ContaminantDB: Paxilline

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (27)XML

Record Information

Version

1.0

Creation Date

2010-06-10 15:41:05 UTC

Update Date

2026-03-31 19:04:18 UTC

Accession Number

CHEM002744

Identification

Common Name

Paxilline

Class

Small Molecule

Description

Tremorgenic agent from Penicillium paxilli, Acremonium lorii, Emericella foveolata, Emericella desertorum and Emericella striata Paxilline is a potassium channel blocker. Paxilline is a toxic, tremorgenic indole alkaloid produced by Penicillium paxilli. Paxilline belongs to the family of Diterpenes. These are terpene compounds formed by four isoprene units.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Ester
Ether
Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Paxillin	MeSH

Chemical Formula

C₂₇H₃₃NO₄

Average Molecular Mass

435.555 g/mol

Monoisotopic Mass

435.241 g/mol

CAS Registry Number

57186-25-1

IUPAC Name

11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

Traditional Name

11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

SMILES

CC(C)(O)C1OC2CCC3(C)C4(C)C(CC5=C4NC4=CC=CC=C54)CCC3(O)C2=CC1=O

InChI Identifier

InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3

InChI Key

ACNHBCIZLNNLRS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
3-alkylindole
Indole
Indole or derivatives
Dihydropyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Cyclic alcohol
Cyclic ketone
Ketone
Oxacycle
Azacycle
Dialkyl ether
Ether
Alcohol
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

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	252°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	4.38	ALOGPS
logP	3.62	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.56	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	123.22 m³·mol⁻¹	ChemAxon
Polarizability	50.05 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-014r-0001900000-6e471bdc1ff96e73b30b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-0202900000-03386f50a5cbb076e63e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-5609200000-48b4d94ea4a2c3facc8a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1001900000-54d37f6b4afc84835df5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lr-3003900000-1da697d4a85ac38b1ace	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0159-3319000000-600bb923dd46e122c54d	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (6)

Mechanism of Toxicity

Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. In addition, paxilline inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. Paxilline is also genotoxic and causes DNA damage. (2, 3, 4)

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

Paxilline is a tremorgenic mycotoxin that has been found in fungus Penicillium paxilli. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (2, 5)

Minimum Risk Level

Not Available

Health Effects

Tremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (2)

Symptoms

Tremorgenic mycotoxins affect central nervous system activity, inducing neurologic symptoms including mental confusion, paralysis, tremors, seizures, and death. They cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors, hyperexcitability, convulsions and ataxia. (2)

Treatment

To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (1)

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

Paxilline

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

4697

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

Paxilline (CHEM002744)

Structure for CHEM002744: Paxilline