rac 8-Prenylnaringenin
rac 8-Prenylnaringenin structure
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Common Name | rac 8-Prenylnaringenin | ||
|---|---|---|---|---|
| CAS Number | 68682-02-0 | Molecular Weight | 340.37000 | |
| Density | N/A | Boiling Point | N/A | |
| Molecular Formula | C20H20O5 | Melting Point | N/A | |
| MSDS | N/A | Flash Point | N/A | |
Use of rac 8-Prenylnaringenin(±)-8-Prenylnaringenin, a natural prenylated flavonoid, is a potent phytoestrogen. (±)-8-Prenylnaringenin is an orally active selective estrogen receptor modulator (SERM) (Estrogen Receptor/ERR) that inhibits ERα and ERβ with IC50s of 57 nM and 68 nM, respectively. (±)-8-Prenylnaringenin has anticancer effects, and can be used for osteoporosis research[1][2]. |
Summary: rac 8-Prenylnaringenin, Chinese name: 8-Prenylnaringenin, CAS number: 68682-02-0, molecular formula: C20H20O5, molecular weight: 340.37000. This product is a light yellow powder. For research-use only, not for medical or clinical usage.
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | rac 8-Prenylnaringenin |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | (±)-8-Prenylnaringenin, a natural prenylated flavonoid, is a potent phytoestrogen. (±)-8-Prenylnaringenin is an orally active selective estrogen receptor modulator (SERM) (Estrogen Receptor/ERR) that inhibits ERα and ERβ with IC50s of 57 nM and 68 nM, respectively. (±)-8-Prenylnaringenin has anticancer effects, and can be used for osteoporosis research[1][2]. |
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| Related Catalog | |
| Target |
ERα:57 nM (IC50) ERβ:68 nM (IC50) |
| In Vitro | 在兔骨髓细胞中，(±)-8-Prenylnaringenin 比 Osteoclasts 更能抑制破骨细胞的形成并诱导破骨细胞凋亡。(±)-8-Prenylnaringenin 应用于 MC3T3-E1 成骨细胞系，可促进分化和成熟，同时抑制 RAW264.7 破骨细胞系的分化。(±)-8-Prenylnaringenin 抑制核因子-κB配体受体激活剂 (RANKL) 的表达，并导致骨保护素的表达增加[1]。 在暴露于 (±)-8-Prenylnaringenin 后，在 PC-3 人前列腺癌细胞和 UO.31 人肾癌细胞中观察到显着的剂量依赖性增殖抑制。在人乳腺癌细胞系 MCF-10A 中，(±)-8-Prenylnaringenin 调节雌二醇转化为促癌代谢物的代谢途径，从而抑制恶性转化[1]。 |
| In Vivo | (±)-8-Prenylnaringenin（50 mg/kg；口服强饲法；每天一次；持续 12 天）改善由 STZ 治疗引起的葡萄糖稳态受损和胰岛功能障碍。 (±)-8-Prenylnaringenin 增加胰腺和肝脏中 ERα 和肝脏中成纤维细胞生长因子 21 的蛋白表达水平[3]。 Animal Model: Male C57BL/6J mice (Seven-week-old) injected with Streptozotocin (STZ)[3] Dosage: 50 mg/kg Administration: Orally gavage; once daily; for 12 days Result: Ameliorated impaired glucose homeostasis and islet dysfunction induced by STZ treatment. |
| References |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| Molecular Formula | C20H20O5 |
|---|---|
| Molecular Weight | 340.37000 |
| Exact Mass | 340.13100 |
| PSA | 86.99000 |
| LogP | 4.01860 |
| Appearance of Characters | Light yellow powder |
| InChIKey | LPEPZZAVFJPLNZ-UHFFFAOYSA-N |
| SMILES | CC(C)=CCc1c(O)cc(O)c2c1OC(c1ccc(O)cc1)CC2=O |
| Storage condition | −20°C |
This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| Safety Phrases | 22-24/25 |
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| WGK Germany | 3 |
This table contains target information, in‑vitro & in‑vivo assay data for this compound.
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Name: Primary cell-based high-throughput screening assay for identification of compounds th...
