Delphinine
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Basic Info
| Common Name | Delphinine(F04792) |
| 2D Structure | |
| Description | Delphinine is a plant toxin found in species of Larkspur (Delphinium family). It is related in structure and has similar effects to aconitine, acting as an allosteric modulator of voltage gated sodium channels, and producing hypotension, bradycardia and cardiac arrhythmia. It is highly poisonous, but in very small doses it has some uses in herbal medicine. (L1234) |
| FRCD ID | F04792 |
| CAS Number | 561-07-9 |
| PubChem CID | 441726 |
| Formula | C33H45NO9 |
| IUPAC Name | None |
| InChI Key | REVYTWNGZDPRKE-UWZYQZSNSA-N |
| InChI | InChI=1S/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3/t20-,21+,22+,23-,24+,25+,26-,27?,28-,30+,31+,32-,33+/m1/s1 |
| Canonical SMILES | CC(=O)OC12CC(C3(CC(C1C3OC(=O)C4=CC=CC=C4)C56C(CCC7(C5C(C2C6N(C7)C)OC)COC)OC)O)OC |
| Isomeric SMILES | CC(=O)O[C@]12C[C@@H]([C@]3(C[C@H]([C@@H]1[C@H]3OC(=O)C4=CC=CC=C4)[C@]56[C@H](CC[C@@]7([C@H]5[C@H]([C@H]2C6N(C7)C)OC)COC)OC)O)OC |
| Synonyms |
8-(Acetyloxy)-13-hydroxy-1,6,16-trimethoxy-4-(methoxymethyl)-20-methylaconitan-14-yl benzoate
Delphinine
561-07-9
CHEBI:4384
SCHEMBL1801657
C08677
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Diterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aconitane-type diterpenoid alkaloids |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Aconitane-type diterpenoid alkaloid - Benzoate ester - Quinolidine - Benzoic acid or derivatives - Alkaloid or derivatives - Benzoyl - Azepane - Monocyclic benzene moiety - Benzenoid - Piperidine - Dicarboxylic acid or derivatives - Tertiary alcohol - Cyclic alcohol - Amino acid or derivatives - Carboxylic acid ester - Tertiary aliphatic amine - Tertiary amine - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Dialkyl ether - Ether - Hydrocarbon derivative - Carbonyl group - Alcohol - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Amine - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 599.721 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 10 |
| Complexity | 1130 |
| Monoisotopic Mass | 599.309 |
| Exact Mass | 599.309 |
| XLogP | 1.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 43 |
| Defined Atom Stereocenter Count | 12 |
| Undefined Atom Stereocenter Count | 1 |
| 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+ | 0.9329 |
| Human Intestinal Absorption | HIA+ | 0.8364 |
| Caco-2 Permeability | Caco2+ | 0.5189 |
| P-glycoprotein Substrate | Substrate | 0.8349 |
| P-glycoprotein Inhibitor | Inhibitor | 0.9314 |
| Inhibitor | 0.5610 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.6340 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4930 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8417 |
| CYP450 2D6 Substrate | Non-substrate | 0.7680 |
| CYP450 3A4 Substrate | Substrate | 0.7060 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9237 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9106 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9051 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9169 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5484 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9772 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9507 |
| Non-inhibitor | 0.5361 | |
| AMES Toxicity | Non AMES toxic | 0.7236 |
| Carcinogens | Non-carcinogens | 0.9526 |
| Fish Toxicity | High FHMT | 0.9838 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9930 |
| Honey Bee Toxicity | Low HBT | 0.5223 |
| Biodegradation | Not ready biodegradable | 0.9903 |
| Acute Oral Toxicity | III | 0.3787 |
| Carcinogenicity (Three-class) | Non-required | 0.5842 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1195 | LogS |
| Caco-2 Permeability | 0.9577 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.5838 | LD50, mol/kg |
| Fish Toxicity | 1.1250 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7304 | pIGC50, ug/L |
Targets
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
- Gene Name:
- SCN1A
- Uniprot ID:
- P35498
- Molecular Weight:
- 228969.49 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. Plays a role in neuropathic pain mechanisms.
