Showing metabocard for Phenol (MMDBc0000077)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:29:32 UTC
Update Date2024-09-27 17:00:40 UTC
Metabolite IDMMDBc0000077
Metabolite Identification
Common NamePhenol
DescriptionPhenol, is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe; in laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. Notwithstanding the effects of concentrated solutions, it is also used in cosmetic surgery as an exfoliant, to remove layers of dead skin (Wikipedia ). In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2]. It can be produced by Escherichia and Pseudomonas. Phenol has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f52f9ef2240>

  Mrv1652309272007402D          

  7  7  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    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
  6  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f52f9ef2240>

HMDB0000228
     RDKit          3D
Phenol
 13 13  0  0  0  0  0  0  0  0999 V2000
   -2.4586   -0.1783   -0.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0807   -0.0698   -0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488   -1.2361   -0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0249   -1.1126    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    0.1202    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946    1.2663    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    1.1713   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998   -0.2096    0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8235   -2.2070   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5957   -2.0490    0.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7326    0.1774    0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3565    2.2644    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    2.0628   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  1  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
M  END
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3D SDF for #<Metabolite:0x00007f52f9ef2240>

  Mrv1652309272007402D          

  7  7  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    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
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000077

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H

> <INCHI_KEY>
ISWSIDIOOBJBQZ-UHFFFAOYSA-N

> <FORMULA>
C6H6O

> <MOLECULAR_WEIGHT>
94.1112

> <EXACT_MASS>
94.041864814

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.812560861971921

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
phenol

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.6696804943333332

> <ALOGPS_LOGS>
-0.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.016150276173818

> <JCHEM_PKA_STRONGEST_BASIC>
-5.476712177992348

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
28.038899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f52f9ef2240>

HMDB0000228
     RDKit          3D
Phenol
 13 13  0  0  0  0  0  0  0  0999 V2000
   -2.4586   -0.1783   -0.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0807   -0.0698   -0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488   -1.2361   -0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0249   -1.1126    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    0.1202    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946    1.2663    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    1.1713   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998   -0.2096    0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8235   -2.2070   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5957   -2.0490    0.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7326    0.1774    0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3565    2.2644    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    2.0628   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  1  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
M  END
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PDB for #<Metabolite:0x00007f52f9ef2240>

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       1.083   3.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   1.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083   0.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.417   1.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   2.832   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.750   3.602   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for #<Metabolite:0x00007f52f9ef2240>

COMPND    HMDB0000228
HETATM    1  O1  UNL     1      -2.459  -0.178  -0.342  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.081  -0.070  -0.190  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.349  -1.236  -0.104  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.025  -1.113   0.048  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.655   0.120   0.113  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.895   1.266   0.024  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.472   1.171  -0.127  1.00  0.00           C  
HETATM    8  H1  UNL     1      -3.000  -0.210   0.512  1.00  0.00           H  
HETATM    9  H2  UNL     1      -0.823  -2.207  -0.153  1.00  0.00           H  
HETATM   10  H3  UNL     1       1.596  -2.049   0.114  1.00  0.00           H  
HETATM   11  H4  UNL     1       2.733   0.177   0.232  1.00  0.00           H  
HETATM   12  H5  UNL     1       1.356   2.264   0.071  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.076   2.063  -0.197  1.00  0.00           H  
CONECT    1    2    8
CONECT    2    3    3    7
CONECT    3    4    9
CONECT    4    5    5   10
CONECT    5    6   11
CONECT    6    7    7   12
CONECT    7   13
END
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SMILES for #<Metabolite:0x00007f52f9ef2240>

OC1=CC=CC=C1
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INCHI for #<Metabolite:0x00007f52f9ef2240>

InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
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Synonyms
Molecular FormulaC6H6O
Average Mass94.1112
Monoisotopic Mass94.041864814
IUPAC Namephenol
Traditional Namephenol
CAS Registry Number108-95-2
SMILES
OC1=CC=CC=C1
InChI Identifier
InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
InChI KeyISWSIDIOOBJBQZ-UHFFFAOYSA-N