Agroclavine
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Basic Info
| Common Name | Agroclavine(F04939) |
| 2D Structure | |
| Description | Agroclavine is a naturally occuring alkaloid of the ergoline family. As it is derived from dimethylergoline, it is referred to as a clavine. 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 | F04939 |
| CAS Number | 548-42-5 |
| PubChem CID | 73484 |
| Formula | C16H18N2 |
| IUPAC Name | (6aR,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline |
| InChI Key | XJOOMMHNYOJWCZ-UKRRQHHQSA-N |
| InChI | InChI=1S/C16H18N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,13,15,17H,7,9H2,1-2H3/t13-,15-/m1/s1 |
| Canonical SMILES | CC1=CC2C(CC3=CNC4=CC=CC2=C34)N(C1)C |
| Isomeric SMILES | CC1=C[C@H]2[C@@H](CC3=CNC4=CC=CC2=C34)N(C1)C |
| Synonyms |
Agroclavine
8,9-Didehydro-6,8-dimethylergoline
548-42-5
UNII-A8SW57GO7T
(-)-agroclavine
CCRIS 2099
Ergoline, 8,9-didehydro-6,8-dimethyl-
(5R,10R)-agroclavine
EINECS 208-947-3
6,8-Dimethyl-8,9-didehydroergoline
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Alkaloids and derivatives |
| Class | Ergoline and derivatives |
| Subclass | Clavines and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Clavines and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Clavine skeleton - Benzoquinoline - Pyrroloquinoline - Quinoline - 3-alkylindole - Indole - Indole or derivatives - Isoindole or derivatives - Aralkylamine - Benzenoid - Pyrrole - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Organoheterocyclic compound - Azacycle - Amine - Organonitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 238.334 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 375 |
| Monoisotopic Mass | 238.147 |
| Exact Mass | 238.147 |
| XLogP | 2.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 18 |
| Defined Atom Stereocenter Count | 2 |
| 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+ | 0.9880 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.6005 |
| P-glycoprotein Substrate | Substrate | 0.7987 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.5637 |
| Non-inhibitor | 0.7360 | |
| Renal Organic Cation Transporter | Inhibitor | 0.7205 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.3652 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8476 |
| CYP450 2D6 Substrate | Non-substrate | 0.7165 |
| CYP450 3A4 Substrate | Substrate | 0.6389 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9106 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9070 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8932 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7199 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6509 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8505 |
| Non-inhibitor | 0.6231 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.9648 |
| Fish Toxicity | High FHMT | 0.9167 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9453 |
| Honey Bee Toxicity | Low HBT | 0.6309 |
| Biodegradation | Not ready biodegradable | 0.9654 |
| Acute Oral Toxicity | II | 0.5650 |
| Carcinogenicity (Three-class) | Non-required | 0.7263 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.4670 | LogS |
| Caco-2 Permeability | 1.3489 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.9400 | LD50, mol/kg |
| Fish Toxicity | 0.7244 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4722 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Optimized QuEChERS Method Combined with UHPLC-MS/MS for the Simultaneous Determination of 15 Mycotoxins in Liquorice. | J AOAC Int | 2018 May 1 | 29073944 |
| Review on Mycotoxin Issues in Ruminants: Occurrence in Forages, Effects of Mycotoxin Ingestion on Health Status and Animal Performance and Practical Strategies to Counteract Their Negative Effects. | Toxins (Basel) | 2015 Aug 12 | 26274974 |
| Cooccurrence of mycotoxins in maize and poultry feeds from Brazil by liquid chromatography/tandem mass spectrometry. | ScientificWorldJournal | 2013 | 24348157 |
| Single-kernel analysis of fumonisins and other fungal metabolites in maize from South African subsistence farmers. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2011 Dec | 22023397 |
| Indole-diterpenes and ergot alkaloids in Cynodon dactylon (Bermuda grass) infected with Claviceps cynodontis from an outbreak of tremors in cattle. | J Agric Food Chem | 2009 Dec 9 | 19891432 |
| Mycotoxins and other secondary metabolites produced in vitro by Penicillium paneum Frisvad and Penicillium roqueforti Thom isolated from baled grass silage in Ireland. | J Agric Food Chem | 2006 Nov 29 | 17117820 |
| Analysis of endophyte toxins: fescue and other grasses toxic to livestock. | J Anim Sci | 1995 Mar | 7608022 |
Targets
- General Function:
- G-protein coupled amine receptor activity
- Specific Function:
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
- Gene Name:
- DRD5
- Uniprot ID:
- P21918
- Molecular Weight:
- 52950.5 Da
- Mechanism of Action:
- Agroclavin has agonistic activity at the D1 dopamine receptors, causing increases in cyclic AMP levels, increases in NK (natural killer) cell activity, and amnestic effects.
References
- Starec M, Fiserova A, Rosina J, Malek J, Krsiak M: Effect of agroclavine on NK activity in vivo under normal and stress conditions in rats. Physiol Res. 2001;50(5):513-9. [11702856 ]
- General Function:
- G-protein coupled amine receptor activity
- Specific Function:
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
- Gene Name:
- DRD1
- Uniprot ID:
- P21728
- Molecular Weight:
- 49292.765 Da
- Mechanism of Action:
- Agroclavin has agonistic activity at the D1 dopamine receptors, causing increases in cyclic AMP levels, increases in NK (natural killer) cell activity, and amnestic effects.
References
- Starec M, Fiserova A, Rosina J, Malek J, Krsiak M: Effect of agroclavine on NK activity in vivo under normal and stress conditions in rats. Physiol Res. 2001;50(5):513-9. [11702856 ]
- 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:
- Agroclavin moderates the activity of the serotonin and noradrenergic systems of the brain by acting as an antagonist and partial agonist of alpha-1 adrenergic receptors.
References
- Pertz H: Naturally occurring clavines: antagonism/partial agonism at 5-HT2A receptors and antagonism at alpha 1-adrenoceptors in blood vessels. Planta Med. 1996 Oct;62(5):387-92. [8923801 ]
- 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:
- Agroclavin moderates the activity of the serotonin and noradrenergic systems of the brain by acting as an antagonist and partial agonist of alpha-1 adrenergic receptors.
References
- Pertz H: Naturally occurring clavines: antagonism/partial agonism at 5-HT2A receptors and antagonism at alpha 1-adrenoceptors in blood vessels. Planta Med. 1996 Oct;62(5):387-92. [8923801 ]
- 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:
- Agroclavin moderates the activity of the serotonin and noradrenergic systems of the brain by acting as an antagonist and partial agonist of alpha-1 adrenergic receptors.
References
- Pertz H: Naturally occurring clavines: antagonism/partial agonism at 5-HT2A receptors and antagonism at alpha 1-adrenoceptors in blood vessels. Planta Med. 1996 Oct;62(5):387-92. [8923801 ]
- 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:
- Agroclavin moderates the activity of the serotonin and noradrenergic systems of the brain by acting as an antagonist and partial agonist of 5-HT2A receptors.
References
- Pertz H: Naturally occurring clavines: antagonism/partial agonism at 5-HT2A receptors and antagonism at alpha 1-adrenoceptors in blood vessels. Planta Med. 1996 Oct;62(5):387-92. [8923801 ]