Record Information
Version2.0
Creation Date2010-05-12 17:31:41 UTC
Update Date2014-12-24 20:26:29 UTC
Accession NumberT3D3751
Identification
Common NameAurovertin D
ClassSmall Molecule
DescriptionAurovertin B is a mycotoxin and antibiotic produced by the fungus Calcarisporium arbuscula. It is known for its ability to inhibit oxidative phosphorylation. (1, 2)
Compound Type
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
3-O-Acetyl-1,4:2,6-dianhydro-1-(1-hydroxyethyl)-6-[(1E,3E,5E)-6-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)-1,3,5-hexatrien-1-yl]-2,4-dimethylhexitol
6-(6-(8-(acetyloxy)-4-hydroxy-7-(1-hydroxyethyl)-1,5-dimethyl-2,6-dioxabicyclo(3.2.1)oct-3-yl)-1,3,5-hexatrienyl)-4-methoxy-5-methyl-2H-Pyran-2-one
Chemical FormulaC25H32O9
Average Molecular Mass476.516 g/mol
Monoisotopic Mass476.205 g/mol
CAS Registry Number65256-31-7
IUPAC Name4-hydroxy-7-(1-hydroxyethyl)-3-[6-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate
Traditional Name4-hydroxy-7-(1-hydroxyethyl)-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate
SMILESCOC1=CC(=O)OC(C=CC=CC=CC2OC3(C)C(OC(C)(C3OC(C)=O)C2O)C(C)O)=C1C
InChI IdentifierInChI=1S/C25H32O9/c1-14-17(32-20(28)13-19(14)30-6)11-9-7-8-10-12-18-21(29)24(4)23(31-16(3)27)25(5,33-18)22(34-24)15(2)26/h7-13,15,18,21-23,26,29H,1-6H3/b8-7+,11-9+,12-10-
InChI KeyInChIKey=UKPVUEBWITXZRF-CDIKDJIESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentC-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • 1,4-dioxepane
  • Alkyl aryl ether
  • Pyranone
  • Dioxepane
  • Pyran
  • Oxane
  • Heteroaromatic compound
  • Vinylogous ester
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Dialkyl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
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 PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP3.4ALOGPS
logP1.4ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.9ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.75 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity126.94 m³·mol⁻¹ChemAxon
Polarizability50.55 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, Positivesplash10-05r0-0000900000-bb400c331e266d623f892019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-0353900000-a6d03b6bab21fa7c71ca2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9041200000-a4f31519914e10a6c9492019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-1000900000-077889ff93a5a8e725112019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6210900000-76f45cdeb2fbf8356d592019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9101100000-210f0312d3a0ccc878782019-02-23View Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (5)
Mechanism of ToxicityAurovertins are a mixed, noncompetitive inhibitors of both ATP hydrolysis and synthesis. They do this by inhibiting the proton-pumping F1F0-ATP synthase by binding to beta-subunits in its F1 catalytic sector. F1F0-ATP synthase is responsible for the terminal step of oxidative phosphorylation. Each ATP synthase complex has three beta subunits, and aurovertins are believed to bind with varying affinity to two subunits on sites in a cleft between the nucleotide-binding and C-terminal domains, thus preventing closure of the catalytic interfaces necessary for the cyclic interconversion of catalytic sites. (2, 3, 4)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAurovertin D is a mycotoxin and antibiotic produced by the fungus Calcarisporium arbuscula. (1)
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6438901
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. Johnson KM, Swenson L, Opipari AW Jr, Reuter R, Zarrabi N, Fierke CA, Borsch M, Glick GD: Mechanistic basis for differential inhibition of the F1Fo-ATPase by aurovertin. Biopolymers. 2009 Oct;91(10):830-40. doi: 10.1002/bip.21262. [19462418 ]
  3. van Raaij MJ, Abrahams JP, Leslie AG, Walker JE: The structure of bovine F1-ATPase complexed with the antibiotic inhibitor aurovertin B. Proc Natl Acad Sci U S A. 1996 Jul 9;93(14):6913-7. [8692918 ]
  4. Gledhill JR, Walker JE: Inhibitors of the catalytic domain of mitochondrial ATP synthase. Biochem Soc Trans. 2006 Nov;34(Pt 5):989-92. [17052243 ]
  5. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Transporter activity
Specific Function:
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked together by a central stalk and a peripheral stalk. During catalysis, ATP synthesis in the catalytic domain of F(1) is coupled via a rotary mechanism of the central stalk subunits to proton translocation. Subunits alpha and beta form the catalytic core in F(1). Rotation of the central stalk against the surrounding alpha(3)beta(3) subunits leads to hydrolysis of ATP in three separate catalytic sites on the beta subunits.
Gene Name:
ATP5B
Uniprot ID:
P06576
Molecular Weight:
56559.42 Da
References
  1. Johnson KM, Swenson L, Opipari AW Jr, Reuter R, Zarrabi N, Fierke CA, Borsch M, Glick GD: Mechanistic basis for differential inhibition of the F1Fo-ATPase by aurovertin. Biopolymers. 2009 Oct;91(10):830-40. doi: 10.1002/bip.21262. [19462418 ]
  2. van Raaij MJ, Abrahams JP, Leslie AG, Walker JE: The structure of bovine F1-ATPase complexed with the antibiotic inhibitor aurovertin B. Proc Natl Acad Sci U S A. 1996 Jul 9;93(14):6913-7. [8692918 ]
  3. Gledhill JR, Walker JE: Inhibitors of the catalytic domain of mitochondrial ATP synthase. Biochem Soc Trans. 2006 Nov;34(Pt 5):989-92. [17052243 ]