Aurovertin D (CHEM002719)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2010-05-12 17:31:41 UTC
Update Date2026-04-06 13:15:08 UTC
Accession NumberCHEM002719
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)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Hydroxy-7-(1-hydroxyethyl)-3-[(1Z,3E,5E)-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 acetic acidGenerator
Chemical FormulaC25H32O9
Average Molecular Mass476.522 g/mol
Monoisotopic Mass476.205 g/mol
CAS Registry Number65256-31-7
IUPAC Name4-hydroxy-7-(1-hydroxyethyl)-3-[(1Z,3E,5E)-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-[(1Z,3E,5E)-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
SMILES[H]/C(=C(/[H])\C(\[H])=C(/[H])C1=C(C)C(OC)=CC(=O)O1)/C(/[H])=C(/[H])C1OC2(C)C(OC(C)(C2OC(C)=O)C1O)C(C)O
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 KeyUKPVUEBWITXZRF-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
  • Pyranone
  • Dioxepane
  • Alkyl aryl ether
  • 1,4-dioxepane
  • Pyran
  • Oxane
  • Heteroaromatic compound
  • Vinylogous ester
  • Tetrahydrofuran
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • 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
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
Polarizability50.5 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05r0-0000900000-96dd09a16ab013275931Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ldi-0164900000-817c4db2203b9e1d0acbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btc-9061100000-80e8de3470aca3c73a21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-1010900000-5a89afeb6d38734ae5c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-7210900000-75f89f749fd7af51b387Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9101000000-7e456ac079cfa1d02997Spectrum
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
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available