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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:51 UTC
Update Date2020-02-26 21:39:21 UTC
HMDB IDHMDB0014018
Secondary Accession Numbers
  • HMDB14018
Metabolite Identification
Common Name4-Hydroxypropofol
Description4-Hydroxypropofol belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. 4-Hydroxypropofol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-Hydroxypropofol.
Structure
Data?1582753161
Synonyms
ValueSource
2,6-Bis(1-methylethyl)-1,4-benzenediolChEBI
2,6-Bis(propan-2-yl)benzene-1,4-diolChEBI
2,6-Diisopropyl-1,4-benzenediolChEBI
2,6-Diisopropylbenzene-1,4-diolChEBI
2,6-DiisopropylhydroquinoneChEBI
Chemical FormulaC12H18O2
Average Molecular Weight194.2701
Monoisotopic Molecular Weight194.13067982
IUPAC Name2,6-bis(propan-2-yl)benzene-1,4-diol
Traditional Name2,6-diisopropylbenzene-1,4-diol
CAS Registry NumberNot Available
SMILES
CC(C)C1=CC(O)=CC(C(C)C)=C1O
InChI Identifier
InChI=1S/C12H18O2/c1-7(2)10-5-9(13)6-11(8(3)4)12(10)14/h5-8,13-14H,1-4H3
InChI KeyUFWIJKBKROBWTG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassCumenes
Direct ParentCumenes
Alternative Parents
Substituents
  • Phenylpropane
  • Cumene
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
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
Water Solubility0.99 g/LALOGPS
logP2.99ALOGPS
logP3.86ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.09ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.4 m³·mol⁻¹ChemAxon
Polarizability22.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.25931661259
DarkChem[M-H]-141.59531661259
DeepCCS[M+H]+150.47730932474
DeepCCS[M-H]-148.11930932474
DeepCCS[M-2H]-182.77630932474
DeepCCS[M+Na]+158.31130932474
AllCCS[M+H]+142.132859911
AllCCS[M+H-H2O]+138.032859911
AllCCS[M+NH4]+145.932859911
AllCCS[M+Na]+147.032859911
AllCCS[M-H]-146.832859911
AllCCS[M+Na-2H]-147.732859911
AllCCS[M+HCOO]-148.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxypropofolCC(C)C1=CC(O)=CC(C(C)C)=C1O2292.8Standard polar33892256
4-HydroxypropofolCC(C)C1=CC(O)=CC(C(C)C)=C1O1562.0Standard non polar33892256
4-HydroxypropofolCC(C)C1=CC(O)=CC(C(C)C)=C1O1664.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxypropofol,1TMS,isomer #1CC(C)C1=CC(O[Si](C)(C)C)=CC(C(C)C)=C1O1572.6Semi standard non polar33892256
4-Hydroxypropofol,1TMS,isomer #2CC(C)C1=CC(O)=CC(C(C)C)=C1O[Si](C)(C)C1652.6Semi standard non polar33892256
4-Hydroxypropofol,2TMS,isomer #1CC(C)C1=CC(O[Si](C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C1636.7Semi standard non polar33892256
4-Hydroxypropofol,1TBDMS,isomer #1CC(C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O1825.0Semi standard non polar33892256
4-Hydroxypropofol,1TBDMS,isomer #2CC(C)C1=CC(O)=CC(C(C)C)=C1O[Si](C)(C)C(C)(C)C1868.2Semi standard non polar33892256
4-Hydroxypropofol,2TBDMS,isomer #1CC(C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C(C)(C)C2093.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxypropofol GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-1900000000-0acaadf3b241ed7ab1652017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxypropofol GC-MS (2 TMS) - 70eV, Positivesplash10-00di-7098000000-2de0b0eab913992877de2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxypropofol 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 - 4-Hydroxypropofol 10V, Positive-QTOFsplash10-0002-0900000000-3efadb5ddb8ced1137ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 20V, Positive-QTOFsplash10-0f6t-1900000000-5abbefcd14f558b75f042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 40V, Positive-QTOFsplash10-066r-9400000000-e4832174f4e77dcadaca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 10V, Negative-QTOFsplash10-0006-0900000000-e37d4f27ca4fb72868ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 20V, Negative-QTOFsplash10-0006-0900000000-0fbef986586ffbfec4592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 40V, Negative-QTOFsplash10-0hgo-6900000000-5301908ab3abb37833c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 10V, Positive-QTOFsplash10-0002-0900000000-8ba12c31a110cd8aedcb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 20V, Positive-QTOFsplash10-0005-1900000000-cfd90a4374b9ddf571a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 40V, Positive-QTOFsplash10-014i-9400000000-2a20d873e35a972f1cf82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 10V, Negative-QTOFsplash10-0006-0900000000-c3ede4c1eb6b090e0d1d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 20V, Negative-QTOFsplash10-0006-0900000000-f88b4e8ab5993cd5b2622021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxypropofol 40V, Negative-QTOFsplash10-014i-9400000000-2ad7782232350425ea6b2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry 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 ID2282600
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3014064
PDB IDNot Available
ChEBI ID145211
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 ReferencesNot Available

Only showing the first 10 proteins. There are 21 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
References
  1. Mano Y, Usui T, Kamimura H: Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol. 2007 Sep;101(3):211-4. [PubMed:17697043 ]
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Takahashi H, Maruo Y, Mori A, Iwai M, Sato H, Takeuchi Y: Effect of D256N and Y483D on propofol glucuronidation by human uridine 5'-diphosphate glucuronosyltransferase (UGT1A9). Basic Clin Pharmacol Toxicol. 2008 Aug;103(2):131-6. doi: 10.1111/j.1742-7843.2008.00247.x. [PubMed:18816295 ]
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular weight:
59741.035
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215
References
  1. Gu J, Lu K, Xia P, Tang M, Dai Q, Ma D, Tao G: Pharmacokinetics of propofol and extrahepatic UGT1A6 gene expression in anhepatic rats. Pharmacology. 2009;84(4):219-26. doi: 10.1159/000236523. Epub 2009 Sep 10. [PubMed:19752585 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. Chen TL, Ueng TH, Chen SH, Lee PH, Fan SZ, Liu CC: Human cytochrome P450 mono-oxygenase system is suppressed by propofol. Br J Anaesth. 1995 May;74(5):558-62. [PubMed:7772432 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
References
  1. Chen TL, Ueng TH, Chen SH, Lee PH, Fan SZ, Liu CC: Human cytochrome P450 mono-oxygenase system is suppressed by propofol. Br J Anaesth. 1995 May;74(5):558-62. [PubMed:7772432 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Only showing the first 10 proteins. There are 21 proteins in total.