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Showing metabocard for 4-tert-Butylphenol (HMDB0032063)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:47:32 UTC
Update Date2023-02-21 17:21:35 UTC
HMDB IDHMDB0032063
Secondary Accession Numbers
  • HMDB32063
Metabolite Identification
Common Name4-tert-Butylphenol
Description4-tert-Butylphenol, also known as butylphen or PTBP, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. 4-tert-Butylphenol is a leather and oakmoss tasting compound. 4-tert-Butylphenol has been detected, but not quantified, in herbs and spices. 4-Tert-butylphenol is structurally similar to the melanin precursor tyrosine, and acts as a substrate for tyrosinase. 4-tert-Butylphenol is a potentially toxic compound. Tyrosinase oxidizes 4-tert-butylphenol to a quinone (4-tert-butylcyclohexa-3,5-diene-1,2-dione) which in turn rapidly reacts with glutathione (GSH). A depletion of the GSH defence system may allow the quinone to generate reactive oxygen species that damage melanocytes and induce apoptosis, leading to leukoderma/vitiligo.
Structure
Data?1677000095
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032063 (4-tert-Butylphenol)

  Mrv1652303202019012D          

 11 11  0  0  0  0            999 V2000
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    1.4289    0.8250    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
    0.7145   -1.2375    0.0000 C   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
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
Download

3D MOL for HMDB0032063 (4-tert-Butylphenol)

HMDB0032063
     RDKit          3D
4-tert-Butylphenol
 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.0514    1.0591   -0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3201   -0.1728   -0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2389   -1.1559   -1.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9677   -0.7873    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1045    0.1368   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6003    1.3994   -0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386    1.6129    0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8118    0.5446    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1769    0.7420    0.5770 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101   -0.7555    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.9315    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0123    0.6859   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2764    1.7297   -0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200    1.5698   -1.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -1.0443   -2.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2706   -2.2011   -1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3011   -0.9321   -2.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8553   -1.4087    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3986    0.0054    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -1.3964    1.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0865    2.2264   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260    2.6084    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8111   -0.0245    0.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038   -1.5674    0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5687   -1.9430   -0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
M  END
Download

3D SDF for HMDB0032063 (4-tert-Butylphenol)

  Mrv1652303202019012D          

 11 11  0  0  0  0            999 V2000
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    1.4289    0.8250    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
    0.7145   -1.2375    0.0000 C   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
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032063

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7,11H,1-3H3

> <INCHI_KEY>
QHPQWRBYOIRBIT-UHFFFAOYSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.2176

> <EXACT_MASS>
150.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.64383277226675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-tert-butylphenol

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
3.2147367650000005

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.244785515422764

> <JCHEM_PKA_STRONGEST_BASIC>
-5.446358858902767

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
46.704800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-tert-butylphenol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0032063 (4-tert-Butylphenol)

HMDB0032063
     RDKit          3D
4-tert-Butylphenol
 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.0514    1.0591   -0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3201   -0.1728   -0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2389   -1.1559   -1.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9677   -0.7873    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1045    0.1368   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6003    1.3994   -0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386    1.6129    0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8118    0.5446    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1769    0.7420    0.5770 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101   -0.7555    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.9315    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0123    0.6859   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2764    1.7297   -0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200    1.5698   -1.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -1.0443   -2.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2706   -2.2011   -1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3011   -0.9321   -2.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8553   -1.4087    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3986    0.0054    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -1.3964    1.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0865    2.2264   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260    2.6084    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8111   -0.0245    0.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038   -1.5674    0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5687   -1.9430   -0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
M  END
Download

PDB for HMDB0032063 (4-tert-Butylphenol)

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       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.874  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4    6    8                                                       
CONECT    5    7    8                                                       
CONECT    6    4    9                                                       
CONECT    7    5    9                                                       
CONECT    8    4    5   10                                                  
CONECT    9    6    7   11                                                  
CONECT   10    1    2    3    8                                             
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0032063 (4-tert-Butylphenol)

COMPND    HMDB0032063
HETATM    1  C1  UNL     1      -2.051   1.059  -0.884  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.320  -0.173  -0.413  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.239  -1.156  -1.595  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.968  -0.787   0.775  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.105   0.137  -0.094  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.600   1.399  -0.000  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.939   1.613   0.227  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.812   0.545   0.360  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.177   0.742   0.577  1.00  0.00           O  
HETATM   10  C9  UNL     1       2.310  -0.755   0.270  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.969  -0.932   0.043  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.012   0.686  -1.306  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.276   1.730  -0.037  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.520   1.570  -1.697  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.092  -1.044  -2.283  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.271  -2.201  -1.213  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.301  -0.932  -2.176  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.855  -1.409   0.490  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.399   0.005   1.441  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.230  -1.396   1.361  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.087   2.226  -0.092  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.326   2.608   0.323  1.00  0.00           H  
HETATM   23  H12 UNL     1       4.811  -0.024   0.658  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.004  -1.567   0.422  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.569  -1.943  -0.062  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    5
CONECT    3   15   16   17
CONECT    4   18   19   20
CONECT    5    6    6   11
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9   10
CONECT    9   23
CONECT   10   11   11   24
CONECT   11   25
END
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SMILES for HMDB0032063 (4-tert-Butylphenol)

CC(C)(C)C1=CC=C(O)C=C1
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INCHI for HMDB0032063 (4-tert-Butylphenol)

InChI=1S/C10H14O/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7,11H,1-3H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name4-tert-butylphenol
Traditional Name4-tert-butylphenol
CAS Registry Number98-54-4
SMILES
CC(C)(C)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C10H14O/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7,11H,1-3H3
InChI KeyQHPQWRBYOIRBIT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point99 °CNot Available
Boiling Point237.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.58 mg/mL at 25 °CNot Available
LogP3.31Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Bothautism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
Associated Disorders and Diseases
Disease References
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008772
KNApSAcK IDC00045799
Chemspider ID13846663
KEGG Compound IDC14200
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7393
PDB IDNot Available
ChEBI ID34444
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1013761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .