Ergovaline
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Basic Info
| Common Name | Ergovaline(F04938) |
| 2D Structure | |
| Description | Ergovaline is an ergopeptine and 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. Long term exposure to some ergoline alkaloids can cause ergotism, a disease causing convulsive and gangrenous symptoms. (L1918) |
| FRCD ID | F04938 |
| CAS Number | 2873-38-3 |
| PubChem CID | 104843 |
| Formula | C29H35N5O5 |
| IUPAC Name | None |
| InChI Key | BGHDUTQZGWOQIA-VQSKNWBGSA-N |
| InChI | InChI=1S/C29H35N5O5/c1-15(2)24-26(36)33-10-6-9-22(33)29(38)34(24)27(37)28(3,39-29)31-25(35)17-11-19-18-7-5-8-20-23(18)16(13-30-20)12-21(19)32(4)14-17/h5,7-8,11,13,15,17,21-22,24,30,38H,6,9-10,12,14H2,1-4H3,(H,31,35)/t17-,21-,22+,24+,28-,29+/m1/s1 |
| Canonical SMILES | CC(C)C1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C)NC(=O)C4CN(C5CC6=CNC7=CC=CC(=C67)C5=C4)C)O |
| Isomeric SMILES | CC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)O |
| Wikipedia | Ergovaline |
| Synonyms |
UNII-059E2O9IV4
12'-Hydroxy-2'-methyl-5'alpha-(1-methylethyl)-ergotaman-3',6',18-trione
Ergovaline
2873-38-3
059E2O9IV4
C29H35N5O5
Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylethyl)-, (5'alpha)-
AC1L2XLN
SCHEMBL14887086
ZINC95803330
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Alkaloids and derivatives |
| Class | Ergoline and derivatives |
| Subclass | Lysergic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Ergopeptines |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Hybrid peptide - Ergopeptine - 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 - 1,4-diazinane - Benzenoid - Oxazolidinone - Piperazine - Pyrrolidine - Pyrrole - Heteroaromatic compound - Tertiary carboxylic acid amide - Oxazolidine - Carboxamide group - Amino acid or derivatives - Lactam - Tertiary aliphatic amine - Tertiary amine - Orthocarboxylic acid derivative - Secondary carboxylic acid amide - Organoheterocyclic compound - Carboxylic acid derivative - Oxacycle - Azacycle - Alkanolamine - Amine - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as ergopeptines. These are ergoline derivatives that contain a tripeptide structure attached to the basic ergoline ring in the same location as the amide group of the lysergic acid derivatives. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 533.629 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 3 |
| Complexity | 1130 |
| Monoisotopic Mass | 533.264 |
| Exact Mass | 533.264 |
| XLogP | 1.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 39 |
| Defined Atom Stereocenter Count | 6 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9839 |
| Human Intestinal Absorption | HIA+ | 0.9602 |
| Caco-2 Permeability | Caco2- | 0.7378 |
| P-glycoprotein Substrate | Substrate | 0.8843 |
| P-glycoprotein Inhibitor | Inhibitor | 0.8469 |
| Inhibitor | 0.5143 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8699 |
| Distribution | ||
| Subcellular localization | Nucleus | 0.3809 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7955 |
| CYP450 2D6 Substrate | Non-substrate | 0.8921 |
| CYP450 3A4 Substrate | Substrate | 0.7756 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9107 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9182 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9236 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5493 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7960 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7734 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9554 |
| Non-inhibitor | 0.6801 | |
| AMES Toxicity | Non AMES toxic | 0.8593 |
| Carcinogens | Non-carcinogens | 0.9513 |
| Fish Toxicity | High FHMT | 0.9944 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8970 |
| Honey Bee Toxicity | Low HBT | 0.5842 |
| Biodegradation | Not ready biodegradable | 0.9567 |
| Acute Oral Toxicity | III | 0.5849 |
| Carcinogenicity (Three-class) | Non-required | 0.5098 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7400 | LogS |
| Caco-2 Permeability | 0.5900 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.9613 | LD50, mol/kg |
| Fish Toxicity | 1.1135 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4965 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Forms of selenium in vitamin-mineral mixes differentially affect serum prolactin concentration and hepatic glutamine synthetase activity of steers grazing endophyte-infected tall fescue. | J Anim Sci | 2018 Mar 6 | 29385471 |
| Ergovaline does not alter the severity of ryegrass staggers induced by lolitrem B. | N Z Vet J | 2018 Mar | 29241023 |
| Effects of grazing different ergovaline concentrations on vasoactivity of bovine lateral saphenous vein. | J Anim Sci | 2018 Jun 29 | 29701794 |
| Co-exposure of the Mycotoxins Lolitrem B and Ergovaline in Steers Fed Perennial Ryegrass ( Lolium perenne) Straw: Metabolic Characterization of Excreta. | J Agric Food Chem | 2018 Jun 27 | 29847929 |
| Development and validation of an ultrahigh performance liquid chromatography-high resolution tandem mass spectrometry assay for nine toxic alkaloids from endophyte-infected pasture grasses in horse serum. | J Chromatogr A | 2018 Jul 27 | 29779692 |
| Immunochemical Analysis of Paxilline and Ergot Alkaloid Mycotoxins in Grass Seeds and Plants. | J Agric Food Chem | 2018 Jan 10 | 29237259 |
| Vasoactivity and Vasoconstriction Changes in Cattle Related to Time off Toxic Endophyte-Infected Tall Fescue. | Toxins (Basel) | 2016 Sep 22 | 27669299 |
| Lolitrem B and Indole Diterpene Alkaloids Produced by Endophytic Fungi of the Genus Epichloë and Their Toxic Effects in Livestock. | Toxins (Basel) | 2016 Feb 15 | 26891327 |
| Chromosome-End Knockoff Strategy to Reshape Alkaloid Profiles of a Fungal Endophyte. | G3 (Bethesda) | 2016 Aug 9 | 27334939 |
| Ergot alkaloids produced by endophytic fungi of the genus Epichloë. | Toxins (Basel) | 2015 Mar 6 | 25756954 |
| Toxicity of endophyte-infected ryegrass hay containing high ergovaline level in lactating ewes. | J Anim Sci | 2015 Aug | 26440189 |
| The role of the Oregon State University Endophyte Service Laboratory in diagnosing clinical cases of endophyte toxicoses. | J Agric Food Chem | 2014 Jul 30 | 25017309 |
| Ergovaline and lolitrem B concentrations in perennial ryegrass in field culture in southern France: distribution in the plant and impact of climatic factors. | J Agric Food Chem | 2014 Dec 31 | 25526521 |
| Dietary exposure to ergot alkaloids decreases contractility of bovine mesenteric vasculature. | J Anim Sci | 2014 Apr | 24492572 |
| Combined effects of fungal alkaloids on intestinal motility in an in vitro rat model. | J Anim Sci | 2013 Nov | 23989880 |
| Preference for tannin-containing supplements by sheep consumingendophyte-infected tall fescue hay. | J Anim Sci | 2013 Jul | 23658337 |
| Effects of fescue toxicosis on bull growth, semen characteristics, and breeding soundness evaluation. | J Anim Sci | 2013 Aug | 23739791 |
| Use of different levels of ground endophyte-infected tall fescue seed during heat stress to separate characteristics of fescue toxicosis. | J Anim Sci | 2012 Oct | 23038746 |
| Constriction of bovine vasculature caused by endophyte-infected tall fescue seed extract is similar to pure ergovaline. | J Anim Sci | 2012 May | 22147482 |
| Clinical expression of lolitrem B (perennial ryegrass) intoxication in horses. | Equine Vet J | 2012 May | 21793878 |
Targets
- General Function:
- Potassium channel regulator activity
- Specific Function:
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name:
- DRD2
- Uniprot ID:
- P14416
- Molecular Weight:
- 50618.91 Da
- Mechanism of Action:
- Ergovalie acts as an agonist at the D2 dopamine receptor, creating second messenger responses similar to that of dopamine and inhibiting cyclic AMP production.
References
- Larson BT, Harmon DL, Piper EL, Griffis LM, Bush LP: Alkaloid binding and activation of D2 dopamine receptors in cell culture. J Anim Sci. 1999 Apr;77(4):942-7. [10328360 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity. Regulates the release of 5-hydroxytryptamine in the brain, and thereby affects neural activity. May also play a role in regulating the release of other neurotransmitters. May play a role in vasoconstriction.
- Gene Name:
- HTR1D
- Uniprot ID:
- P28221
- Molecular Weight:
- 41906.38 Da
- Mechanism of Action:
- Ergovalie acts as an agonist at vascular 5-HT1D receptors, causing the constriction of blood vessels.
References
- Schoning C, Flieger M, Pertz HH: Complex interaction of ergovaline with 5-HT2A, 5-HT1B/1D, and alpha1 receptors in isolated arteries of rat and guinea pig. J Anim Sci. 2001 Aug;79(8):2202-9. [11518230 ]
- General Function:
- Protein heterodimerization activity
- 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. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
- Gene Name:
- ADRA1A
- Uniprot ID:
- P35348
- Molecular Weight:
- 51486.005 Da
- Mechanism of Action:
- Ergovalie acts as a partial agonist at alpha-1 adrenoreceptors, inhibiting the contractile response to norepinephrine.
References
- Schoning C, Flieger M, Pertz HH: Complex interaction of ergovaline with 5-HT2A, 5-HT1B/1D, and alpha1 receptors in isolated arteries of rat and guinea pig. J Anim Sci. 2001 Aug;79(8):2202-9. [11518230 ]
- General Function:
- Protein heterodimerization activity
- 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. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
- Gene Name:
- ADRA1B
- Uniprot ID:
- P35368
- Molecular Weight:
- 56835.375 Da
- Mechanism of Action:
- Ergovalie acts as a partial agonist at alpha-1 adrenoreceptors, inhibiting the contractile response to norepinephrine.
References
- Schoning C, Flieger M, Pertz HH: Complex interaction of ergovaline with 5-HT2A, 5-HT1B/1D, and alpha1 receptors in isolated arteries of rat and guinea pig. J Anim Sci. 2001 Aug;79(8):2202-9. [11518230 ]
- General Function:
- Alpha1-adrenergic receptor activity
- Specific Function:
- This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
- Gene Name:
- ADRA1D
- Uniprot ID:
- P25100
- Molecular Weight:
- 60462.205 Da
- Mechanism of Action:
- Ergovalie acts as a partial agonist at alpha-1 adrenoreceptors, inhibiting the contractile response to norepinephrine.
References
- Schoning C, Flieger M, Pertz HH: Complex interaction of ergovaline with 5-HT2A, 5-HT1B/1D, and alpha1 receptors in isolated arteries of rat and guinea pig. J Anim Sci. 2001 Aug;79(8):2202-9. [11518230 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances, such as lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity. Arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Regulates the release of 5-hydroxytryptamine, dopamine and acetylcholine in the brain, and thereby affects neural activity, nociceptive processing, pain perception, mood and behavior. Besides, plays a role in vasoconstriction of cerebral arteries.
- Gene Name:
- HTR1B
- Uniprot ID:
- P28222
- Molecular Weight:
- 43567.535 Da
- Mechanism of Action:
- Ergovalie acts as an agonist at vascular 5-HT1B receptors, causing the constriction of blood vessels.
References
- Schoning C, Flieger M, Pertz HH: Complex interaction of ergovaline with 5-HT2A, 5-HT1B/1D, and alpha1 receptors in isolated arteries of rat and guinea pig. J Anim Sci. 2001 Aug;79(8):2202-9. [11518230 ]
- General Function:
- Virus receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction.(Microbial infection) Acts as a receptor for human JC polyomavirus/JCPyV.
- Gene Name:
- HTR2A
- Uniprot ID:
- P28223
- Molecular Weight:
- 52602.58 Da
- Mechanism of Action:
- Ergovalie acts as an agonist at vascular 5-HT2A receptors, causing the constriction of blood vessels.
References
- Schoning C, Flieger M, Pertz HH: Complex interaction of ergovaline with 5-HT2A, 5-HT1B/1D, and alpha1 receptors in isolated arteries of rat and guinea pig. J Anim Sci. 2001 Aug;79(8):2202-9. [11518230 ]