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Showing metabocard for Tert-butyl hydroperoxide (HMDB0258844)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 20:37:35 UTC
Update Date2021-09-26 23:16:02 UTC
HMDB IDHMDB0258844
Secondary Accession NumbersNone
Metabolite Identification
Common NameTert-butyl hydroperoxide
Descriptiontert-butyl hydroperoxide, also known as dimethylethyl hydroperoxide or TBHP, belongs to the class of organic compounds known as organic hydroperoxides. These are organic compounds comprising the hydroperoxide functional group, with the general formula [O-O]2-. Based on a literature review a significant number of articles have been published on tert-butyl hydroperoxide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tert-butyl hydroperoxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tert-butyl hydroperoxide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0258844 (Tert-butyl hydroperoxide)


  Mrv1572004191604152D          

  6  5  0  0  0  0            999 V2000
   -0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
M  END
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3D MOL for HMDB0258844 (Tert-butyl hydroperoxide)

HMDB0258844
     RDKit          3D
Tert-butyl hydroperoxide
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.1071   -0.4097   -1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390    0.0180   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847    1.4118    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0382   -0.9729    1.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841   -0.0530   -0.8890 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727    0.2788   -0.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8721   -1.4209   -1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0163   -0.3798   -0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    0.3399   -1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5653    2.0829    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1803    1.8383   -0.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4735    1.4684    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0221   -1.1877    1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.6035    1.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4489   -1.9296    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234   -0.4811   -0.4101 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  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  4 15  1  0
  6 16  1  0
M  END
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3D SDF for HMDB0258844 (Tert-butyl hydroperoxide)


  Mrv1572004191604152D          

  6  5  0  0  0  0            999 V2000
   -0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258844

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)OO

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3

> <INCHI_KEY>
CIHOLLKRGTVIJN-UHFFFAOYSA-N

> <FORMULA>
C4H10O2

> <MOLECULAR_WEIGHT>
90.122

> <EXACT_MASS>
90.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
9.747245254128531

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpropane-2-peroxol

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
0.9847179563333335

> <ALOGPS_LOGS>
0.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.719380378428962

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2337430224751875

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
23.4171

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tert-butyl hydroperoxide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0258844 (Tert-butyl hydroperoxide)

HMDB0258844
     RDKit          3D
Tert-butyl hydroperoxide
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.1071   -0.4097   -1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390    0.0180   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847    1.4118    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0382   -0.9729    1.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841   -0.0530   -0.8890 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727    0.2788   -0.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8721   -1.4209   -1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0163   -0.3798   -0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    0.3399   -1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5653    2.0829    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1803    1.8383   -0.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4735    1.4684    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0221   -1.1877    1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.6035    1.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4489   -1.9296    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234   -0.4811   -0.4101 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  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  4 15  1  0
  6 16  1  0
M  END
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PDB for HMDB0258844 (Tert-butyl hydroperoxide)

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.104   0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    4                                                            
CONECT    4    1    2    3    6                                             
CONECT    5    6                                                            
CONECT    6    4    5                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0258844 (Tert-butyl hydroperoxide)

COMPND    HMDB0258844
HETATM    1  C1  UNL     1      -1.107  -0.410  -1.049  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.039   0.018  -0.133  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.285   1.412   0.339  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.038  -0.973   1.028  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.184  -0.053  -0.889  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.273   0.279  -0.269  1.00  0.00           O  
HETATM    7  H1  UNL     1      -0.872  -1.421  -1.434  1.00  0.00           H  
HETATM    8  H2  UNL     1      -2.016  -0.380  -0.416  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.133   0.340  -1.868  1.00  0.00           H  
HETATM   10  H4  UNL     1       0.565   2.083   0.029  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.180   1.838  -0.155  1.00  0.00           H  
HETATM   12  H6  UNL     1      -0.474   1.468   1.431  1.00  0.00           H  
HETATM   13  H7  UNL     1      -1.022  -1.188   1.279  1.00  0.00           H  
HETATM   14  H8  UNL     1       0.618  -0.603   1.891  1.00  0.00           H  
HETATM   15  H9  UNL     1       0.449  -1.930   0.626  1.00  0.00           H  
HETATM   16  H10 UNL     1       2.923  -0.481  -0.410  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4    5
CONECT    3   10   11   12
CONECT    4   13   14   15
CONECT    5    6
CONECT    6   16
END
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SMILES for HMDB0258844 (Tert-butyl hydroperoxide)