Source: Johns Hopkins Ion Channel Center
Target: regulator of G-protein signaling 4 isoform 2 [Homo sapiens]
External Id: JHICC_RGS_Act_HTS
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Name: Luminescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: mu-type opioid receptor isoform MOR-1 [Homo sapiens]
External Id: OPRM1-OPRD1_AG_LUMI_1536_1X%ACT PRUN
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Name: QFRET-based biochemical primary high throughput screening assay to identify exosite i...
Source: The Scripps Research Institute Molecular Screening Center
Target: disintegrin and metalloproteinase domain-containing protein 17 preproprotein [Homo sapiens]
External Id: ADAM17_INH_QFRET_1536_1X%INH PRUN
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Name: Inhibition of porcine pancreatic lipase at 100 ug/ml pre-incubated for 15 mins before...
Source: ChEMBL
Target: Pancreatic triacylglycerol lipase
External Id: CHEMBL3610637
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Name: Luminescence Cell-Free Homogeneous Counter Screen to Identify Inhibitors of ADP-glo R...
Source: Broad Institute
Target: N/A
External Id: 2046-03_INHIBITORS_DOSE-TITRATION_MLPCN-CHERRYPICK
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Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN
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Name: uHTS identification of small molecule activators of the adaptive arm of the Unfolded ...
Source: Burnham Center for Chemical Genomics
Target: N/A
External Id: BCCG-A405-UPR-XBP1-PrimaryAgonist-Assay
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Name: Inhibition of porcine pancreatic lipase pre-incubated for 15 mins before p-nitropheny...
Source: ChEMBL
Target: Pancreatic triacylglycerol lipase
External Id: CHEMBL3610636
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Name: Luminescence Cell-Free Homogeneous Dose Retest to Identify Inhibitors of Glycogen Syn...
Source: Broad Institute
Target: glycogen synthase kinase 3 beta isoform 1 [Homo sapiens]
External Id: 2046-02_INHIBITORS_DOSE-TITRATION_MLPCN-CHERRYPICK
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Name: Fluorescence polarization to screen for inhibitor that competite the binding of FadD2...
Source: Broad Institute
Target: FATTY-ACID-CoA LIGASE FADD28 (FATTY-ACID-CoA SYNTHETASE)
External Id: 2147-01_Inhibitor_SinglePoint_HTS_Activity
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This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What is the molecular weight of rac 8-Prenylnaringenin? |
| A: Molecular weight of rac 8-Prenylnaringenin is 340.37000. |
| Q: What is the physical appearance of rac 8-Prenylnaringenin? |
| A: rac 8-Prenylnaringenin appears as Light yellow powder. |
| Q: What English synonyms does rac 8-Prenylnaringenin have? |
| A: English synonyms of rac 8-Prenylnaringenin: 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one. |
| Q: What is the SMILES notation of rac 8-Prenylnaringenin? |
| A: SMILES notation of rac 8-Prenylnaringenin is CC(C)=CCc1c(O)cc(O)c2c1OC(c1ccc(O)cc1)CC2=O. |
| Q: What is the LogP of rac 8-Prenylnaringenin? |
| A: LogP of rac 8-Prenylnaringenin is 4.01860. |
| Q: What are the storage conditions for rac 8-Prenylnaringenin? |
| A: Storage conditions for rac 8-Prenylnaringenin: −20°C. |
| Q: What are the uses of rac 8-Prenylnaringenin? |
| A: Main uses of rac 8-Prenylnaringenin: (±)-8-Prenylnaringenin, a natural prenylated flavonoid, is a potent phytoestrogen. (±)-8-Prenylnaringenin is an orally active selective estrogen receptor modulator (SERM) (Estrogen Receptor/ERR) that inhibits ERα and ERβ with IC50s of 57 nM and 68 nM, respectively. (±)-8-Prenylnaringenin has anticancer effects, and can be used for osteoporosis research[1][2]. |
| Q: What is the InChIKey of rac 8-Prenylnaringenin? |
| A: InChIKey of rac 8-Prenylnaringenin is LPEPZZAVFJPLNZ-UHFFFAOYSA-N. |
| Q: What is the polar surface area (PSA) of rac 8-Prenylnaringenin? |
| A: Polar surface area (PSA) of rac 8-Prenylnaringenin is 86.99000. |
| Q: What is the molecular formula of rac 8-Prenylnaringenin? |
| A: Molecular formula of rac 8-Prenylnaringenin is C20H20O5. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |