Showing metabocard for Salicylic acid (MMDBc0000777)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:54:43 UTC
Update Date2024-09-27 18:28:58 UTC
Metabolite IDMMDBc0000777
Metabolite Identification
Common NameSalicylic acid
DescriptionSalicylic acid is a monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. It is obtained from the bark of the white willow and wintergreen leaves. It has a role as an antiinfective agent, an antifungal agent, a keratolytic drug, an EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor, a plant metabolite, an algal metabolite and a plant hormone. It is a conjugate acid of a salicylate. It is a colorless solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone. The name is from Latin salix for willow tree. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates. Salicylic acid modulates COX1 enzymatic activity to decrease the formation of pro-inflammatory prostaglandins. Salicylate may competitively inhibit prostaglandin formation. Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. Salicylic acid works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis. Salicylic acid is biosynthesized from the amino acid phenylalanine. In Arabidopsis thaliana, it can be synthesized via a phenylalanine-independent pathway.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f46d90fd058>


  Mrv1652309272007452D          

 10 10  0  0  0  0            999 V2000
   -0.7810   -0.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954   -0.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -1.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4955   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7810   -1.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954    0.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0665   -0.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0666    0.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -0.5248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  2  7  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f46d90fd058>

HMDB0001895
     RDKit          3D
Salicylic acid
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.6574    0.9644   -0.1551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489   -0.1207    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7988   -1.2480    0.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5771   -0.1402   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1224   -1.3130    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -1.3373    0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -0.1621   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860    1.0109   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086    1.0339   -0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5897    2.2413   -0.4252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5489   -1.3137    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4617   -2.2300    0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -2.2754    0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717   -0.1472   -0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259    1.9549   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516    3.0823   -0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
 10 16  1  0
M  END
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3D SDF for #<Metabolite:0x00007f46d90fd058>


  Mrv1652309272007452D          

 10 10  0  0  0  0            999 V2000
   -0.7810   -0.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954   -0.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -1.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4955   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7810   -1.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954    0.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0665   -0.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0666    0.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -0.5248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  2  7  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000777

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)

> <INCHI_KEY>
YGSDEFSMJLZEOE-UHFFFAOYSA-N

> <FORMULA>
C7H6O3

> <MOLECULAR_WEIGHT>
138.122

> <EXACT_MASS>
138.031694053

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.814587378025518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxybenzoic acid

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
1.977263402333333

> <ALOGPS_LOGS>
-1.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.228682517040586

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7897391795725692

> <JCHEM_PKA_STRONGEST_BASIC>
-6.285929432184692

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
35.2951

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salicylic

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f46d90fd058>

HMDB0001895
     RDKit          3D
Salicylic acid
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.6574    0.9644   -0.1551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489   -0.1207    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7988   -1.2480    0.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5771   -0.1402   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1224   -1.3130    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -1.3373    0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -0.1621   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860    1.0109   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086    1.0339   -0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5897    2.2413   -0.4252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5489   -1.3137    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4617   -2.2300    0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -2.2754    0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717   -0.1472   -0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259    1.9549   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516    3.0823   -0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
 10 16  1  0
M  END
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PDB for #<Metabolite:0x00007f46d90fd058>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.458  -0.980   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.791  -0.210   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.125  -0.980   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.125  -2.520   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.792  -3.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.458  -2.520   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.791   1.330   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.124  -0.210   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.124   1.330   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.209  -0.980   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for #<Metabolite:0x00007f46d90fd058>

COMPND    HMDB0001895
HETATM    1  O1  UNL     1      -2.657   0.964  -0.155  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.049  -0.121   0.023  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.799  -1.248   0.239  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.577  -0.140  -0.005  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.122  -1.313   0.187  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.500  -1.337   0.162  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.184  -0.162  -0.061  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.486   1.011  -0.253  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.109   1.034  -0.227  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.590   2.241  -0.425  1.00  0.00           O  
HETATM   11  H1  UNL     1      -3.549  -1.314   0.941  1.00  0.00           H  
HETATM   12  H2  UNL     1      -0.462  -2.230   0.362  1.00  0.00           H  
HETATM   13  H3  UNL     1       2.036  -2.275   0.316  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.272  -0.147  -0.087  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.026   1.955  -0.431  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.052   3.082  -0.585  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5    9
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8   14
CONECT    8    9    9   15
CONECT    9   10
CONECT   10   16
END
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SMILES for #<Metabolite:0x00007f46d90fd058>

OC(=O)C1=C(O)C=CC=C1
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INCHI for #<Metabolite:0x00007f46d90fd058>

InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
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Synonyms
ValueSource
2-CarboxyphenolChEBI
2-HYDROXYBENZOIC ACIDChEBI
O-CarboxyphenolChEBI
O-Hydroxybenzoic acidChEBI
2-HYDROXYBENZOateGenerator
O-HydroxybenzoateGenerator
SalicylateGenerator
2 Hydroxybenzoic acidMeSH
Acid, 2-hydroxybenzoicMeSH
Acid, salicylicMeSH
Acid, O-hydroxybenzoicMeSH
Acid, ortho-hydroxybenzoicMeSH
O Hydroxybenzoic acidMeSH
Ortho hydroxybenzoic acidMeSH
Ortho-hydroxybenzoic acidMeSH
2-HydroxybenzenecarboxylateHMDB
2-Hydroxybenzenecarboxylic acidHMDB
Advanced pain relief callus removersHMDB
Advanced pain relief corn removersHMDB
Clear away wart removerHMDB
Compound WHMDB
Dr. scholl's callus removersHMDB
Dr. scholl's corn removersHMDB
Dr. scholl's wart remover kitHMDB
Duofil wart removerHMDB
DuoplantHMDB
FreezoneHMDB
IonilHMDB
Ionil plusHMDB
K 537HMDB
K 557HMDB
Phenol-2-carboxylateHMDB
Phenol-2-carboxylic acidHMDB
Psoriacid-S-stiftHMDB
Retarder WHMDB
RutranexHMDB
Salicylic acid collodionHMDB
Salicylic acid soapHMDB
SaligelHMDB
SalonilHMDB
Stri-dexHMDB
trans-Ver-salHMDB
SAPhytoBank
Molecular FormulaC7H6O3
Average Mass138.122
Monoisotopic Mass138.031694053
IUPAC Name2-hydroxybenzoic acid
Traditional Namesalicylic
CAS Registry NumberNot Available
SMILES
OC(=O)C1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
InChI KeyYGSDEFSMJLZEOE-UHFFFAOYSA-N