59795-94-7
Chemical Structure
Neoaureothin
Synonym(s): NSC 260179; Spectinabilin
- CAS No.: 59795-94-7
- Formula:C28H31NO6
- Molecular Weight:477.55
IUPAC Name: 2-methoxy-3,5-dimethyl-6-((R,Z)-4-((2E,4E,6E)-2,4,6-trimethyl-7-(4-nitrophenyl)hepta-2,4,6-trien-1-ylidene)tetrahydrofuran-2-yl)-4H-pyran-4-one
InChIKey: IZICQJAGBLBAMJ-QDYRYYKCSA-N
SMILES: CC(C1=O)=C([C@@](OC/2)([H])CC2=C\C(C)=C\C(C)=C\C(C)=C\C(C=C3)=CC=C3[N+]([O-])=O)OC(OC)=C1C
Biological Activity: Neoaureothin is a bacterial metabolite that has been found in Streptomyces. It is an androgen receptor (AR) antagonist that inhibits binding of dihydrotestosterone (DHT) to ARs (IC50=13 μM) and inhibits DHT-induced expression of prostate-specific antigen in LNCaP cells (IC50=1.75 nM). Neoaureothin is cytotoxic to A549, HCT116, and HepG2 cells (IC50s=34.3, 47, and 37.2 μg/mL, respectively). It also has nematocidal activity against the pine wood nematode B. xylophilus (LC50=0.84 μg/mL) and increases survival of P. densiflora trees inoculated with B. xylophilus.
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Neoaureothin | Neoaureothin is a bacterial metabolite that has been found in Streptomyces. It is an androgen receptor (AR) antagonist that inhibits binding of dihydrotestosterone (DHT) to ARs (IC50=13 μM) and inhibits DHT-induced expression of prostate-specific antigen in LNCaP cells (IC50=1.75 nM). Neoaureothin is cytotoxic to A549, HCT116, and HepG2 cells (IC50s=34.3, 47, and 37.2 μg/mL, respectively). It also has nematocidal activity against the pine wood nematode B. xylophilus (LC50=0.84 μg/mL) and increases survival of P. densiflora trees inoculated with B. xylophilus. | |||||||||||||||||||||
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