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Showing metabocard for Cumene hydroperoxide (HMDB0250588)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:40:50 UTC
Update Date2021-10-01 19:54:32 UTC
HMDB IDHMDB0250588
Secondary Accession NumbersNone
Metabolite Identification
Common NameCumene hydroperoxide
Description This compound has been identified in human blood as reported by (PMID: 31557052 ). Cumene hydroperoxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cumene 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 HMDB0250588 (Cumene hydroperoxide)

Structure #1
  Mrv0541 02241207192D          

 11 11  0  0  0  0            999 V2000
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    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
    0.0000    0.0000    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    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for HMDB0250588 (Cumene hydroperoxide)

HMDB0250588
     RDKit          3D
Cumene hydroperoxide
 23 23  0  0  0  0  0  0  0  0999 V2000
   -1.7230   -0.3991    1.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    0.1559    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905   -0.5601   -1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    1.5084   -0.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6065    1.8140   -0.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4007   -0.0019    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2027    0.9816   -0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872    0.9181   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1765   -0.2014    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3758   -1.1741    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882   -1.1042    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255    0.0794    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -0.2602    2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9445   -1.4935    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963   -0.2635   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676   -0.3164   -1.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292   -1.6594   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8382    2.5638    0.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    1.8702   -0.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836    1.7209   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575   -0.2118    0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370   -2.0457    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3922   -1.9211    1.0605 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
  4  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  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
  5 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
M  END
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3D SDF for HMDB0250588 (Cumene hydroperoxide)

Structure #1
  Mrv0541 02241207192D          

 11 11  0  0  0  0            999 V2000
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    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
    0.0000    0.0000    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    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250588

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3

> <INCHI_KEY>
YQHLDYVWEZKEOX-UHFFFAOYSA-N

> <FORMULA>
C9H12O2

> <MOLECULAR_WEIGHT>
152.1904

> <EXACT_MASS>
152.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.336105039301128

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-phenylpropane-2-peroxol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.3523831189999997

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.69756459054184

> <JCHEM_PKA_STRONGEST_BASIC>
-4.243285248097014

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
43.2811

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cumene hydroperoxide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0250588 (Cumene hydroperoxide)

HMDB0250588
     RDKit          3D
Cumene hydroperoxide
 23 23  0  0  0  0  0  0  0  0999 V2000
   -1.7230   -0.3991    1.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    0.1559    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905   -0.5601   -1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    1.5084   -0.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6065    1.8140   -0.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4007   -0.0019    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2027    0.9816   -0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872    0.9181   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1765   -0.2014    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3758   -1.1741    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882   -1.1042    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255    0.0794    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -0.2602    2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9445   -1.4935    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963   -0.2635   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676   -0.3164   -1.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292   -1.6594   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8382    2.5638    0.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    1.8702   -0.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836    1.7209   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575   -0.2118    0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370   -2.0457    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3922   -1.9211    1.0605 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
  4  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  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
  5 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
M  END
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PDB for HMDB0250588 (Cumene hydroperoxide)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.874   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7    9                                                  
CONECT    9    1    2    8   11                                             
CONECT   10   11                                                            
CONECT   11    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0250588 (Cumene hydroperoxide)

COMPND    HMDB0250588
HETATM    1  C1  UNL     1      -1.723  -0.399   1.265  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.077   0.156   0.010  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.591  -0.560  -1.209  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.345   1.508  -0.143  1.00  0.00           O  
HETATM    5  O2  UNL     1      -2.607   1.814  -0.229  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.401  -0.002   0.054  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.203   0.982  -0.480  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.587   0.918  -0.475  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.176  -0.201   0.100  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.376  -1.174   0.628  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.988  -1.104   0.621  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.725   0.079   1.423  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.137  -0.260   2.170  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.944  -1.493   1.147  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.996  -0.264  -2.099  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.668  -0.316  -1.422  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.529  -1.659  -1.016  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.838   2.564   0.413  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.779   1.870  -0.940  1.00  0.00           H  
HETATM   20  H9  UNL     1       3.184   1.721  -0.901  1.00  0.00           H  
HETATM   21  H10 UNL     1       4.257  -0.212   0.093  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.837  -2.046   1.083  1.00  0.00           H  
HETATM   23  H12 UNL     1       0.392  -1.921   1.060  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    6
CONECT    3   15   16   17
CONECT    4    5
CONECT    5   18
CONECT    6    7    7   11
CONECT    7    8   19
CONECT    8    9    9   20
CONECT    9   10   21
CONECT   10   11   11   22
CONECT   11   23
END
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SMILES for HMDB0250588 (Cumene hydroperoxide)

CC(C)(OO)C1=CC=CC=C1
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INCHI for HMDB0250588 (Cumene hydroperoxide)

InChI=1S/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC9H12O2
Average Molecular Weight152.1904
Monoisotopic Molecular Weight152.083729628
IUPAC Name2-phenylpropane-2-peroxol
Traditional Namecumene hydroperoxide
CAS Registry NumberNot Available
SMILES
CC(C)(OO)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3
InChI KeyYQHLDYVWEZKEOX-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
  • Hydroperoxide
  • Alkyl hydroperoxide
  • Peroxol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
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
Predicted Chromatographic Properties
Spectra
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD0-1449
BiGG IDNot Available
Wikipedia LinkCumene_hydroperoxide
METLIN IDNot Available
PubChem Compound6629
PDB IDNot Available
ChEBI ID78673
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 S-transferase theta-1
General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Acts on 1,2-epoxy-3-(4-nitrophenoxy)propane, phenethylisothiocyanate 4-nitrobenzyl chloride and 4-nitrophenethyl bromide. Displays glutathione peroxidase activity with cumene hydroperoxide.
Gene Name:
GSTT1
Uniprot ID:
P30711
Molecular weight:
27334.755
Enzyme Details
2. 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
Enzyme Details
3. Hematopoietic prostaglandin D synthase
General function:
Involved in glutathione transferase activity
Specific function:
Bifunctional enzyme which catalyzes both the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation, and the conjugation of glutathione with a wide range of aryl halides and organic isothiocyanates. Also exhibits low glutathione-peroxidase activity towards cumene hydroperoxide.
Gene Name:
HPGDS
Uniprot ID:
O60760
Molecular weight:
23343.65
Enzyme Details
4. Glutathione S-transferase theta-2
General function:
Not Available
Specific function:
Catalyzes the inactivation of reactive sulfate esters in carcinogenic arylmethanols. Highest activity towards ethacrynic acid and cumene hydroperoxide.
Gene Name:
GSTT2
Uniprot ID:
P30713
Molecular weight:
27438.755
Enzyme Details
5. Hematopoietic prostaglandin D synthase
General function:
Not Available
Specific function:
Bifunctional enzyme which catalyzes both the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation, and the conjugation of glutathione with a wide range of aryl halides and organic isothiocyanates. Also exhibits low glutathione-peroxidase activity towards cumene hydroperoxide.
Gene Name:
HPGDS
Uniprot ID:
O35543
Molecular weight:
23296.73