChEBI
Betula oilChEBI
Gaultheria oilChEBI
Methyl O-hydroxybenzoateChEBI
Natural wintergreen oilChEBI
Oil OF wintergreenChEBI
Spicewood oilChEBI
Sweet birch oilChEBI
Teaberry oilChEBI
2-Hydroxybenzoate methyl esterGenerator
Methyl O-hydroxybenzoic acidGenerator
Methyl 2-hydroxybenzoic acidGenerator
Benzoic acid, 2-hydroxy-, methyl esterHMDB
FEMA 2745HMDB
Methyl ester 2-hydroxy-benzoic acidHMDB
Methyl salicylate, 8ciHMDB
O-Hydroxybenzoic acid, methyl esterHMDB
MethylsalicylateMeSH, HMDB
RheumabalMeSH, HMDB
HewedolorMeSH, HMDB
LinsalMeSH, HMDB
Metsal linimentMeSH, HMDB
Methyl salicylate sodium saltMeSH, HMDB
Methyl 2-hydroxybenzoateChEBI
Methyl salicylic acidGenerator, HMDB
Methyl ester 2-hydroxy benzoic acidHMDB
Methyl ester of 2-hydroxy benzoic acidHMDB
Methyl salicylateHMDB
o-Hydroxybenzoic acid methyl esterHMDB
Molecular FormulaC8H8O3
Average Mass152.1473
Monoisotopic Mass152.047344122
IUPAC Namemethyl 2-hydroxybenzoate
Traditional Namemethyl salicylate
CAS Registry Number119-36-8
SMILES
COC(=O)C1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
InChI KeyOSWPMRLSEDHDFF-UHFFFAOYSA-N