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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:19:30 UTC
Update Date2021-09-26 23:01:43 UTC
HMDB IDHMDB0250320
Secondary Accession NumbersNone
Metabolite Identification
Common NameCletoquine
Description2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}amino)ethan-1-ol belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system. Based on a literature review very few articles have been published on 2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}amino)ethan-1-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cletoquine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cletoquine 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
Thumb
Synonyms
ValueSource
DesethylhydroxychloroquineMeSH
Chemical FormulaC16H22ClN3O
Average Molecular Weight307.82
Monoisotopic Molecular Weight307.14514
IUPAC Name2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}amino)ethan-1-ol
Traditional Name2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}amino)ethanol
CAS Registry NumberNot Available
SMILES
CC(CCCNCCO)NC1=C2C=CC(Cl)=CC2=NC=C1
InChI Identifier
InChI=1S/C16H22ClN3O/c1-12(3-2-7-18-9-10-21)20-15-6-8-19-16-11-13(17)4-5-14(15)16/h4-6,8,11-12,18,21H,2-3,7,9-10H2,1H3,(H,19,20)
InChI KeyXFICNUNWUREFDP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct Parent4-aminoquinolines
Alternative Parents
Substituents
  • 4-aminoquinoline
  • Haloquinoline
  • Chloroquinoline
  • Aminopyridine
  • Secondary aliphatic/aromatic amine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Alkanolamine
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP2.99ALOGPS
logP2.15ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)15.6ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area57.18 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity87.92 m³·mol⁻¹ChemAxon
Polarizability34.3 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+171.23630932474
DeepCCS[M-H]-168.87830932474
DeepCCS[M-2H]-201.76430932474
DeepCCS[M+Na]+177.32930932474
AllCCS[M+H]+172.432859911
AllCCS[M+H-H2O]+169.432859911
AllCCS[M+NH4]+175.132859911
AllCCS[M+Na]+175.932859911
AllCCS[M-H]-173.332859911
AllCCS[M+Na-2H]-173.732859911
AllCCS[M+HCOO]-174.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CletoquineCC(CCCNCCO)NC1=C2C=CC(Cl)=CC2=NC=C13740.8Standard polar33892256
CletoquineCC(CCCNCCO)NC1=C2C=CC(Cl)=CC2=NC=C12813.1Standard non polar33892256
CletoquineCC(CCCNCCO)NC1=C2C=CC(Cl)=CC2=NC=C12883.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cletoquine,2TMS,isomer #1CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C122808.9Semi standard non polar33892256
Cletoquine,2TMS,isomer #1CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C122731.7Standard non polar33892256
Cletoquine,2TMS,isomer #1CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C123421.9Standard polar33892256
Cletoquine,2TMS,isomer #2CC(CCCNCCO[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C2574.1Semi standard non polar33892256
Cletoquine,2TMS,isomer #2CC(CCCNCCO[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C2669.4Standard non polar33892256
Cletoquine,2TMS,isomer #2CC(CCCNCCO[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C3213.0Standard polar33892256
Cletoquine,2TMS,isomer #3CC(CCCN(CCO)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C2749.1Semi standard non polar33892256
Cletoquine,2TMS,isomer #3CC(CCCN(CCO)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C2733.8Standard non polar33892256
Cletoquine,2TMS,isomer #3CC(CCCN(CCO)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C3378.4Standard polar33892256
Cletoquine,3TMS,isomer #1CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C2764.5Semi standard non polar33892256
Cletoquine,3TMS,isomer #1CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C2761.5Standard non polar33892256
Cletoquine,3TMS,isomer #1CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C3129.4Standard polar33892256
Cletoquine,2TBDMS,isomer #1CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C123255.1Semi standard non polar33892256
Cletoquine,2TBDMS,isomer #1CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C123127.0Standard non polar33892256
Cletoquine,2TBDMS,isomer #1CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C123510.3Standard polar33892256
Cletoquine,2TBDMS,isomer #2CC(CCCNCCO[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C3040.6Semi standard non polar33892256
Cletoquine,2TBDMS,isomer #2CC(CCCNCCO[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C3080.9Standard non polar33892256
Cletoquine,2TBDMS,isomer #2CC(CCCNCCO[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C3337.8Standard polar33892256
Cletoquine,2TBDMS,isomer #3CC(CCCN(CCO)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C3223.3Semi standard non polar33892256
Cletoquine,2TBDMS,isomer #3CC(CCCN(CCO)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C3137.9Standard non polar33892256
Cletoquine,2TBDMS,isomer #3CC(CCCN(CCO)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C3467.2Standard polar33892256
Cletoquine,3TBDMS,isomer #1CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C3424.0Semi standard non polar33892256
Cletoquine,3TBDMS,isomer #1CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C3276.5Standard non polar33892256
Cletoquine,3TBDMS,isomer #1CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C3337.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cletoquine GC-MS (Non-derivatized) - 70eV, Positivesplash10-055f-9150000000-7e101ec32b7d4d1187ab2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cletoquine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cletoquine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cletoquine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cletoquine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cletoquine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cletoquine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cletoquine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cletoquine 10V, Positive-QTOFsplash10-0a4j-0069000000-92dc6716d7cc2a9649e32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cletoquine 20V, Positive-QTOFsplash10-054k-0293000000-251909fdb91536548efd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cletoquine 40V, Positive-QTOFsplash10-004i-3950000000-ef9cf1c30f4b9a13a8512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cletoquine 10V, Negative-QTOFsplash10-0a4i-0019000000-270c91a68c9714bb91402021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cletoquine 20V, Negative-QTOFsplash10-0a4i-1279000000-73457ec28255e20325ad2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cletoquine 40V, Negative-QTOFsplash10-004i-3911000000-a584e5bc5f46c2e887d52021-10-12Wishart 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 ID64850
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71826
PDB IDNot Available
ChEBI IDNot Available
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 ]