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Basic Description
| Synonyms | C09187 | INDOLO(2',3':3,4)PYRIDO(2,1-B)QUINAZOLIN-5(7H)-ONE, 8,13,13B,14-TETRAHYDRO-14-METHYL-, (13BS)- | DTXSID10966123 | VS-12304 | (S)-14-methyl-8,13,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one | (1S)-21-methyl-3,13,21-triazapen |
|---|---|
| Specifications & Purity | analytical standard, ≥99% |
| Biochemical and Physiological Mechanisms | The interferon-γ priming signal regulating the transcriptional activation of the iNOS gene is blocked by Evodiamine, suppressing iNOS protein synthesis but not affecting iNOS function. Evodiamine also demonstrates antiangiogenesis through inhibition of va |
| Storage Temp | Protected from light,Desiccated |
| Shipped In | Normal |
| Grade | analytical standard |
| Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
| Product Description | Evodiamine is a quinozole alkaloid isolated from Evodia rutaecarpa, described as an agonist of the VR1 (vanilloid receptor subtype 1, TRPV1) with affinity (Ki = 5.95 microM) comparable to that of the prototypical VR1 chemical activator Capsaicin .Evodiamine induction of 45Ca2+ uptake was competitively antagonized by the Capsaicin antagonist Capsazepine .Evodiamine is described to inhibit prostaglandin E2 synthesis, cyclooxygenase-2 induction and NF-κB activation, producing antiinflammatory effects. |
Associated Targets(Human)
PDE5A Tclin Phosphodiesterase 5A (5113 Activities)
TOP1 Tclin DNA topoisomerase I (7553 Activities)
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MCF7 (126967 Activities)
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A549 (127892 Activities)
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HCT-116 (91556 Activities)
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HepG2 (196354 Activities)
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MDA-MB-435 (38290 Activities)
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SIRT3 Tchem NAD-dependent deacetylase sirtuin 3 (1285 Activities)
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SIRT2 Tchem NAD-dependent deacetylase sirtuin 2 (3979 Activities)
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SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)
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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
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MSTO-211H (316 Activities)
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Associated Targets(non-human)
rep Replicase polyprotein 1ab (378 Activities)
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Names and Identifiers
| IUPAC Name | (1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one |
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| INCHI | InChI=1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3/t18-/m0/s1 |
| InChi Key | TXDUTHBFYKGSAH-SFHVURJKSA-N |
| Canonical SMILES | CN1C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3 |
| Isomeric SMILES | CN1[C@@H]2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3 |
| PubChem CID | 442088 |
| Molecular Weight | 303.36 |
Certificates
Certificate of Analysis(COA)
Enter Lot Number to search for COA:
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 I2123147 | Certificate of Analysis | Jun 16, 2023 | E101966 |
Chemical and Physical Properties
| Solubility | Soluble in DMSO (5 mg/mL,warm to 40°C), water (<1 mg/mL) at 25 °C, and ethanol (<1 mg/mL) at 25 °C |
|---|---|
| Sensitivity | Light sensitive. |
| Melt Point(°C) | 278°C |
Safety and Hazards(GHS)
| Pictogram(s) | GHS06 |
|---|---|
| Signal | Danger |
| Hazard Statements | H300:Fatal if swallowed |
| Precautionary Statements | P301+P310:IF SWALLOWED: Immediately call a POISON CENTER/doctor/... P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P270:Do not eat, drink or smoke when using this product. P330:Rinse mouth. |
Related Documents
FAQs and Articles
FAQ
Citations of This Product
| 1. Yun Yang, Yuan Xiong, Guanghao Zhu, Mengru Sun, Kun Zou, Yitian Zhao, Yong Zhang, Zhijian Xu, Yiming Li, Weiliang Zhu, Qi Jia, Bo Li, Guangbo Ge. (2023) Discovery of seven-membered ring berberine analogues as highly potent and specific hCES2A inhibitors. CHEMICO-BIOLOGICAL INTERACTIONS, 378 (110501). [PMID:37080375] [10.1016/j.cbi.2023.110501] |
