Asteltoxin

Basic Info

Common NameAsteltoxin(F04994)
2D Structure
Description

Asteltoxin 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.

FRCD IDF04994
CAS Number79663-49-3
PubChem CID6438150
FormulaC23H30O7
IUPAC Name

6-[(1E,3E,5E)-6-[(2R,3R,3aR,4R,5R,6aS)-2-ethyl-3,4-dihydroxy-3,3a-dimethyl-2,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]hexa-1,3,5-trienyl]-4-methoxy-5-methylpyran-2-one

InChI Key

GPXPJKFETRLRAS-AHUKKWBBSA-N

InChI

InChI=1S/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+/t16-,18-,20+,21+,22+,23+/m1/s1

Canonical SMILES

CCC1C(C2(C(C(OC2O1)C=CC=CC=CC3=C(C(=CC(=O)O3)OC)C)O)C)(C)O

Isomeric SMILES

CC[C@@H]1[C@]([C@]2([C@H]([C@H](O[C@H]2O1)/C=C/C=C/C=C/C3=C(C(=CC(=O)O3)OC)C)O)C)(C)O

Synonyms
        
            Asteltoxin
        
            EV-Toxin
        
            79663-49-3
        
            2H-Pyran-2-one, 6-(6-(hexahydro-3,4-dihydroxy-3a,4-dimethyl-5-ethylfuro(2,3-b)furan-2-yl)-1,3,5-hexatrienyl)-4-methoxy-5-methyl-, (2R-(2-alpha(1E,3E,5E),3-alpha,3a-beta,4-beta,5-beta,6a-beta))-
        
            AC1O5P4J
        
            AC1Q2C8J
        
            CHEMBL3758613
        
            ZINC1574763
        
            MCULE-3646908430
        
            LS-127447
Classifies
                

                  
                    Fungal Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassFurofurans
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentFurofurans
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsFurofuran - Alkyl aryl ether - Pyranone - Monosaccharide - Pyran - Vinylogous ester - Tetrahydrofuran - Tertiary alcohol - Heteroaromatic compound - Secondary alcohol - Lactone - Acetal - Ether - Oxacycle - Alcohol - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organic oxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight418.486
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Complexity837
Monoisotopic Mass418.199
Exact Mass418.199
XLogP2.1
Formal Charge0
Heavy Atom Count30
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.5000
Human Intestinal AbsorptionHIA+0.9224
Caco-2 PermeabilityCaco2-0.6515
P-glycoprotein SubstrateSubstrate0.7346
P-glycoprotein InhibitorNon-inhibitor0.5515
Non-inhibitor0.7882
Renal Organic Cation TransporterNon-inhibitor0.9277
Distribution
Subcellular localizationMitochondria0.5586
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8313
CYP450 2D6 SubstrateNon-substrate0.8644
CYP450 3A4 SubstrateSubstrate0.5589
CYP450 1A2 InhibitorNon-inhibitor0.7468
CYP450 2C9 InhibitorNon-inhibitor0.8456
CYP450 2D6 InhibitorNon-inhibitor0.9168
CYP450 2C19 InhibitorNon-inhibitor0.7672
CYP450 3A4 InhibitorNon-inhibitor0.8122
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6524
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9843
Non-inhibitor0.9242
AMES ToxicityAMES toxic0.8121
CarcinogensNon-carcinogens0.9482
Fish ToxicityHigh FHMT0.8587
Tetrahymena Pyriformis ToxicityHigh TPT0.9989
Honey Bee ToxicityHigh HBT0.8290
BiodegradationNot ready biodegradable0.9732
Acute Oral ToxicityIII0.4045
Carcinogenicity (Three-class)Non-required0.4784
Model Value Unit
Absorption
Aqueous solubility-3.1728LogS
Caco-2 Permeability0.2436LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.2317LD50, mol/kg
Fish Toxicity0.5896pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.0532pIGC50, ug/L

References

TitleJournalDatePubmed ID
Emericella venezuelensis, a new species with stellate ascospores producing sterigmatocystin and aflatoxin B1.Syst Appl Microbiol2004 Nov15612624

Targets

Target Details

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
Mechanism of Action:
Asteltoxin inhibits mitochondrial respiration by affecting its energy transfer system. It does this by inhibiting Mg2+ and Na+/K+-ATPases.
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
Target Details

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
Mechanism of Action:
Asteltoxin inhibits mitochondrial respiration by affecting its energy transfer system. It does this by inhibiting Mg2+ and Na+/K+-ATPases.
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
Target Details

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
Mechanism of Action:
Asteltoxin inhibits mitochondrial respiration by affecting its energy transfer system. It does this by inhibiting Mg2+ and Na+/K+-ATPases.
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
Target Details

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
Mechanism of Action:
Asteltoxin inhibits mitochondrial respiration by affecting its energy transfer system. It does this by inhibiting Mg2+ and Na+/K+-ATPases.
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
Target Details

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
Mechanism of Action:
Asteltoxin inhibits mitochondrial respiration by affecting its energy transfer system. It does this by inhibiting Mg2+ and Na+/K+-ATPases.
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
Target Details

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
Mechanism of Action:
Asteltoxin inhibits mitochondrial respiration by affecting its energy transfer system. It does this by inhibiting Mg2+ and Na+/K+-ATPases.
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
Target Details

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
Mechanism of Action:
Asteltoxin inhibits mitochondrial respiration by affecting its energy transfer system. It does this by inhibiting Mg2+ and Na+/K+-ATPases.
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
Target Details

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
Mechanism of Action:
Asteltoxin inhibits mitochondrial respiration by affecting its energy transfer system. It does this by inhibiting Mg2+ and Na+/K+-ATPases.
References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]