Elymoclavine
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Basic Info
| Common Name | Elymoclavine(F04941) |
| 2D Structure | |
| Description | Elymoclavine 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 | F04941 |
| CAS Number | 548-43-6 |
| PubChem CID | 11051 |
| Formula | C16H18N2O |
| IUPAC Name | (7-methyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl)methanol |
| InChI Key | DAVNRFCJMIONPO-UHFFFAOYSA-N |
| InChI | InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,13,15,17,19H,6,8-9H2,1H3 |
| Canonical SMILES | CN1CC(=CC2C1CC3=CNC4=CC=CC2=C34)CO |
| Isomeric SMILES | CN1CC(=CC2C1CC3=CNC4=CC=CC2=C34)CO |
| Synonyms |
Elymoclavin
Ergoline-8-methanol, 8,9-didehydro-6-methyl-
Elimoclavin
EINECS 208-948-9
NSC 109431
BRN 0030650
8,9-Didehydro-6-methylergoline-8-methanol
ACMC-20ltyg
AC1L1WIH
DAVNRFCJMIONPO-UHFFFAOYSA-N
|
| 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 - Heteroaromatic compound - Pyrrole - 1,3-aminoalcohol - Tertiary aliphatic amine - Tertiary amine - Azacycle - Organoheterocyclic compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Alcohol - Organooxygen compound - Organic oxygen compound - Organic nitrogen compound - Primary alcohol - Organopnictogen 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 | 254.333 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Complexity | 394 |
| Monoisotopic Mass | 254.142 |
| Exact Mass | 254.142 |
| XLogP | 1.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| 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+ | 0.9513 |
| Human Intestinal Absorption | HIA+ | 0.9913 |
| Caco-2 Permeability | Caco2- | 0.6071 |
| P-glycoprotein Substrate | Substrate | 0.8378 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8541 |
| Inhibitor | 0.6437 | |
| Renal Organic Cation Transporter | Inhibitor | 0.6801 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4022 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7989 |
| CYP450 2D6 Substrate | Non-substrate | 0.7290 |
| CYP450 3A4 Substrate | Non-substrate | 0.5055 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8891 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9118 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8574 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8952 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8856 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8606 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.6209 |
| Inhibitor | 0.5988 | |
| AMES Toxicity | AMES toxic | 0.8137 |
| Carcinogens | Non-carcinogens | 0.9570 |
| Fish Toxicity | High FHMT | 0.9271 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8083 |
| Honey Bee Toxicity | Low HBT | 0.6601 |
| Biodegradation | Not ready biodegradable | 0.9836 |
| Acute Oral Toxicity | III | 0.5871 |
| Carcinogenicity (Three-class) | Non-required | 0.6547 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.2795 | LogS |
| Caco-2 Permeability | 0.6740 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7374 | LD50, mol/kg |
| Fish Toxicity | 1.2998 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3216 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| In silico genotoxicity and carcinogenicity prediction for food-relevant secondary plant metabolites. | Food Chem Toxicol | 2018 Jun | 29660365 |
| Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high. | Forensic Sci Int | 2015 Apr | 25747328 |
| 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 |
| Analysis of endophyte toxins: fescue and other grasses toxic to livestock. | J Anim Sci | 1995 Mar | 7608022 |
Targets
- 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:
- Elymoclavine 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:
- 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:
- Elymoclavine has agonistic activity at the D1 dopamine receptors, causing increases in cyclic AMP levels and increases in NK (natural killer) cell activity.
References
- Fiserova A, Kovaru H, Hajduova Z, Mares V, Starec M, Kren V, Flieger M, Pospisil: Neuroimmunomodulation of natural killer (NK) cells by ergot alkaloid derivatives. Physiol Res. 1997;46(2):119-25. [9727503 ]
- 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:
- Elymoclavine has agonistic activity at the D1 dopamine receptors, causing increases in cyclic AMP levels and increases in NK (natural killer) cell activity.
References
- Fiserova A, Kovaru H, Hajduova Z, Mares V, Starec M, Kren V, Flieger M, Pospisil: Neuroimmunomodulation of natural killer (NK) cells by ergot alkaloid derivatives. Physiol Res. 1997;46(2):119-25. [9727503 ]
- 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:
- Elymoclavine 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:
- Elymoclavine 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:
- Elymoclavine 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 ]