Aurovertin B
Basic information
- CAS
55350-03-3- Standard SMILES
CC[C@H]1O[C@]2(C)[C@H](OC(C)=O)[C@@]1(C)O[C@@H](/C=C/C=C/C=C/c1oc(=O)cc(OC)c1C)[C@@H]2O- InChIKey
QXCOFYWOWZJFEA-YJMRODJJSA-N- Molecular formula
- C25H32O8
- Average molar mass
- 460.5 g/mol
- Monoisotopic mass
- 460.20971797
Overview
AUROVERTIN B has been reported in Calcarisporium arbuscula, Albatrellopsis confluens, and Albatrellus confluens with data available.
Names & identifiers
- Preferred name
- Aurovertin B
- IUPAC
- [(1S,3S,4S,5S,7R,8S)-7-ethyl-4-hydroxy-3-[(1E,3E,5E)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trienyl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl] acetate
Names & synonyms
aurovertin bAurovertin-B55350-03-3DTXSID001017654RefChem:560357DTXCID6014758347-ethyl-4-hydroxy-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[(1S,3S,4S,5S,7R,8S)-7-ethyl-4-hydroxy-3-[(1E,3E,5E)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trienyl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl] acetateSCHEMBL21067566DB07394AURNS00071822
Show more names
Q27096613(1S)-4-O-acetyl-1,5:3,6-dianhydro-7,8-dideoxy-1-[(1E,3E,5E)-6-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)hexa-1,3,5-trien-1-yl]-3,5-dimethyl-D-glycero-L-talo-octitol
Database identifiers
- CAS
55350-03-3- PubChem CID
- 444853
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 8
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 942
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information
2H-Pyran-2-one, 6-(6-(8-(acetyloxy)-7-ethyl-4-hydroxy-1,5-dimethyl-2,6-dioxabicyclo(3.2.1)oct-3-yl)-1,3,5-hexatrienyl)-4-methoxy-5-methyl-, (1S-(1-alpha,3-alpha(1E,3E,5E),4-beta,5-alpha-7-beta))-: Does not have an individual approval but may be used under an appropriate group standard
Toxicology
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
Aurovertins 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. (A3032, A3033, A3034)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Uses & manufacturing
UsesAurovertin B is a mycotoxin and antibiotic produced by the fungus Calcarisporium arbuscula. (A3002)
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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