- Gene Name:
- SCN10A
- Uniprot ID:
- Q9Y5Y9
- Molecular Weight:
- 220623.605 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Also involved, with the contribution of the receptor tyrosine kinase NTRK2, in rapid BDNF-evoked neuronal depolarization.
- Gene Name:
- SCN11A
- Uniprot ID:
- Q9UI33
- Molecular Weight:
- 204919.66 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
- Gene Name:
- SCN2A
- Uniprot ID:
- Q99250
- Molecular Weight:
- 227972.64 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
- Gene Name:
- SCN3A
- Uniprot ID:
- Q9NY46
- Molecular Weight:
- 226291.905 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. This sodium channel may be present in both denervated and innervated skeletal muscle.
- Gene Name:
- SCN4A
- Uniprot ID:
- P35499
- Molecular Weight:
- 208059.175 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity involved in sa node cell action potential
- Specific Function:
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential. Channel inactivation is regulated by intracellular calcium levels.
- Gene Name:
- SCN5A
- Uniprot ID:
- Q14524
- Molecular Weight:
- 226937.475 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-sensitive Na(+) channel isoform. Plays a role in pain mechanisms, especially in the development of inflammatory pain (By similarity).
- Gene Name:
- SCN9A
- Uniprot ID:
- Q15858
- Molecular Weight:
- 226370.175 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity involved in purkinje myocyte action potential
- Specific Function:
- Crucial in the assembly, expression, and functional modulation of the heterotrimeric complex of the sodium channel. The subunit beta-1 can modulate multiple alpha subunit isoforms from brain, skeletal muscle, and heart. Its association with neurofascin may target the sodium channels to the nodes of Ranvier of developing axons and retain these channels at the nodes in mature myelinated axons.Isoform 2: Cell adhesion molecule that plays a critical role in neuronal migration and pathfinding during brain development. Stimulates neurite outgrowth.
- Gene Name:
- SCN1B
- Uniprot ID:
- Q07699
- Molecular Weight:
- 24706.955 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
- Specific Function:
- Crucial in the assembly, expression, and functional modulation of the heterotrimeric complex of the sodium channel. The subunit beta-2 causes an increase in the plasma membrane surface area and in its folding into microvilli. Interacts with TNR may play a crucial role in clustering and regulation of activity of sodium channels at nodes of Ranvier (By similarity).
- Gene Name:
- SCN2B
- Uniprot ID:
- O60939
- Molecular Weight:
- 24325.69 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
- Specific Function:
- Modulates channel gating kinetics. Causes unique persistent sodium currents. Inactivates the sodium channel opening more slowly than the subunit beta-1. Its association with neurofascin may target the sodium channels to the nodes of Ranvier of developing axons and retain these channels at the nodes in mature myelinated axons (By similarity).
- Gene Name:
- SCN3B
- Uniprot ID:
- Q9NY72
- Molecular Weight:
- 24702.08 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
- Specific Function:
- Modulates channel gating kinetics. Causes negative shifts in the voltage dependence of activation of certain alpha sodium channels, but does not affect the voltage dependence of inactivation. Modulates the suceptibility of the sodium channel to inhibition by toxic peptides from spider, scorpion, wasp and sea anemone venom.
- Gene Name:
- SCN4B
- Uniprot ID:
- Q8IWT1
- Molecular Weight:
- 24968.755 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
- Gene Name:
- SCN7A
- Uniprot ID:
- Q01118
- Molecular Weight:
- 193491.605 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. In macrophages and melanoma cells, isoform 5 may participate in the control of podosome and invadopodia formation.
- Gene Name:
- SCN8A
- Uniprot ID:
- Q9UQD0
- Molecular Weight:
- 225278.005 Da
- Mechanism of Action:
- Delphinine acts as an allosteric modulator of voltage gated sodium channels.
References
- Wikipedia. Delphinine. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Delphinine