Showing metabocard for gentisyl alcohol (MMDBc0054495)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 23:15:38 UTC
Update Date2025-10-07 16:08:32 UTC
Metabolite IDMMDBc0054495
Metabolite Identification
Common Namegentisyl alcohol
DescriptionGentisyl alcohol is a phenolic compound classified as a secondary metabolite. Its chemical structure features a hydroxyl group attached to a benzene ring, specifically ortho to a hydroxymethyl group, distinguishing it within the class of phenolic alcohols. Gentisyl alcohol is involved in various biochemical pathways, notably as an inhibitor of dihydroorotate dehydrogenase in Plasmodium falciparum, showcasing its potential as an antimalarial agent (PMID:33814517 ). Additionally, it has been identified as part of the biosynthetic pathway of the mycotoxin patulin, alongside other metabolites like toluquinol (PMID:37583517 ). Gentisyl alcohol exhibits significant biological activities, including antibacterial, antifungal, antiviral, and anti-cancer effects, influencing cellular processes such as apoptosis and proliferation in cancer cells through mitochondrial dysfunction and modulation of the MAPK and PI3K/AKT signaling pathways (PMID:31163640 ). Its presence in various fungi, including Aspergillus and Penicillium species, further underscores its ecological and pharmacological relevance (PMID:33814517 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9aada8fad0>


  Mrv1652310091711322D          

 10 10  0  0  0  0            999 V2000
    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
    0.0000   -0.0000    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    0.8250    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
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
  2  1  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  1  2  0  0  0  0
  6  3  1  0  0  0  0
  7  2  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9aada8fad0>

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3D SDF for #<Metabolite:0x00007f9aada8fad0>

  Mrv1652310091711322D          

 10 10  0  0  0  0            999 V2000
    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
    0.0000   -0.0000    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    0.8250    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
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
  2  1  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  1  2  0  0  0  0
  6  3  1  0  0  0  0
  7  2  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054495

> <DATABASE_NAME>
MIME

> <SMILES>
OCC1=CC(O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O3/c8-4-5-3-6(9)1-2-7(5)10/h1-3,8-10H,4H2

> <INCHI_KEY>
PUZSUVGRVHEUQO-UHFFFAOYSA-N

> <FORMULA>
C7H8O3

> <MOLECULAR_WEIGHT>
140.138

> <EXACT_MASS>
140.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.693377623889106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)benzene-1,4-diol

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
0.5987654053333333

> <ALOGPS_LOGS>
-0.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.745563053936012

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.720024764781542

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9568217452836736

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
36.835699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.65e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gentisyl alcohol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9aada8fad0>
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PDB for #<Metabolite:0x00007f9aada8fad0>
HEADER    PROTEIN                                 09-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-OCT-17         0                                  
HETATM    1  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    5    6                                                       
CONECT    4    5    8                                                       
CONECT    5    3    4    7                                                  
CONECT    6    1    3    9                                                  
CONECT    7    2    5   10                                                  
CONECT    8    4                                                            
CONECT    9    6                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for #<Metabolite:0x00007f9aada8fad0>
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SMILES for #<Metabolite:0x00007f9aada8fad0>
OCC1=CC(O)=CC=C1O
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INCHI for #<Metabolite:0x00007f9aada8fad0>
InChI=1S/C7H8O3/c8-4-5-3-6(9)1-2-7(5)10/h1-3,8-10H,4H2
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Synonyms
ValueSource
2,5-Dihydroxybenzyl alcoholKegg
2,5-Dihydroxybenzyl alcohol, sodium saltMeSH
3,6-Dihydroxybenzyl alcoholMeSH
Molecular FormulaC7H8O3
Average Mass140.138
Monoisotopic Mass140.047344118
IUPAC Name2-(hydroxymethyl)benzene-1,4-diol
Traditional Namegentisyl alcohol
CAS Registry NumberNot Available
SMILES
OCC1=CC(O)=CC=C1O
InChI Identifier
InChI=1S/C7H8O3/c8-4-5-3-6(9)1-2-7(5)10/h1-3,8-10H,4H2
InChI KeyPUZSUVGRVHEUQO-UHFFFAOYSA-N