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Record Information
Version4.0
Creation Date2013-07-04 18:59:04 UTC
Update Date2017-09-27 08:43:54 UTC
HMDB IDHMDB0060782
Secondary Accession Numbers
  • HMDB60782
Metabolite Identification
Common Name6-allyl-8b-Carboxy-ergoline
Description6-allyl-8b-Carboxy-ergoline is a metabolite of cabergoline. Cabergoline (brand names Dostinex and Cabaser), an ergot derivative, is a potent dopamine receptor agonist on D2 receptors. In vitro, rat studies show cabergoline has a direct inhibitory effect on pituitary lactotroph cells. It is frequently used as a first-line agent in the management of prolactinomas due to higher affinity for D2 receptor sites, less severe side effects, and more convenient dosing schedule than the older bromocriptine. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H20N2O2
Average Molecular Weight296.3636
Monoisotopic Molecular Weight296.152477894
IUPAC Name(2S,7S)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxylic acid
Traditional Name(2S,7S)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1C[C@@H]2[C@H](CC3=CNC4=CC=CC2=C34)N(CC=C)C1
InChI Identifier
InChI=1S/C18H20N2O2/c1-2-6-20-10-12(18(21)22)7-14-13-4-3-5-15-17(13)11(9-19-15)8-16(14)20/h2-5,9,12,14,16,19H,1,6-8,10H2,(H,21,22)/t12?,14-,16-/m0/s1
InChI KeyYAICYXFUKKMAKO-DBQWNMKUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as lysergic acids. These are derivatives of lysergic acid are amides in which the amidic moiety is formed by a small peptide or an alkylamide.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassErgoline and derivatives
Direct ParentLysergic acids
Alternative Parents
Substituents
  • Lysergic acid
  • Indoloquinoline
  • Benzoquinoline
  • Pyrroloquinoline
  • Quinoline-3-carboxylic acid
  • 3-alkylindole
  • Quinoline
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Piperidinecarboxylic acid
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen 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 Solubility0.31 g/LALOGPS
logP2.7ALOGPS
logP0.13ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
pKa (Strongest Basic)8.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area56.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity86.01 m³·mol⁻¹ChemAxon
Polarizability33.2 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, Positivesplash10-0g4j-2980000000-76cae1d8424dfce15becView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9562000000-65ab2a718e6b497d43a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0090000000-9a9af1b285c8c480ada4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-3090000000-8ffb90c1d1c03f32eacfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9540000000-375d1aa87f5ac4c528bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-cd483a3ffe2e812ad8a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-237c8a3695e0fe5c6d9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-1290000000-4ba40ff493211410f53cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00757
      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