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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:32:46 UTC
HMDB IDHMDB15404
Secondary Accession NumbersNone
Metabolite Identification
Common NameDihydroergotoxine
DescriptionDihydroergotoxine is only found in individuals that have used or taken this drug. It is a cerebral vasodilator.Dihydroergotoxine is a mixture of three different ergotaman-3',6',18-triones, dihydroergocornine, dihydroergocristine, and dihydroergocryptine. It has been proposed to be a neuroprotective agent and a nootropic agent. The mechanism of its therapeutic actions is not clear, but it can act as an alpha-adrenergic antagonist and a dopamine agonist. Specifically it binds to the Dopamine D2 receptor and the GABAA receptor.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC34H41N5O8S
Average Molecular Weight679.783
Monoisotopic Molecular Weight679.267584003
IUPAC Name(4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-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),9,12,14-tetraene-4-carboxamide; methanesulfonic acid
Traditional Name(4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-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),9,12,14-tetraene-4-carboxamide; methanesulfonic acid
CAS Registry Number11032-41-0
SMILES
CS(O)(=O)=O.[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@@H]3CC4C5=C6C(C[C@@]4([H])N(C)C3)=CNC6=CC=C5)O[C@@]21O
InChI Identifier
InChI=1S/C33H37N5O5.CH4O3S/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32;1-5(2,3)4/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39);1H3,(H,2,3,4)/t21-,23?,25-,26+,27+,32-,33+;/m1./s1
InChI KeyInChIKey=ADYPXRFPBQGGAH-WVVAGBSPSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Dihydroergotamine
  • Hybrid peptide
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Quinoline-3-carboxamide
  • Pyrroloquinoline
  • N-acyl-alpha amino acid or derivatives
  • Quinoline
  • Piperidinecarboxylic acid
  • Piperidinecarboxamide
  • 3-piperidinecarboxamide
  • Isoindole or derivatives
  • Indole or derivatives
  • Indole
  • Aralkylamine
  • N-alkylpiperazine
  • Benzenoid
  • Piperidine
  • Piperazine
  • Oxazolidinone
  • 1,4-diazinane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Alkanesulfonic acid
  • Tertiary carboxylic acid amide
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Pyrrolidine
  • Pyrrole
  • Methanesulfonate
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Orthocarboxylic acid derivative
  • Lactam
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Alkanolamine
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
BiofunctionNot Available
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.71ChemAxon
pKa (Strongest Acidic)9.71ChemAxon
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.21 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity159.39 m3·mol-1ChemAxon
Polarizability61.93 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01287
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01287
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01287
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4925595
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB15404
Metagene LinkHMDB15404
METLIN IDNot Available
PubChem Compound6420006
PDB IDNot Available
ChEBI ID920559
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in glutamate-ammonia ligase activity
Specific function:
This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). Essential for proliferation of fetal skin fibroblasts.
Gene Name:
GLUL
Uniprot ID:
P15104
Molecular weight:
42064.15
References
  1. Pericic D: Effects of acute and subacute treatment with ergot drugs on the GABA system in specific brain regions. J Pharm Pharmacol. 1981 Oct;33(10):655-9. [6117619 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Markstein R: Hydergine: interaction with the neurotransmitter systems in the central nervous system. J Pharmacol. 1985;16 Suppl 3:1-17. [2869188 ]
  2. Korneyev AY, Cincotta AH: Identification of hepatic, non-monoamine, dihydroergocryptine binding sites with significant gender differences. Life Sci. 1996;58(12):241-8. [8786706 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Flynn BL, Ranno AE: Pharmacologic management of Alzheimer disease, Part II: Antioxidants, antihypertensives, and ergoloid derivatives. Ann Pharmacother. 1999 Feb;33(2):188-97. [10084415 ]
  2. Markstein R: Hydergine: interaction with the neurotransmitter systems in the central nervous system. J Pharmacol. 1985;16 Suppl 3:1-17. [2869188 ]
  3. Wadworth AN, Chrisp P: Co-dergocrine mesylate. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in age-related cognitive decline. Drugs Aging. 1992 May-Jun;2(3):153-73. [1606351 ]
  4. Korneyev AY, Cincotta AH: Identification of hepatic, non-monoamine, dihydroergocryptine binding sites with significant gender differences. Life Sci. 1996;58(12):241-8. [8786706 ]
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. Markstein R: Hydergine: interaction with the neurotransmitter systems in the central nervous system. J Pharmacol. 1985;16 Suppl 3:1-17. [2869188 ]
  2. Korneyev AY, Cincotta AH: Identification of hepatic, non-monoamine, dihydroergocryptine binding sites with significant gender differences. Life Sci. 1996;58(12):241-8. [8786706 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
References
  1. Tvrdeic A, Pericic D: Effect of ergot alkaloids on 3H-flunitrazepam binding to mouse brain GABAA receptors. Coll Antropol. 2003;27 Suppl 1:175-82. [12955907 ]
  2. Tvrdeic A, Pericic D: Dihydrogenated ergot compounds bind with high affinity to GABAA receptor-associated Cl- ionophore. Eur J Pharmacol. 1991 Sep 4;202(1):109-11. [1664802 ]
  3. Korneyev AY, Cincotta AH: Identification of hepatic, non-monoamine, dihydroergocryptine binding sites with significant gender differences. Life Sci. 1996;58(12):241-8. [8786706 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular weight:
49292.8
References
  1. Flynn BL, Ranno AE: Pharmacologic management of Alzheimer disease, Part II: Antioxidants, antihypertensives, and ergoloid derivatives. Ann Pharmacother. 1999 Feb;33(2):188-97. [10084415 ]
  2. Markstein R: Hydergine: interaction with the neurotransmitter systems in the central nervous system. J Pharmacol. 1985;16 Suppl 3:1-17. [2869188 ]
  3. Wadworth AN, Chrisp P: Co-dergocrine mesylate. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in age-related cognitive decline. Drugs Aging. 1992 May-Jun;2(3):153-73. [1606351 ]
  4. Korneyev AY, Cincotta AH: Identification of hepatic, non-monoamine, dihydroergocryptine binding sites with significant gender differences. Life Sci. 1996;58(12):241-8. [8786706 ]