Nicergoline (CHEM018435)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:15:16 UTC
Update Date2016-11-09 01:15:48 UTC
Accession NumberCHEM018435
Identification
Common NameNicergoline
ClassSmall Molecule
DescriptionAn ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It has been suggested to ameliorate cognitive deficits in cerebrovascular disease.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SermionKegg
Circo-marenHMDB
Dexcel brand OF nicergolineHMDB
Nicergolin atidHMDB
Nicergolin lindoHMDB
Nicergolin-neuraxpharmHMDB
Nicergoline hexal brandHMDB
NiceriumHMDB
NicotergolineHMDB
Pfizer brand OF nicergolineHMDB
Teva brand OF nicergolineHMDB
CT Arzneimittel brand OF nicergolineHMDB
Neuraxpharm brand OF nicergolineHMDB
Ratiopharm brand OF nicergolineHMDB
Circo marenHMDB
FisifaxHMDB
Hormosan brand OF nicergolineHMDB
NicergobetaHMDB
Nicergolin neuraxpharmHMDB
Nicergolin-ratiopharmHMDB
Nicergoline pfizer brandHMDB
Nicergoline teva brandHMDB
Reig jofre brand OF nicergolineHMDB
Aventis brand OF nicergolineHMDB
F.I. 6714HMDB
Hexal brand OF nicergolineHMDB
Lindopharm brand OF nicergolineHMDB
Nicergolin-tevaHMDB
Betapharm brand OF nicergolineHMDB
Kenfarma brand OF nicergolineHMDB
Krewel brand OF nicergolineHMDB
Nicergolin tevaHMDB
Nicergolin ratiopharmHMDB
NimergolineHMDB
CT-Arzneimittel brand OF nicergolineHMDB
ErgobelHMDB
Nicergolin von CTHMDB
Von CT, nicergolinHMDB
Chemical FormulaC24H26BrN3O3
Average Molecular Mass484.386 g/mol
Monoisotopic Mass483.116 g/mol
CAS Registry Number27848-84-6
IUPAC Name[(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate
Traditional Namenicergoline
SMILES[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@]1(C[C@@H](COC(=O)C1=CC(Br)=CN=C1)CN2C)OC
InChI IdentifierInChI=1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1
InChI KeyYSEXMKHXIOCEJA-FVFQAYNVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassIndoloquinolines
Direct ParentIndoloquinolines
Alternative Parents
Substituents
  • Ergoline skeleton
  • Indoloquinoline
  • Benzoquinoline
  • Pyrroloquinoline
  • N-alkylindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Pyridine carboxylic acid
  • Alkaloid or derivatives
  • Pyridine carboxylic acid or derivatives
  • Aralkylamine
  • Aryl bromide
  • Aryl halide
  • N-methylpyrrole
  • Piperidine
  • Benzenoid
  • Pyridine
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Dialkyl ether
  • Ether
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organic nitrogen compound
  • Organobromide
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3.99ALOGPS
logP3.7ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)8.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area56.59 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.3 m³·mol⁻¹ChemAxon
Polarizability48.08 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01oy-0490000000-9946900f54448caef05cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0070900000-31a0fe890dfcef178a8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0090200000-e7257eb7542660c9b4c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc0-2390000000-90dd1884dd9a2c36f452Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0110900000-1589cacb0deaf8363131Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0920500000-513d6a319962dbf7cbf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-0920000000-330babe951e9ccb2384aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-2649cd14eb52b3a4655bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000900000-a0efe44d5c8b6301ef53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0391000000-906dc143d70f8ce61d0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-b7c2f66e57ef37412e1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4100900000-fe5f17d8fb6e1a206cbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-2900100000-a189dad93ea9944c264fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00699
HMDB IDHMDB0014837
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNicergoline
Chemspider ID31373
ChEBI IDNot Available
PubChem Compound ID34040
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52.