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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:15:56 UTC
HMDB IDHMDB0014837
Secondary Accession Numbers
  • HMDB14837
Metabolite Identification
Common NameNicergoline
DescriptionNicergoline is only found in individuals that have used or taken this drug. It is an 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. [PubChem]Nicergoline acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation. Therefore the mechanism of Nicergoline is to increase vascular circulation in the brain, thereby enhancing the transmission of nerve signals across the nerve fibres, which secrete acetylcholine as a neural transmitter.
Structure
Data?1582753225
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 Weight484.386
Monoisotopic Molecular Weight483.11575436
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
CAS Registry Number27848-84-6
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 Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 g/LNot Available
LogP3.3Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M+H]+Not Available213.815http://allccs.zhulab.cn/database/detail?ID=AllCCS00001017
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP10(3.99) g/LALOGPS
logP10(3.7) g/LChemAxon
logS10(-4.6) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nicergoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-01oy-0490000000-9946900f54448caef05c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nicergoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nicergoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 10V, Positive-QTOFsplash10-001i-0070900000-31a0fe890dfcef178a8d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 20V, Positive-QTOFsplash10-001i-0090200000-e7257eb7542660c9b4c72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 40V, Positive-QTOFsplash10-0pc0-2390000000-90dd1884dd9a2c36f4522016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 10V, Negative-QTOFsplash10-001i-0110900000-1589cacb0deaf83631312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 20V, Negative-QTOFsplash10-0532-0920500000-513d6a319962dbf7cbf32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 40V, Negative-QTOFsplash10-0a4j-0920000000-330babe951e9ccb2384a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 10V, Positive-QTOFsplash10-0udi-0000900000-2649cd14eb52b3a4655b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 20V, Positive-QTOFsplash10-001i-0000900000-a0efe44d5c8b6301ef532021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 40V, Positive-QTOFsplash10-0udi-0391000000-906dc143d70f8ce61d0e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 10V, Negative-QTOFsplash10-001i-0000900000-b7c2f66e57ef37412e1a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 20V, Negative-QTOFsplash10-003r-4100900000-fe5f17d8fb6e1a206cbd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicergoline 40V, Negative-QTOFsplash10-0a6r-2900100000-a189dad93ea9944c264f2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00699 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00699 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00699
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID31373
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNicergoline
METLIN IDNot Available
PubChem Compound34040
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:18666801 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Alvarez-Guerra M, Bertholom N, Garay RP: Selective blockade by nicergoline of vascular responses elicited by stimulation of alpha 1A-adrenoceptor subtype in the rat. Fundam Clin Pharmacol. 1999;13(1):50-8. [PubMed:10027088 ]