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Record Information
Version3.6
Creation Date2013-07-04 18:59:04 UTC
Update Date2016-02-11 08:12:48 UTC
HMDB IDHMDB60782
Secondary Accession NumbersNone
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=1/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-/s2
InChI KeyInChIKey=YAICYXFUKKMAKO-PSWSUSLKNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentLysergic acids
Alternative Parents
Substituents
  • Lysergic acid
  • Indoloquinoline
  • Benzoquinoline
  • Quinoline-3-carboxylic acid
  • Pyrroloquinoline
  • Quinoline
  • Piperidinecarboxylic acid
  • Isoindole or derivatives
  • Indole or derivatives
  • Indole
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity86.01 m3·mol-1ChemAxon
Polarizability33.2 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB60782
Metagene LinkHMDB60782
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