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Showing metabocard for 5-Methoxysalicylic acid (HMDB0001868)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-23 11:14:42 UTC
Update Date2023-02-21 17:15:53 UTC
HMDB IDHMDB0001868
Secondary Accession Numbers
  • HMDB01868
Metabolite Identification
Common Name5-Methoxysalicylic acid
Description5-methoxysalicylic acid is a methoxysalicylic acid that is salicylic acid which is carrying a methoxy group at position 5. It has a role as a bacterial metabolite and a human urinary metabolite. 5-Methoxysalicylic acid is also known as 2-hydroxy-5-methoxybenzoate or 5-methoxy-2-hydroxybenzoate and belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Outside of the human body, 5-Methoxysalicylic acid has been detected, but not quantified in herbs and spices and tea.
Structure
Data?1676999753
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001868 (5-Methoxysalicylic acid)

  Mrv1652305271900002D          

 12 12  0  0  0  0            999 V2000
   18.9347   -6.3195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -3.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0769   -4.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -3.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9347   -7.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -3.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -5.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -4.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -5.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -6.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  8  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  2  0  0  0  0
  6  9  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 10  2  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
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3D MOL for HMDB0001868 (5-Methoxysalicylic acid)

HMDB0001868
     RDKit          3D
5-Methoxysalicylic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.2037   -0.8397    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273    0.4508    0.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    0.5850    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635    1.8339    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079    1.9666    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5004    0.8326    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728    0.9559    0.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -0.4493    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131   -1.6237    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401   -2.7826    0.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -1.5025    0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161   -0.5169    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3227   -0.7108    0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057   -1.3919    1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9447   -1.4048   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166    2.7122    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    2.9597    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182    1.8602    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606   -1.4142    0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481   -1.5204    0.0979 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  2  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for HMDB0001868 (5-Methoxysalicylic acid)

  Mrv1652305271900002D          

 12 12  0  0  0  0            999 V2000
   18.9347   -6.3195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -3.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0769   -4.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -3.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9347   -7.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -3.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -5.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -4.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -5.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -6.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  8  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  2  0  0  0  0
  6  9  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 10  2  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001868

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C(O)=O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)

> <INCHI_KEY>
IZZIWIAOVZOBLF-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.804565431840857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-5-methoxybenzoic acid

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.8195921366666663

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.23780861467641

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.522487836846782

> <JCHEM_PKA_STRONGEST_BASIC>
-4.819836853933018

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
41.758300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxysalicylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0001868 (5-Methoxysalicylic acid)

HMDB0001868
     RDKit          3D
5-Methoxysalicylic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.2037   -0.8397    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273    0.4508    0.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    0.5850    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635    1.8339    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079    1.9666    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5004    0.8326    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728    0.9559    0.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -0.4493    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131   -1.6237    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401   -2.7826    0.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -1.5025    0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161   -0.5169    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3227   -0.7108    0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057   -1.3919    1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9447   -1.4048   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166    2.7122    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    2.9597    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182    1.8602    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606   -1.4142    0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481   -1.5204    0.0979 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  2  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
 11 19  1  0
 12 20  1  0
M  END
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PDB for HMDB0001868 (5-Methoxysalicylic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      35.345 -11.796   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.011  -6.407   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      30.010  -8.716   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      31.344  -6.407   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      35.345 -13.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.677  -7.177   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.344  -9.486   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.011 -11.027   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.677  -8.716   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.011  -9.486   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.344 -11.027   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.677 -11.796   0.000  0.00  0.00           C+0
CONECT    1    5    8                                                       
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    6                                                            
CONECT    5    1                                                            
CONECT    6    2    4    9                                                  
CONECT    7    3    9   11                                                  
CONECT    8    1   10   12                                                  
CONECT    9    6    7   10                                                  
CONECT   10    8    9                                                       
CONECT   11    7   12                                                       
CONECT   12    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0001868 (5-Methoxysalicylic acid)

COMPND    HMDB0001868
HETATM    1  C1  UNL     1       3.204  -0.840   0.107  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.627   0.451   0.139  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.245   0.585   0.145  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.664   1.834   0.176  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.708   1.967   0.182  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.500   0.833   0.158  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.873   0.956   0.165  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.954  -0.449   0.127  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.813  -1.624   0.102  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.340  -2.783   0.075  1.00  0.00           O  
HETATM   11  O4  UNL     1      -3.191  -1.503   0.109  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.416  -0.517   0.122  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.323  -0.711   0.120  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.906  -1.392   1.024  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.945  -1.405  -0.812  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.317   2.712   0.194  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.136   2.960   0.206  1.00  0.00           H  
HETATM   18  H6  UNL     1      -3.318   1.860   0.187  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.661  -1.414   0.995  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.848  -1.520   0.098  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   16
CONECT    5    6    6   17
CONECT    6    7    8
CONECT    7   18
CONECT    8    9   12   12
CONECT    9   10   10   11
CONECT   11   19
CONECT   12   20
END
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SMILES for HMDB0001868 (5-Methoxysalicylic acid)

COC1=CC(C(O)=O)=C(O)C=C1
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INCHI for HMDB0001868 (5-Methoxysalicylic acid)

InChI=1S/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
5-MeOSAChEBI
5-Methoxy-2-hydroxybenzoic acidChEBI
5-O-Methyl gentisic acidChEBI
6-Hydroxy-m-anisic acidChEBI
Acid5-methoxysalicylicChEBI
5-Methoxy-2-hydroxybenzoateGenerator
5-O-Methyl gentisateGenerator
6-Hydroxy-m-anisateGenerator
5-MethoxysalicylateGenerator
2-Hydroxy-5-methoxybenzoateHMDB, Generator
2-Hydroxy-5-methoxybenzoic acidHMDB
6-Methoxy-m-anisateHMDB
6-Methoxy-m-anisic acidHMDB
5-Methoxysalicylic acid, sodium saltMeSH, HMDB
5-Methoxysalicylic acidMeSH
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-hydroxy-5-methoxybenzoic acid
Traditional Name5-methoxysalicylic acid
CAS Registry Number2612-02-4
SMILES
COC1=CC(C(O)=O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)
InChI KeyIZZIWIAOVZOBLF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • M-methoxybenzoic acid or derivatives
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • 4-alkoxyphenol
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point142 - 146 °CNot Available
Boiling Point347.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility9 mg/mLNot Available
LogP2.100 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Erythrocyte
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
UrineDetected and Quantified0.14 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified8.294 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011959
KNApSAcK IDC00055625
Chemspider ID68296
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Methoxysalicylic_acid
METLIN ID4164
PubChem Compound75787
PDB IDNot Available
ChEBI ID89830
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1210831
References
Synthesis ReferenceNagasawa, Masaaki; Nishioka, Hiroyasu; Suzuki, Takanori; Nagano, Eiichi; Ishii, Katsuyuki; Nakao, Ryu. Preparation of salicylic acids from 2-methoxybenzoic acids. Jpn. Kokai Tokkyo Koho (2000), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nishihata T, Higuchi T, Kamada A: Possible mechanism of uptake for several compounds in ionized form through human erythrocyte membrane. Life Sci. 1984 Jan 30;34(5):427-36. [PubMed:6694531 ]
  2. Nishihata T, Higuchi T, Kamada A: Salicylate-promoted permeation of cefoxitin, insulin and phenylalanine across red cell membrane. Possible mechanism. Life Sci. 1984 Jan 30;34(5):437-45. [PubMed:6319944 ]