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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:52:18 UTC
Update Date2019-07-23 07:13:32 UTC
HMDB IDHMDB0060069
Secondary Accession Numbers
  • HMDB60069
Metabolite Identification
Common Namecyclic 3-Hydroxymelatonin
Descriptioncyclic 3-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 3-Hydroxymelatonin is a moderately basic compound (based on its pKa).
Structure
Data?1563866012
SynonymsNot Available
Chemical FormulaC13H16N2O3
Average Molecular Weight248.2777
Monoisotopic Molecular Weight248.116092388
IUPAC Name1-{3a-hydroxy-5-methoxy-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-1-yl}ethan-1-one
Traditional Name1-{3a-hydroxy-5-methoxy-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-1-yl}ethanone
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(NC3N(CCC23O)C(C)=O)C=C1
InChI Identifier
InChI=1S/C13H16N2O3/c1-8(16)15-6-5-13(17)10-7-9(18-2)3-4-11(10)14-12(13)15/h3-4,7,12,14,17H,5-6H2,1-2H3
InChI KeyVADOSKJWFKUPQF-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
  • Indole
  • Dihydroindole
  • Anisole
  • N-acylpyrrolidine
  • Alkyl aryl ether
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Pyrrole
  • Pyrrolidine
  • Acetamide
  • Tertiary alcohol
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary amine
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.5 g/LALOGPS
logP0.67ALOGPS
logP-0.21ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)13ChemAxon
pKa (Strongest Basic)1.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.8 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.05 m³·mol⁻¹ChemAxon
Polarizability25.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1920000000-d9480054221e25bb27e8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-4191000000-cc7a5237ee02233fa4a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-0090000000-7c7286c5d8bfe91b2751Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0690000000-e6bb77b8c9434f4ce36aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-1900000000-49cd1cd77abdb506c358Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0090000000-33a11534cefc1d89b070Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0980000000-8195567db4a7a8ff6da6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052s-3910000000-0c90de6b946e8d2b674eSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 Compound85950298
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]