Lysergol
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Basic Info
| Common Name | Lysergol(F04942) |
| 2D Structure | |
| Description | Lysergol is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi (most within Claviceps), and in the morning glory family of plants (Convolvulaceae), including the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea. As it is derived from dimethylergoline, it is referred to as a clavine. Lysergol can be utilized as an intermediate in the manufacture of some ergoloid medicines. Long term exposure to some ergoline alkaloids can cause ergotism, a disease causing convulsive and gangrenous symptoms. (L1918, L1928) |
| FRCD ID | F04942 |
| CAS Number | 602-85-7 |
| PubChem CID | 14987 |
| Formula | C16H18N2O |
| IUPAC Name | [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]methanol |
| InChI Key | BIXJFIJYBLJTMK-MEBBXXQBSA-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/h2-5,7,10,15,17,19H,6,8-9H2,1H3/t10-,15-/m1/s1 |
| Canonical SMILES | CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)CO |
| Isomeric SMILES | CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)CO |
| Wikipedia | Lysergol |
| Synonyms |
lysergol
602-85-7
Lysergole
UNII-NTR684Z1AZ
NTR684Z1AZ
CHEMBL39947
CHEBI:60528
(6-methyl-9,10-didehydroergolin-8beta-yl)methanol
9,10-Didehydro-6-methyl-8-hydroxymethylergoline
(7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-yl)-methanol
|
| 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 - Indoloquinoline - 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 - Amine - Organopnictogen compound - Alcohol - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Primary alcohol - 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 | 2.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| 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+ | 0.9621 |
| Human Intestinal Absorption | HIA+ | 0.9931 |
| Caco-2 Permeability | Caco2- | 0.6200 |
| P-glycoprotein Substrate | Substrate | 0.8266 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8770 |
| Inhibitor | 0.6622 | |
| Renal Organic Cation Transporter | Inhibitor | 0.6943 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.3945 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8139 |
| CYP450 2D6 Substrate | Non-substrate | 0.7475 |
| CYP450 3A4 Substrate | Substrate | 0.5122 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9106 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9120 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8931 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9026 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8832 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8629 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.6211 |
| Inhibitor | 0.5712 | |
| AMES Toxicity | AMES toxic | 0.7935 |
| Carcinogens | Non-carcinogens | 0.9582 |
| Fish Toxicity | High FHMT | 0.9589 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8161 |
| Honey Bee Toxicity | Low HBT | 0.6481 |
| Biodegradation | Not ready biodegradable | 0.9836 |
| Acute Oral Toxicity | III | 0.5873 |
| Carcinogenicity (Three-class) | Non-required | 0.6403 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.3574 | LogS |
| Caco-2 Permeability | 0.7033 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7487 | LD50, mol/kg |
| Fish Toxicity | 1.2773 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3378 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high. | Forensic Sci Int | 2015 Apr | 25747328 |
| Changes in concentrations of lysergol in urine and prolactin in plasma, rectal temperature and respiration rate in sheep selected for resistance or susceptibility to ryegrass staggers and fed ergovaline. | N Z Vet J | 2011 Sep | 21851300 |
| Electrospray[+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds. | J Mass Spectrom | 2005 Nov | 16278935 |
Targets
- General Function:
- Signal transducer activity
- Specific Function:
- Guanine nucleotide-binding proteins (G proteins) are involved as modulators or transducers in various transmembrane signaling systems.
- Gene Name:
- GNA15
- Uniprot ID:
- P30679
- Molecular Weight:
- 43567.615 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]
- 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
References
- Boess FG, Martin IL: Molecular biology of 5-HT receptors. Neuropharmacology. 1994 Mar-Apr;33(3-4):275-317. [7984267 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and 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.
- Gene Name:
- HTR1E
- Uniprot ID:
- P28566
- Molecular Weight:
- 41681.57 Da
References
- Boess FG, Martin IL: Molecular biology of 5-HT receptors. Neuropharmacology. 1994 Mar-Apr;33(3-4):275-317. [7984267 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 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 a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis.
- Gene Name:
- HTR2C
- Uniprot ID:
- P28335
- Molecular Weight:
- 51820.705 Da
- Mechanism of Action:
- Lysergol moderates the activity of the serotonin and noradrenergic systems of the brain by acting as an antagonist and partial agonist of 5-HT receptors. This also causes vasoconstriction.
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:
- ADRA1A
- Uniprot ID:
- P35348
- Molecular Weight:
- 51486.005 Da
- Mechanism of Action:
- Lysergol 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:
- Lysergol 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:
- Lysergol 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:
- 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:
- Lysergol moderates the activity of the serotonin and noradrenergic systems of the brain by acting as an antagonist and partial agonist of 5-HT receptors. This also causes vasoconstriction.
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:
- Lysergol moderates the activity of the serotonin and noradrenergic systems of the brain by acting as an antagonist and partial agonist of 5-HT receptors. This also causes vasoconstriction.
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:
- Trace-amine receptor activity
- Specific Function:
- Receptor for trace amines, including beta-phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amines, such as epinephrine and histamine and only partially activated by dopamine and serotonine. Trace amines are biogenic amines present in very low levels in mammalian tissues. Although some trace amines have clearly defined roles as neurotransmitters in invertebrates, the extent to which they function as true neurotransmitters in vertebrates has remained speculative. Trace amines are likely to be involved in a variety of physiological functions that have yet to be fully understood. The signal transduced by this receptor is mediated by the G(s)-class of G-proteins which activate adenylate cyclase.
- Gene Name:
- TAAR1
- Uniprot ID:
- Q96RJ0
- Molecular Weight:
- 39091.34 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]