T3DB: Philanthotoxin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (9)XML

Targets (9)

Record Information

Version

2.0

Creation Date

2009-07-03 22:18:56 UTC

Update Date

2014-12-24 20:25:35 UTC

Accession Number

T3D2489

Identification

Common Name

Philanthotoxin

Class

Small Molecule

Description

Philanthotoxins are components of the venom of the Egyptian solitary wasp (Philanthus triangulum). They are four types of philantothoxins, alpha, beta, gamma, and delta. (1)

Compound Type

Amide
Amine
Animal Toxin
Insect Toxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Delta-philanthotoxin
Delta-PTX
Philanthotoxin 433

Chemical Formula

C₂₃H₄₁N₅O₃

Average Molecular Mass

435.603 g/mol

Monoisotopic Mass

435.321 g/mol

CAS Registry Number

77108-00-0

IUPAC Name

N-(1-{[4-({3-[(3-aminopropyl)amino]propyl}amino)butyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl)butanamide

Traditional Name

philanthotoxin

SMILES

CCCC(=O)NC(CC1=CC=C(O)C=C1)C(=O)NCCCCNCCCNCCCN

InChI Identifier

InChI=1S/C23H41N5O3/c1-2-7-22(30)28-21(18-19-8-10-20(29)11-9-19)23(31)27-17-4-3-13-25-15-6-16-26-14-5-12-24/h8-11,21,25-26,29H,2-7,12-18,24H2,1H3,(H,27,31)(H,28,30)

InChI Key

InChIKey=VRQNABCCOFCGJL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Amphetamine or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Fatty amide
N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Secondary amine
Secondary aliphatic amine
Organic oxide
Organic oxygen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Amine
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	0.97	ALOGPS
logP	-0.94	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	10.92	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	128.51 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	125.13 m³·mol⁻¹	ChemAxon
Polarizability	52.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0n2i-3687900000-ebf404c51909f3c6dc9c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zgi-5951000000-2dda16a9c92f5d2e6b6b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-7920000000-c3ff9e72f278e8fa2403	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2033900000-102641a59abd3468fdfd	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0wni-7496400000-015ae2347be3179aa4fb	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0016-9610000000-5756bbb6866a47212740	2016-08-03	View Spectrum

Toxicity Profile

Route of Exposure

Injection (sting/bite) (2)

Mechanism of Toxicity

Philanthotoxins block glutamate receptors, especially the calcium permeable AMPA receptor and kainate receptor. (1)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Philanthotoxins are components of the venom of the Egyptian solitary wasp (Philanthus triangulum). (1)

Minimum Risk Level

Not Available

Health Effects

Philanthotoxins are neurotoxic. (1)

Symptoms

Wasp and bee stings cause local pain and swelling. In some individuals an allergic reaction may result, which is usually anaphylactic and can be deadly. (3)

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

115201

ChEMBL ID

Not Available

ChemSpider ID

Not Available

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

C034092

Stitch ID

Philanthotoxin

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D2489.pdf

General References

Wikipedia. Philanthotoxin. Last Updated 6 May 2009. [Link]
Wikipedia. Insect toxins. Last Updated 19 February 2009. [Link]
Wikipedia. Bee sting. Last Updated 5 August 2009. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Glutamate receptor 1

General Function:: Pdz domain binding
Specific Function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. In the presence of CACNG4 or CACNG7 or CACNG8, shows resensitization which is characterized by a delayed accumulation of current flux upon continued application of glutamate.
Gene Name:: GRIA1
Uniprot ID:: P42261
Molecular Weight:: 101505.245 Da

References

Wikipedia. Philanthotoxin. Last Updated 6 May 2009. [Link]

Target Details

2. Glutamate receptor 2

General Function:: Ionotropic glutamate receptor activity
Specific Function:: Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. In the presence of CACNG4 or CACNG7 or CACNG8, shows resensitization which is characterized by a delayed accumulation of current flux upon continued application of glutamate.
Gene Name:: GRIA2
Uniprot ID:: P42262
Molecular Weight:: 98820.32 Da

References

Wikipedia. Philanthotoxin. Last Updated 6 May 2009. [Link]

Target Details

3. Glutamate receptor 3

General Function:: Extracellular-glutamate-gated ion channel activity
Specific Function:: Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. In the presence of CACNG4 or CACNG7 or CACNG8, shows resensitization which is characterized by a delayed accumulation of current flux upon continued application of glutamate.
Gene Name:: GRIA3
Uniprot ID:: P42263
Molecular Weight:: 101155.975 Da

References

Wikipedia. Philanthotoxin. Last Updated 6 May 2009. [Link]

Target Details

4. Glutamate receptor 4

General Function:: Ionotropic glutamate receptor activity
Specific Function:: Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. In the presence of CACNG4 or CACNG7 or CACNG8, shows resensitization which is characterized by a delayed accumulation of current flux upon continued application of glutamate.
Gene Name:: GRIA4
Uniprot ID:: P48058
Molecular Weight:: 100870.085 Da

References

Wikipedia. Philanthotoxin. Last Updated 6 May 2009. [Link]

Target Details

5. Glutamate receptor ionotropic, kainate 1

General Function:: Voltage-gated cation channel activity
Specific Function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus.
Gene Name:: GRIK1
Uniprot ID:: P39086
Molecular Weight:: 103979.665 Da

References

Wikipedia. Philanthotoxin. Last Updated 6 May 2009. [Link]

Target Details

6. Glutamate receptor ionotropic, kainate 2

General Function:: Kainate selective glutamate receptor activity
Specific Function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus. Modulates cell surface expression of NETO2 (By similarity).
Gene Name:: GRIK2
Uniprot ID:: Q13002
Molecular Weight:: 102582.475 Da

References

Wikipedia. Philanthotoxin. Last Updated 6 May 2009. [Link]

Target Details

7. Glutamate receptor ionotropic, kainate 3

General Function:: Kainate selective glutamate receptor activity
Specific Function:: Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. The postsynaptic actions of Glu are mediated by a variety of receptors that are named according to their selective agonists. This receptor binds domoate > kainate >> L-glutamate = quisqualate >> AMPA = NMDA.
Gene Name:: GRIK3
Uniprot ID:: Q13003
Molecular Weight:: 104036.06 Da

References

Wikipedia. Philanthotoxin. Last Updated 6 May 2009. [Link]

Target Details

8. Glutamate receptor ionotropic, kainate 4

General Function:: Kainate selective glutamate receptor activity
Specific Function:: Receptor for glutamate. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. The postsynaptic actions of Glu are mediated by a variety of receptors that are named according to their selective agonists.
Gene Name:: GRIK4
Uniprot ID:: Q16099
Molecular Weight:: 107244.485 Da

References

Wikipedia. Philanthotoxin. Last Updated 6 May 2009. [Link]

Target Details

9. Glutamate receptor ionotropic, kainate 5

General Function:: Kainate selective glutamate receptor activity
Specific Function:: Receptor for glutamate. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. The postsynaptic actions of Glu are mediated by a variety of receptors that are named according to their selective agonists. This receptor binds kainate > quisqualate > domoate > L-glutamate >> AMPA >> NMDA = 1S,3R-ACPD.
Gene Name:: GRIK5
Uniprot ID:: Q16478
Molecular Weight:: 109263.695 Da

References

Wikipedia. Philanthotoxin. Last Updated 6 May 2009. [Link]

Philanthotoxin (T3D2489)

Structure for T3D2489: Philanthotoxin

Targets

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