Asteltoxin (T3D3749)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (8)XML
Targets (8)
Record Information
Version2.0
Creation Date2010-05-12 16:57:23 UTC
Update Date2014-12-24 20:26:29 UTC
Accession NumberT3D3749
Identification
Common NameAsteltoxin
ClassSmall Molecule
DescriptionAsteltoxin is a mycotoxin of Aspergillus stellatus and Emericella varicolor Asteltoxin belongs to the family of Furofurans. These are organic compounds containing a two furan rings fused to each other.
Compound Type
  • Ester
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Ev-toxin
Chemical FormulaC23H30O7
Average Molecular Mass418.480 g/mol
Monoisotopic Mass418.199 g/mol
CAS Registry Number79663-49-3
IUPAC Name6-[(1E,3E,5E)-6-{5-ethyl-3,4-dihydroxy-3a,4-dimethyl-hexahydrofuro[2,3-b]furan-2-yl}hexa-1,3,5-trien-1-yl]-4-methoxy-5-methyl-2H-pyran-2-one
Traditional Name6-[(1E,3E,5E)-6-{5-ethyl-3,4-dihydroxy-3a,4-dimethyl-tetrahydrofuro[2,3-b]furan-2-yl}hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one
SMILES[H]/C(=C(/[H])\C(\[H])=C(/[H])C1=C(C)C(OC)=CC(=O)O1)/C(/[H])=C(\[H])C1OC2OC(CC)C(C)(O)C2(C)C1O
InChI IdentifierInChI=1/C23H30O7/c1-6-18-23(4,26)22(3)20(25)16(29-21(22)30-18)12-10-8-7-9-11-15-14(2)17(27-5)13-19(24)28-15/h7-13,16,18,20-21,25-26H,6H2,1-5H3/b8-7+,11-9+,12-10+
InChI KeyInChIKey=GPXPJKFETRLRAS-BGSVYHRFNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurofurans
Sub ClassNot Available
Direct ParentFurofurans
Alternative Parents
Substituents
  • Furofuran
  • Pyranone
  • Alkyl aryl ether
  • Pyran
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • Secondary alcohol
  • Lactone
  • Oxacycle
  • Ether
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point130 - 132°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP3.51ALOGPS
logP2.48ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.13ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity116.22 m³·mol⁻¹ChemAxon
Polarizability45.88 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1020900000-f9179a3ad1ad5107b1c92016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbc-4293400000-45089c3f901a8272a3a32016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9010000000-6001d45f3353a2f103f42016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0106900000-6b12da5504b033c2e2a62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-9827600000-35580e00304cc0ec3ae42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-5910000000-a627aefa8f04d3abed972016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (3)
Mechanism of ToxicityAsteltoxin inhibits mitochondrial respiration by affecting its energy transfer system. It does this by inhibiting Mg2+ and Na+/K+-ATPases. (1, 4, 2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseLD50: 5.9 mg/kg (Intraperitoneal, Mouse) (2)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAsteltoxin is a mycotoxin produced by the fungi Aspergillus stellatus and Emericella variecolor. It can be found in contaminated corn crops. (2)
Minimum Risk LevelNot Available
Health EffectsAsteltoxin affects the central nervous system. (2)
SymptomsAsteltoxin can cause respiratory arrest and paralysis. (2)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB29464
PubChem Compound ID6438150
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
  2. Kawai K, Fukushima H, Nozawa Y: Inhibition of mitochondrial respiration by asteltoxin, a respiratory toxin from Emericella variecolor. Toxicol Lett. 1985 Nov;28(2-3):73-7. [3000028 ]
  3. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  4. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Sodium/potassium-transporting ATPase subunit alpha-1
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular Weight:
112895.01 Da
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
  2. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  3. Kawai K, Fukushima H, Nozawa Y: Inhibition of mitochondrial respiration by asteltoxin, a respiratory toxin from Emericella variecolor. Toxicol Lett. 1985 Nov;28(2-3):73-7. [3000028 ]
Target Details
2. Sodium/potassium-transporting ATPase subunit alpha-2
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A2
Uniprot ID:
P50993
Molecular Weight:
112264.385 Da
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
  2. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  3. Kawai K, Fukushima H, Nozawa Y: Inhibition of mitochondrial respiration by asteltoxin, a respiratory toxin from Emericella variecolor. Toxicol Lett. 1985 Nov;28(2-3):73-7. [3000028 ]
Target Details
3. Sodium/potassium-transporting ATPase subunit alpha-3
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A3
Uniprot ID:
P13637
Molecular Weight:
111747.51 Da
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
  2. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  3. Kawai K, Fukushima H, Nozawa Y: Inhibition of mitochondrial respiration by asteltoxin, a respiratory toxin from Emericella variecolor. Toxicol Lett. 1985 Nov;28(2-3):73-7. [3000028 ]
Target Details
4. Sodium/potassium-transporting ATPase subunit alpha-4
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients. Plays a role in sperm motility.
Gene Name:
ATP1A4
Uniprot ID:
Q13733
Molecular Weight:
114165.44 Da
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
  2. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  3. Kawai K, Fukushima H, Nozawa Y: Inhibition of mitochondrial respiration by asteltoxin, a respiratory toxin from Emericella variecolor. Toxicol Lett. 1985 Nov;28(2-3):73-7. [3000028 ]
Target Details
5. Sodium/potassium-transporting ATPase subunit beta-1
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The beta subunit regulates, through assembly of alpha/beta heterodimers, the number of sodium pumps transported to the plasma membrane.Involved in cell adhesion and establishing epithelial cell polarity.
Gene Name:
ATP1B1
Uniprot ID:
P05026
Molecular Weight:
35061.07 Da
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
  2. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  3. Kawai K, Fukushima H, Nozawa Y: Inhibition of mitochondrial respiration by asteltoxin, a respiratory toxin from Emericella variecolor. Toxicol Lett. 1985 Nov;28(2-3):73-7. [3000028 ]
Target Details
6. Sodium/potassium-transporting ATPase subunit beta-2
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-2 subunit is not known.Mediates cell adhesion of neurons and astrocytes, and promotes neurite outgrowth.
Gene Name:
ATP1B2
Uniprot ID:
P14415
Molecular Weight:
33366.925 Da
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
  2. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  3. Kawai K, Fukushima H, Nozawa Y: Inhibition of mitochondrial respiration by asteltoxin, a respiratory toxin from Emericella variecolor. Toxicol Lett. 1985 Nov;28(2-3):73-7. [3000028 ]
Target Details
7. Sodium/potassium-transporting ATPase subunit beta-3
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-3 subunit is not known.
Gene Name:
ATP1B3
Uniprot ID:
P54709
Molecular Weight:
31512.34 Da
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
  2. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  3. Kawai K, Fukushima H, Nozawa Y: Inhibition of mitochondrial respiration by asteltoxin, a respiratory toxin from Emericella variecolor. Toxicol Lett. 1985 Nov;28(2-3):73-7. [3000028 ]
Target Details
8. Sodium/potassium-transporting ATPase subunit gamma
General Function:
Transporter activity
Specific Function:
May be involved in forming the receptor site for cardiac glycoside binding or may modulate the transport function of the sodium ATPase.
Gene Name:
FXYD2
Uniprot ID:
P54710
Molecular Weight:
7283.265 Da
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
  2. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  3. Kawai K, Fukushima H, Nozawa Y: Inhibition of mitochondrial respiration by asteltoxin, a respiratory toxin from Emericella variecolor. Toxicol Lett. 1985 Nov;28(2-3):73-7. [3000028 ]