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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:11:33 UTC
Update Date2017-12-07 18:37:18 UTC
HMDB IDHMDB0060995
Secondary Accession Numbers
  • HMDB60995
Metabolite Identification
Common Name10-alpha-methoxy-9,10-dihydrolysergol
Description10-alpha-methoxy-9,10-dihydrolysergol is a metabolite of nicergoline. Nicergoline (marketed under the trade name Sermion) is an ergot derivative used to treat senile dementia and other disorders with vascular origins. It has been found to increase mental agility and enhance clarity and perception. It decreases vascular resistance and increases arterial blood flow in the brain, improving the utilization of oxygen and glucose by brain cells. It has similar vasoactive properties in other areas of the body, particularly the lungs. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H22N2O2
Average Molecular Weight286.3688
Monoisotopic Molecular Weight286.168127958
IUPAC Name[(4R)-2-methoxy-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol
Traditional Name[(4R)-2-methoxy-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol
CAS Registry NumberNot Available
SMILES
COC12C[C@@H](CO)CN(C)C1CC1=CNC3=CC=CC2=C13
InChI Identifier
InChI=1S/C17H22N2O2/c1-19-9-11(10-20)7-17(21-2)13-4-3-5-14-16(13)12(8-18-14)6-15(17)19/h3-5,8,11,15,18,20H,6-7,9-10H2,1-2H3/t11-,15?,17?/m1/s1
InChI KeyJGQZSBLQHCTAJF-NFXPUDJFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassErgoline and derivatives
Direct ParentClavines and derivatives
Alternative Parents
Substituents
  • Clavine skeleton
  • Indoloquinoline
  • Benzoquinoline
  • Pyrroloquinoline
  • Quinoline
  • 3-alkylindole
  • Isoindole or derivatives
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • 1,3-aminoalcohol
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary amine
  • Tertiary aliphatic amine
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility0.89 g/LALOGPS
logP2.15ALOGPS
logP1.43ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)15.41ChemAxon
pKa (Strongest Basic)8.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.49 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity83.11 m³·mol⁻¹ChemAxon
Polarizability32.2 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004s-1950000000-d8367098f8214f599e0aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-005a-3961000000-b461d735b6724f466171View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0090000000-717fd2849930b4428a64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0090000000-4510b13bf0fa192a4142View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9270000000-979a002d5a3a0c2c2cadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-46330b9fd6abedc135a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0090000000-423065c9eabcd800e842View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001c-8590000000-c98f52224a3d98e1df0fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00320
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB 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 CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available