Name: A 83586C
Rating: 5 (10 reviews)

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HIT ID:HIT212711906
Cas No:116364-81-9
常用名:A 83586C
别名:A-83586C, A83586C
IUPAC:(2S)-2-[(2R,5S,6S)-6-[(2E,4S,6E)-4,6-dimethyl-5-oxoocta-2,6-dien-2-yl]-2-hydroxy-5-methyloxan-2-yl]-2-hydroxy-N-[(3R,6S,9R,16S,17S,20R,23S)-7-hydroxy-20-[(1S)-1-hydroxyethyl]-3,4,6-trimethyl-2,5,8,15,19,22-hexaoxo-17-(propan-2-yl)-18-oxa-1,4,7,13,14,21,27-heptaazatricyclo[21.4.0.0^{9,14}]heptacosan-16-yl]butanamide
IUPAC:(2S)-2-[(2R,5S,6S)-6-[(2E,4S,6E)-4,6-dimethyl-5-oxoocta-2,6-dien-2-yl]-2-hydroxy-5-methyloxan-2-yl]-2-hydroxy-N-[(3R,6S,9R,16S,17S,20R,23S)-7-hydroxy-20-[(1S)-1-hydroxyethyl]-3,4,6-trimethyl-2,5,8,15,19,22-hexaoxo-17-(propan-2-yl)-18-oxa-1,4,7,13,14,21,27-heptaazatricyclo[21.4.0.0^{9,14}]heptacosan-16-yl]butanamide
InChI key:BJRNAAQGIMGUML-IYSUCPQHSA-N

分子式:C47H76N8O14
分子量:977.167
氢键供体数 (HBD):8
氢键受体数 (HBA):15
LogP:1.1378827
SMILES:CC[C@@](O)(C(=O)N[C@H]1[C@@H](OC(=O)[C@H](NC(=O)[C@@H]2CCCNN2C(=O)[C@@H](C)N(C)C(=O)[C@H](C)N(O)C(=O)[C@H]2CCCNN2C1=O)[C@H](C)O)C(C)C)[C@@]1(O)CC[C@H](C)[C@H](O1)C(\C)=C\[C@H](C)C(=O)C(\C)=C\C
SMILES:CC[C@@](O)(C(=O)N[C@H]1[C@@H](OC(=O)[C@H](NC(=O)[C@@H]2CCCNN2C(=O)[C@@H](C)N(C)C(=O)[C@H](C)N(O)C(=O)[C@H]2CCCNN2C1=O)[C@H](C)O)C(C)C)[C@@]1(O)CC[C@H](C)[C@H](O1)C(\C)=C\[C@H](C)C(=O)C(\C)=C\C

A-83586C is a depsipeptide antibiotic from Streptomyces karnatakensis with potent against Gram-positive activity in vitro. A-83586C acts as a highly potent inhibitor of beta-catenin/TCF4 signaling within cancer cells, while simultaneously downregulating osteopontin (Opn) expression. A-83586C also inhibits E2F-mediated transcription by downregulating E2F1 expression and inducing dephosphorylation of the oncogenic hyperphosphorylated retinoblastoma protein (pRb).

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