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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:00:55 UTC
Update Date2019-07-23 07:15:08 UTC
HMDB IDHMDB0060810
Secondary Accession Numbers
  • HMDB60810
Metabolite Identification
Common Namecyclic 6-Hydroxymelatonin
Descriptioncyclic 6-Hydroxymelatonin belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. cyclic 6-Hydroxymelatonin is an extremely weak basic (essentially neutral) compound (based on its pKa). Melatonin Listen/ˌmɛləˈtoʊnɪn/, also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring compound found in animals, plants, and microbes. In animals, circulating levels of the hormone melatonin vary in a daily cycle, thereby allowing the entrainment of the circadian rhythms of several biological functions. cyclic 6-Hydroxymelatonin is a metabolite of melatonin.
Structure
Data?1563866108
SynonymsNot Available
Chemical FormulaC13H14N2O3
Average Molecular Weight246.2619
Monoisotopic Molecular Weight246.100442324
IUPAC Name1-{6-hydroxy-5-methoxy-1H,2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethan-1-one
Traditional Name1-{6-hydroxy-5-methoxy-2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethanone
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1O
InChI Identifier
InChI=1S/C13H14N2O3/c1-7(16)15-4-3-8-9-5-12(18-2)11(17)6-10(9)14-13(8)15/h5-6,14,17H,3-4H2,1-2H3
InChI KeyFQZIOEARFRBPDV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
Substituents
  • Pyrroloindole
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Acetamide
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Ether
  • Azacycle
  • Organonitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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
Water Solubility1.75 g/LALOGPS
logP1.27ALOGPS
logP0.84ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.56 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.13 m³·mol⁻¹ChemAxon
Polarizability26.21 ųChemAxon
Number of Rings3ChemAxon
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]+157.67531661259
DarkChem[M-H]-158.08931661259
DeepCCS[M+H]+156.47430932474
DeepCCS[M-H]-154.11630932474
DeepCCS[M-2H]-187.24330932474
DeepCCS[M+Na]+162.56830932474
AllCCS[M+H]+155.332859911
AllCCS[M+H-H2O]+151.532859911
AllCCS[M+NH4]+158.932859911
AllCCS[M+Na]+159.932859911
AllCCS[M-H]-160.232859911
AllCCS[M+Na-2H]-159.932859911
AllCCS[M+HCOO]-159.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cyclic 6-HydroxymelatoninCOC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1O3749.2Standard polar33892256
cyclic 6-HydroxymelatoninCOC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1O2500.1Standard non polar33892256
cyclic 6-HydroxymelatoninCOC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1O2618.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
cyclic 6-Hydroxymelatonin,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C1=C2CCN1C(C)=O2535.2Semi standard non polar33892256
cyclic 6-Hydroxymelatonin,1TMS,isomer #2COC1=CC2=C(C=C1O)N([Si](C)(C)C)C1=C2CCN1C(C)=O2536.1Semi standard non polar33892256
cyclic 6-Hydroxymelatonin,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C1=C2CCN1C(C)=O2562.4Semi standard non polar33892256
cyclic 6-Hydroxymelatonin,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C1=C2CCN1C(C)=O2408.9Standard non polar33892256
cyclic 6-Hydroxymelatonin,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C1=C2CCN1C(C)=O2827.3Standard polar33892256
cyclic 6-Hydroxymelatonin,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C1=C2CCN1C(C)=O2723.1Semi standard non polar33892256
cyclic 6-Hydroxymelatonin,1TBDMS,isomer #2COC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C1=C2CCN1C(C)=O2740.7Semi standard non polar33892256
cyclic 6-Hydroxymelatonin,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=C2CCN1C(C)=O2905.7Semi standard non polar33892256
cyclic 6-Hydroxymelatonin,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=C2CCN1C(C)=O2903.6Standard non polar33892256
cyclic 6-Hydroxymelatonin,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=C2CCN1C(C)=O3000.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cyclic 6-Hydroxymelatonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uec-2490000000-c8f196c332bb71882b9d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic 6-Hydroxymelatonin GC-MS (1 TMS) - 70eV, Positivesplash10-0hbd-3093000000-dce525816badc4bb10992017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic 6-Hydroxymelatonin 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 - cyclic 6-Hydroxymelatonin 10V, Positive-QTOFsplash10-0a4j-0090000000-a99ed1e16994593a509f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 20V, Positive-QTOFsplash10-0a4i-0390000000-bdcb012d7fe85e0008b52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 40V, Positive-QTOFsplash10-000i-0910000000-fed695acf0406f49ad1e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 10V, Negative-QTOFsplash10-0f6t-0090000000-167e69a93cce328c43012017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 20V, Negative-QTOFsplash10-0udr-0690000000-35d419421af3b77d21da2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 40V, Negative-QTOFsplash10-000i-0910000000-d5b76152c6440c325b902017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 10V, Negative-QTOFsplash10-0002-0090000000-b8d979fd88dcbd85fb572021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 20V, Negative-QTOFsplash10-0udr-0690000000-9873a1ba742bddd348352021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 40V, Negative-QTOFsplash10-0f79-0940000000-a1bbdda6f249aff64fa62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 10V, Positive-QTOFsplash10-0002-0090000000-4b96f2fb9c6435e349172021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 20V, Positive-QTOFsplash10-0002-0090000000-534cf3a7b9c5f3d9025e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 40V, Positive-QTOFsplash10-0uki-0930000000-fc7ca114e910a1f78f272021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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 IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769959
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 ReferencesNot Available