Evodiamine - analytical standard, ≥99% , CAS No.518-17-2

CAS: 518-17-2 Cat. No.: E101966 Peso molecular: 303.36 Número EC: 637-111-4

GRADE & PURITY Analytical standard, ≥99%

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

Storage

Protected from light,Desiccated,Room temperature

Shipped In

Normal

Descripción general

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.

Specifications

Sinónimos

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

Especificaciones y pureza

analytical standard, ≥99%

Mecanismos bioquímicos y fisiológicos

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

Condiciones de almacenamiento de almacenamiento

Protected from light, Desiccated, Room temperature

Enviado en

Normal

Grado

Analytical standard

Nota

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.

Pureza

≥99%

Nombres e identificadores

• Pubchem Sid: 504758777
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758777
• Sonrisas canónicas: CN1C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
• 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
• InChIKey: TXDUTHBFYKGSAH-SFHVURJKSA-N
• 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
• Isómeros SMILES: CN1[C@@H]2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
• Peso molecular: 303.36
• Reaxy-Rn: 94484
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=94484&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Indoles and derivatives
      • Subclass Pyridoindoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Indoles and derivatives
• Subclass: Pyridoindoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Beta carbolines
• Alternative Parents: Quinazolines 3-alkylindoles Dialkylarylamines Benzenoids Vinylogous amides Tertiary carboxylic acid amides Pyrroles Heteroaromatic compounds Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Beta-carboline - Diazanaphthalene - Quinazoline - 3-alkylindole - Indole - Dialkylarylamine - Benzenoid - Pyrrole - Tertiary carboxylic acid amide - Vinylogous amide - Heteroaromatic compound - Lactam - Carboxamide group - Carboxylic acid derivative - Azacycle - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as beta carbolines. These are compounds containing a 9H-pyrido[3,4-b]indole moiety.
• External Descriptors: Quinazoline alkaloids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

Discover Target: PDE5A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TOP1 Tclin DNA topoisomerase I (7553 Activities)

Discover Target: TOP1

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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)

Discover Target: SIRT3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SIRT2 Tchem NAD-dependent deacetylase sirtuin 2 (3979 Activities)

Discover Target: SIRT2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)

Discover Target: SIRT1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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MSTO-211H (316 Activities)

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Objetivos asociados (no humanos)

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: 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
• Sensibilidad: Light sensitive.
• Punto de fusión (°C): 278°C
• Peso molecular: 303.400 g/mol
• XLogP3: 3.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 303.137 Da
• Monoisotopic Mass: 303.137 Da
• Topological Polar Surface Area: 39.300 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 495.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

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,      [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,      [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,      [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.  (2015)  Evodia alkaloids suppress gluconeogenesis and lipogenesis by activating the constitutive androstane receptor.  Biochimica et Biophysica Acta-Gene Regulatory Mechanisms,      [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,      [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]

8. Huiying Wu, Lei Zeng, Mengling Wei, Liwei Chen, Jiajia Guo, Yun Huang, Fuhou Lei, Hao Li.  (2025)  Preparation of mixed-mode chromatographic stationary phases based on modified rosin and its application in the separation of natural medicines.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.114110]

9. Boda Li, Junpeng Liu, Di Zhang, Yiran Chu, Zeying Chen, Jiaruei Tsao, Taige Chen, Jiaxuan Jiang, Kai Hu.  (2025)  Evodiamine Promotes Autophagy and Alleviates Oxidative Stress in Dry Eye Disease Through the p53/mTOR Pathway.  INVESTIGATIVE OPHTHALMOLOGY & VISUAL SCIENCE,  66  (3): (44-44).  [PMID:40111353] [10.1167/iovs.66.3.44]

10. Wang Pu, Sun Congcong, Shi Chao, Gao Yong, Luan Chunyu, Yan Chao.  (2025)  Evodiamine alleviates IL-1β-induced chondrocyte damage by regulating mitochondrial dysfunction via the SIRT1/PGC-1α pathway.  JOURNAL OF MOLECULAR HISTOLOGY,  56  (6): (1-14).  [PMID:41186656] [10.1007/s10735-025-10640-y]