CC(C)(C)OO
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INCHI for HMDB0258844 (Tert-butyl hydroperoxide)

InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,1-Dimethylethyl hydroperoxideChEBI
2-Hydroperoxy-2-methylpropaneChEBI
Dimethylethyl hydroperoxideChEBI
Hydroperoxyde de butyle tertiaireChEBI
t-Butyl hydroperoxideChEBI
t-ButylhydroperoxideChEBI
TBHPChEBI
Tert-butylhydroperoxideChEBI
Tertiary-butyl hydroperoxideChEBI
Tert butylhydroperoxideMeSH
Hydroperoxide, t-butylMeSH
Tert butyl hydroperoxideMeSH
Hydroperoxide, tert-butylMeSH
t ButylhydroperoxideMeSH
Tertiary butylhydroperoxideMeSH
Tert-butyl hydroperoxideMeSH
Tertiary-butylhydroperoxideMeSH
t Butyl hydroperoxideMeSH
Chemical FormulaC4H10O2
Average Molecular Weight90.122
Monoisotopic Molecular Weight90.068079562
IUPAC Name2-methylpropane-2-peroxol
Traditional Nametert-butyl hydroperoxide
CAS Registry NumberNot Available
SMILES
CC(C)(C)OO
InChI Identifier
InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3
InChI KeyCIHOLLKRGTVIJN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic hydroperoxides. These are organic compounds comprising the hydroperoxide functional group, with the general formula [O-O]2-.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic hydroperoxides
Sub ClassNot Available
Direct ParentOrganic hydroperoxides
Alternative Parents
Substituents
  • Hydroperoxide
  • Alkyl hydroperoxide
  • Peroxol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.92ALOGPS
logP0.98ChemAxon
logS0.29ALOGPS
pKa (Strongest Acidic)11.72ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.42 m³·mol⁻¹ChemAxon
Polarizability9.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+124.83330932474
DeepCCS[M-H]-122.93730932474
DeepCCS[M-2H]-158.53430932474
DeepCCS[M+Na]+133.07130932474
AllCCS[M+H]+124.432859911
AllCCS[M+H-H2O]+120.332859911
AllCCS[M+NH4]+128.332859911
AllCCS[M+Na]+129.432859911
AllCCS[M-H]-125.832859911
AllCCS[M+Na-2H]-130.732859911
AllCCS[M+HCOO]-136.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tert-butyl hydroperoxideCC(C)(C)OO1173.4Standard polar33892256
Tert-butyl hydroperoxideCC(C)(C)OO648.9Standard non polar33892256
Tert-butyl hydroperoxideCC(C)(C)OO616.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tert-butyl hydroperoxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a7l-9000000000-29f1a51990e028187cf72021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tert-butyl hydroperoxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tert-butyl hydroperoxide 10V, Negative-QTOFsplash10-000i-9000000000-9636f2985582560d20cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tert-butyl hydroperoxide 20V, Negative-QTOFsplash10-000i-9000000000-ce82a78b5394d048b0c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tert-butyl hydroperoxide 40V, Negative-QTOFsplash10-0079-9000000000-c1c00e6873972f5da7522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tert-butyl hydroperoxide 10V, Positive-QTOFsplash10-0006-9000000000-c2032a883c085c3ecf1e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tert-butyl hydroperoxide 20V, Positive-QTOFsplash10-0a4u-9000000000-f03fb4a44c370afd022a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tert-butyl hydroperoxide 40V, Positive-QTOFsplash10-054o-9000000000-3bcf056cc22026facec72016-08-02Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6170
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTert-Butyl_hydroperoxide
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID64090
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1285961
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details
1. Glutathione peroxidase 2
General function:
Involved in glutathione peroxidase activity
Specific function:
Could play a major role in protecting mammals from the toxicity of ingested organic hydroperoxides. Tert-butyl hydroperoxide, cumene hydroperoxide and linoleic acid hydroperoxide but not phosphatidycholine hydroperoxide, can act as acceptors.
Gene Name:
GPX2
Uniprot ID:
P18283
Molecular weight:
21953.835