| 2. Ruifeng Liang, Wenjing Ge, Bingjie Li, Weifeng Cui, Xiaofan Ma, Yuying Pan, Gengsheng Li. (2022) Evodiamine decreased the systemic exposure of pravastatin in non-alcoholic steatohepatitis rats due to the up-regulation of hepatic OATPs. PHARMACEUTICAL BIOLOGY, 60 (1): (359-373). [PMID:35171063] [10.1080/13880209.2022.2036767] |
| 3. Li Chen-Guang, Zeng Qiong-Zhen, Chen Ming-Ye, Xu Li-Hui, Zhang Cheng-Cheng, Mai Feng-Yi, Zeng Chen-Ying, He Xian-Hui, Ouyang Dong-Yun. (2019) Evodiamine Augments NLRP3 Inflammasome Activation and Anti-bacterial Responses Through Inducing α-Tubulin Acetylation. Frontiers in Pharmacology, 10 (290). [PMID:30971927] [10.3389/fphar.2019.00290] |
| 4. Li Yang-ling, Pan Yi-ni, Wu Wen-jue, Mao Shi-ying, Sun Jiao, Zhao Yi-ming, Dong Jing-yin, Zhang Da-yong, Pan Jian-ping, Zhang Chong, Lin Neng-ming. (2016) Evodiamine induces apoptosis and enhances apoptotic effects of erlotinib in wild-type EGFR NSCLC cells via S6K1-mediated Mcl-1 inhibition. MEDICAL ONCOLOGY, 33 (2): (1-9). [PMID:26757927] [10.1007/s12032-015-0726-4] |
| 5. Lushan Yu, Zhangting Wang, Minmin Huang, Yingying Li, Kui Zeng, Jinxiu Lei, Haihong Hu, Baian Chen, Jing Lu, Wen Xie, Su Zeng. (2016) Evodia alkaloids suppress gluconeogenesis and lipogenesis by activating the constitutive androstane receptor. Biochimica et Biophysica Acta-Gene Regulatory Mechanisms, 1859 (1100). [PMID:26455953] [10.1016/j.bbagrm.2015.10.001] |
| 6. Junyan Wang, Minmin Huang, Haihong Hu, Lushan Yu, Su Zeng. (2014) Pregnane X receptor-mediated transcriptional activation of UDP-glucuronosyltransferase 1A1 by natural constituents from foods and herbs. FOOD CHEMISTRY, 164 (74). [PMID:24996308] [10.1016/j.foodchem.2014.05.004] |
| 7. Zhang Chunhua, Wu Huiqin, Huang Xiaolan, Zhu Zhixin, Luo Huitai, Huang Fang, Lin Xiaoshan. (2012) Simultaneous Determination of Toxic Alkaloids in Blood and Urine by HPLC–ESI–MS/MS. CHROMATOGRAPHIA, 75 (9): (499-511). [PMID:] [10.1007/s10337-012-2216-6] |
References
| 1. Yun Yang, Yuan Xiong, Guanghao Zhu, Mengru Sun, Kun Zou, Yitian Zhao, Yong Zhang, Zhijian Xu, Yiming Li, Weiliang Zhu, Qi Jia, Bo Li, Guangbo Ge. (2023) Discovery of seven-membered ring berberine analogues as highly potent and specific hCES2A inhibitors. CHEMICO-BIOLOGICAL INTERACTIONS, 378 (110501). [PMID:37080375] [10.1016/j.cbi.2023.110501] |
| 2. Ruifeng Liang, Wenjing Ge, Bingjie Li, Weifeng Cui, Xiaofan Ma, Yuying Pan, Gengsheng Li. (2022) Evodiamine decreased the systemic exposure of pravastatin in non-alcoholic steatohepatitis rats due to the up-regulation of hepatic OATPs. PHARMACEUTICAL BIOLOGY, 60 (1): (359-373). [PMID:35171063] [10.1080/13880209.2022.2036767] |
| 3. Li Chen-Guang, Zeng Qiong-Zhen, Chen Ming-Ye, Xu Li-Hui, Zhang Cheng-Cheng, Mai Feng-Yi, Zeng Chen-Ying, He Xian-Hui, Ouyang Dong-Yun. (2019) Evodiamine Augments NLRP3 Inflammasome Activation and Anti-bacterial Responses Through Inducing α-Tubulin Acetylation. Frontiers in Pharmacology, 10 (290). [PMID:30971927] [10.3389/fphar.2019.00290] |
| 4. Li Yang-ling, Pan Yi-ni, Wu Wen-jue, Mao Shi-ying, Sun Jiao, Zhao Yi-ming, Dong Jing-yin, Zhang Da-yong, Pan Jian-ping, Zhang Chong, Lin Neng-ming. (2016) Evodiamine induces apoptosis and enhances apoptotic effects of erlotinib in wild-type EGFR NSCLC cells via S6K1-mediated Mcl-1 inhibition. MEDICAL ONCOLOGY, 33 (2): (1-9). [PMID:26757927] [10.1007/s12032-015-0726-4] |
| 5. Lushan Yu, Zhangting Wang, Minmin Huang, Yingying Li, Kui Zeng, Jinxiu Lei, Haihong Hu, Baian Chen, Jing Lu, Wen Xie, Su Zeng. (2016) Evodia alkaloids suppress gluconeogenesis and lipogenesis by activating the constitutive androstane receptor. Biochimica et Biophysica Acta-Gene Regulatory Mechanisms, 1859 (1100). [PMID:26455953] [10.1016/j.bbagrm.2015.10.001] |
| 6. Junyan Wang, Minmin Huang, Haihong Hu, Lushan Yu, Su Zeng. (2014) Pregnane X receptor-mediated transcriptional activation of UDP-glucuronosyltransferase 1A1 by natural constituents from foods and herbs. FOOD CHEMISTRY, 164 (74). [PMID:24996308] [10.1016/j.foodchem.2014.05.004] |
| 7. Zhang Chunhua, Wu Huiqin, Huang Xiaolan, Zhu Zhixin, Luo Huitai, Huang Fang, Lin Xiaoshan. (2012) Simultaneous Determination of Toxic Alkaloids in Blood and Urine by HPLC–ESI–MS/MS. CHROMATOGRAPHIA, 75 (9): (499-511). [PMID:] [10.1007/s10337-012-2216-6] |