ContaminantDB: Philanthotoxin

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

Record Information

Version

1.0

Creation Date

2009-07-03 22:18:56 UTC

Update Date

2016-11-09 01:08:40 UTC

Accession Number

CHEM002068

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)

Contaminant Sources

T3DB toxins

Contaminant Type

Amide
Amine
Animal Toxin
Insect Toxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
PTX-4.3.3	MeSH
delta-PTX	MeSH
PTX-433	MeSH
delta-Philanthotoxin	MeSH
Philanthotoxin 433	MeSH
PTX 433	MeSH

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

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

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	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

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

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Philanthotoxin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

180211

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Philanthotoxin (CHEM002068)

Structure for CHEM002068: Philanthotoxin