Thielavin A
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Grundinformationen
- CAS
71950-66-8- Standard-SMILES
Cc1cc(O)c(C)c(O)c1C(=O)Oc1c(C)c(C)c(C(=O)Oc2c(C)c(C)c(C(=O)O)c(O)c2C)c(O)c1C- InChIKey
MGGMNKJGDSNTKZ-UHFFFAOYSA-N- Summenformel
- C29H30O10
- Durchschnittliche Molmasse
- 538,549 g/mol
- Monoisotopische Masse
- 538,18389716
Namen und Bezeichner
- Bevorzugter Name
- Thielavin A
- IUPAC
- 4-({4-[(2,4-Dihydroxy-3,6-dimethylbenzoyl)oxy]-2-hydroxy-3,5,6-trimethylbenzoyl}oxy)-2-hydroxy-3,5,6-trimethylbenzoic acid
- Englischer Name
- thielavin A
- Summenformel
- C29H30O10
- Molmasse
- 538.54
Namen und Synonyme
thielavin A4-[(2,4-Dihydroxy-3,6-dimethylbenzoyl)oxy]-2-hydroxy-3,5,6-trimethylbenzoic acid 4-carboxy-3-hydroxy-2,5,6-trimethylphenyl esterBenzoic acid, 4-[(2,4-dihydroxy-3,6-dimethylbenzoyl)oxy]-2-hydroxy-3,5,6-trimethyl-, 4-carboxy-3-hydroxy-2,5,6-trimethylphenyl ester
Datenbank-Bezeichner
- CAS
71950-66-8- PubChem CID
- 194424
- DTXSID
DTXSID10222236- ChEBI
CHEBI:212063- Nikkaji
- J133.882J
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 235 · 235-236 °C
- Siedepunkt
- 850 · 850.0±65.0 °C(Predicted)
- Dichte
- 1.371 · 1.371±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- DMF: souble; DMSO: souble; Ethanol: soluble
- Aggregatzustand
- White to off-white powder.
- pka
- 2.82 · 2.82±0.28(Predicted)
Chemie und Industrie
Anwendungen
BeschreibungThielavin A is a fungal metabolite originally isolated from T. terricola that is related to thielavin B . Thielavin A inhibits COX, blocking both the conversion of arachidonic acid to prostaglandin H2 (PGH2; ) and the conversion of PGH2 to PGE2 (; IC50s = 10 and 40 μM, respectively). Thielavin A also inhibits glucose-6-phosphatase in rat liver microsomes (IC50 = 4.6 μM). It is a non-competitive inhibitor of α-glucosidase from S. cerevisiae (IC50 = 23.8 μM; Ki = 27.8 μM).
VerwendenThe fungal metabolite, thielavin A, and its relatives are glucose-6-phosphatase inhibitors. The three benzoic acid units are essential for inhibition. Thielavin A was originally isolated as a inhibitor of prostaglandin biosynthesis. The closely related thielavin B is a telomerase and cell wall transglycosylation inhibitor.
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