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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 00:03:56 UTC
Update Date2021-09-26 22:56:30 UTC
HMDB IDHMDB0247048
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-Chloromelatonin
Description6-CHLOROMELATONIN belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Based on a literature review a significant number of articles have been published on 6-CHLOROMELATONIN. This compound has been identified in human blood as reported by (PMID: 31557052 ). 6-chloromelatonin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 6-Chloromelatonin 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
SynonymsNot Available
Chemical FormulaC13H15ClN2O2
Average Molecular Weight266.73
Monoisotopic Molecular Weight266.0822054
IUPAC NameN-[2-(6-chloro-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Traditional NameN-[2-(6-chloro-5-methoxy-1H-indol-3-yl)ethyl]acetamide
CAS Registry NumberNot Available
SMILES
COC1=C(Cl)C=C2NC=C(CCNC(C)=O)C2=C1
InChI Identifier
InChI=1S/C13H15ClN2O2/c1-8(17)15-4-3-9-7-16-12-6-11(14)13(18-2)5-10(9)12/h5-7,16H,3-4H2,1-2H3,(H,15,17)
InChI KeyLUINDDOUWHRIPW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Anisole
  • Alkyl aryl ether
  • Aryl chloride
  • Aryl halide
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organohalogen compound
  • Organic oxygen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • 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
logP2.48ALOGPS
logP1.75ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.29ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.12 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.08 m³·mol⁻¹ChemAxon
Polarizability27.76 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]+159.86830932474
DeepCCS[M-H]-157.5130932474
DeepCCS[M-2H]-190.39630932474
DeepCCS[M+Na]+165.96130932474
AllCCS[M+H]+158.532859911
AllCCS[M+H-H2O]+154.932859911
AllCCS[M+NH4]+161.932859911
AllCCS[M+Na]+162.832859911
AllCCS[M-H]-162.032859911
AllCCS[M+Na-2H]-162.032859911
AllCCS[M+HCOO]-162.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-ChloromelatoninCOC1=C(Cl)C=C2NC=C(CCNC(C)=O)C2=C13548.0Standard polar33892256
6-ChloromelatoninCOC1=C(Cl)C=C2NC=C(CCNC(C)=O)C2=C12537.5Standard non polar33892256
6-ChloromelatoninCOC1=C(Cl)C=C2NC=C(CCNC(C)=O)C2=C12639.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Chloromelatonin,1TMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=C2CCNC(C)=O2625.4Semi standard non polar33892256
6-Chloromelatonin,1TMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=C2CCNC(C)=O2503.2Standard non polar33892256
6-Chloromelatonin,1TMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=C2CCNC(C)=O3074.8Standard polar33892256
6-Chloromelatonin,1TMS,isomer #2COC1=CC2=C(C=C1Cl)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C2526.4Semi standard non polar33892256
6-Chloromelatonin,1TMS,isomer #2COC1=CC2=C(C=C1Cl)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C2555.5Standard non polar33892256
6-Chloromelatonin,1TMS,isomer #2COC1=CC2=C(C=C1Cl)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C3094.6Standard polar33892256
6-Chloromelatonin,2TMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C2554.5Semi standard non polar33892256
6-Chloromelatonin,2TMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C2659.0Standard non polar33892256
6-Chloromelatonin,2TMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C2777.4Standard polar33892256
6-Chloromelatonin,1TBDMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=C2CCNC(C)=O2856.4Semi standard non polar33892256
6-Chloromelatonin,1TBDMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=C2CCNC(C)=O2675.8Standard non polar33892256
6-Chloromelatonin,1TBDMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=C2CCNC(C)=O3109.9Standard polar33892256
6-Chloromelatonin,1TBDMS,isomer #2COC1=CC2=C(C=C1Cl)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C2764.5Semi standard non polar33892256
6-Chloromelatonin,1TBDMS,isomer #2COC1=CC2=C(C=C1Cl)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C2751.5Standard non polar33892256
6-Chloromelatonin,1TBDMS,isomer #2COC1=CC2=C(C=C1Cl)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C3130.8Standard polar33892256
6-Chloromelatonin,2TBDMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C2993.3Semi standard non polar33892256
6-Chloromelatonin,2TBDMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C3028.2Standard non polar33892256
6-Chloromelatonin,2TBDMS,isomer #1COC1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C2937.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-Chloromelatonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9270000000-d287f5121ade3b50f2042021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Chloromelatonin 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 - 6-Chloromelatonin 10V, Positive-QTOFsplash10-0a4i-0090000000-583da85af48c9380ebed2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Chloromelatonin 20V, Positive-QTOFsplash10-0a4i-0090000000-0d208b4e0e1ee653b5902021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Chloromelatonin 40V, Positive-QTOFsplash10-05di-0910000000-c396dea35331efc6321a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Chloromelatonin 10V, Negative-QTOFsplash10-014i-0090000000-b8b04dcba5afdf28d9882021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Chloromelatonin 20V, Negative-QTOFsplash10-0a4i-9100000000-194d4a498645b711d1512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Chloromelatonin 40V, Negative-QTOFsplash10-001i-9400000000-cb55efaa38f741cc65082021-10-12Wishart 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 ID1790
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1858
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 ]