Ergocristine (CHEM002657)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (7)XML
Record Information
Version1.0
Creation Date2010-04-23 19:56:58 UTC
Update Date2026-03-27 01:57:06 UTC
Accession NumberCHEM002657
Identification
Common NameErgocristine
ClassSmall Molecule
DescriptionErgocristine is an alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. Ergocristine is one of 3 similar peptides referred to as ergotoxine alkaloids, the other two being ergocryptine and ergocornine. Ergotoxines prepared into their hihydroergotoxine mesylates, commonly known as ergoloid mesylates, are used in the symptomatic therapy of age-related dementia. Long term exposure to some ergoline alkaloids can cause ergotism, a disease causing convulsive and gangrenous symptoms. (6, 3)
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC35H39N5O5
Average Molecular Mass609.715 g/mol
Monoisotopic Mass609.295 g/mol
CAS Registry Number511-08-0
IUPAC NameN-[7-benzyl-2-hydroxy-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
Traditional NameN-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
SMILESCC(C)C1(NC(=O)C2CN(C)C3CC4=CNC5=CC=CC(=C45)C3=C2)OC2(O)C3CCCN3C(=O)C(CC3=CC=CC=C3)N2C1=O
InChI IdentifierInChI=1S/C35H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41)
InChI KeyHEFIYUQVAZFDEE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ergotamines, dihydroergotamines, and derivatives. These are organic compounds containing an ergotamine moiety, which is structurally characterized by a benzyl substituent attached to the piperazine ring of the ergopeptine backbone.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentErgotamines, dihydroergotamines, and derivatives
Alternative Parents
Substituents
  • Ergotamine
  • Hybrid peptide
  • Alpha-dipeptide
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Quinoline-3-carboxamide
  • N-acyl-alpha amino acid or derivatives
  • Pyrroloquinoline
  • Quinoline
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Aralkylamine
  • N-alkylpiperazine
  • Monocyclic benzene moiety
  • 1,4-diazinane
  • Benzenoid
  • Oxazolidinone
  • Piperazine
  • Pyrrole
  • Pyrrolidine
  • Heteroaromatic compound
  • Oxazolidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Tertiary amine
  • Amino acid or derivatives
  • Lactam
  • Tertiary aliphatic amine
  • Secondary carboxylic acid amide
  • Orthocarboxylic acid derivative
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alkanolamine
  • Oxacycle
  • Azacycle
  • Organooxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP3.6ALOGPS
logP3.71ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.7ChemAxon
pKa (Strongest Basic)7.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.21 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity169.05 m³·mol⁻¹ChemAxon
Polarizability64.2 ųChemAxon
Number of Rings8ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0adi-0089000000-aeb1e8528313eebff9d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-05fr-0192000000-6a63208107ddccf9b39dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0013093000-1b0fea51c7fe0dedfde9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000039000-c69211be46cc2870d7bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-05fr-0390000000-e1f07783820b230966fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0013093000-608600897b7d5682d5f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0adi-0089000000-9f03a24b346c4a0525f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-05fr-0390000000-c889004b1cbb17a2939bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0012029000-9a018cf7b722914999a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfu-3092021000-0a198fcee08b7c28091dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-6291000000-37a1ed4ec31119a247d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-0029024000-98afdccc16056646ad0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-3279061000-aebfaeae22d86e744678Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0g4i-9730000000-37e2f6daf69bab611e50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-d646e0db5d212a9b1f86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0084049000-93ad6ca9490700177497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0090020000-64570a453017341fe142Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000009000-21c3927cf13f38eaf54fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0066029000-1052a1acaceff9c662e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-2192001000-a805021c248fab52d515Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (5)
Mechanism of ToxicityErgoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Ergometrine is also known to have a non-receptor specific oxytocic activity. (2, 3, 4)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesErgocristine is an alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. Ergocristine is one of 3 similar peptides referred to as ergotoxine alkaloids, the other two being ergocryptine and ergocornine. Ergotoxines prepared into their hihydroergotoxine mesylates, commonly known as ergoloid mesylates, are used in the symptomatic therapy of age-related dementia. (6, 3)
Minimum Risk LevelNot Available
Health EffectsIngestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (1)
SymptomsConvulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (7)
TreatmentTreatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (8)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0251908
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkErgocristine
Chemspider ID88725
ChEBI IDNot Available
PubChem Compound ID98255
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.