Rutaecarpine - ≥98% , CAS No.84-26-4

CAS: 84-26-4 Cat. No.: R107338 Peso molecular: 287.32 Número EC: 635-907-6 PubChem CID: 65752

GRADE & PURITY ≥98%

Synonyms

C18H13N3O | SMR001230721 | RUTECARPINE [MI] | Indolo[2',4]pyrido[2,1-b]quinazolin-5(7H)-one, 8,13-dihydro- | Rutaecarpine, >98% (HPLC) | cid_65752 | Rutacarpine | Rutaecarpin | UPCMLD-DP040 | HMS3884P13 | EN300-302963 | Rutecarpine | SW220226-1 | HMS3656C

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Sinónimos

C18H13N3O | SMR001230721 | RUTECARPINE [MI] | Indolo[2', 4]pyrido[2, 1-b]quinazolin-5(7H)-one, 8, 13-dihydro- | Rutaecarpine, >98% (HPLC) | cid_65752 | Rutacarpine | Rutaecarpin | UPCMLD-DP040 | HMS3884P13 | EN300-302963 | Rutecarpine | SW220226-1 | HMS3656C

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

Indoloquinazoline alkaloid derived from Evodia rutaecarpa . Various pharmacological actions in vitro and in vivo; anti-inflammatory, antinociceptive, vasorelaxant, antiplatelet aggregation. Pharmacologically active following oral administration.

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

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. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504754006
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504754006
• Sonrisas canónicas: C1CN2C(=NC3=CC=CC=C3C2=O)C4=C1C5=CC=CC=C5N4
• IUPAC Name: 3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one
• InChIKey: ACVGWSKVRYFWRP-UHFFFAOYSA-N
• INCHI: 1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2
• Isómeros SMILES: C1CN2C(=NC3=CC=CC=C3C2=O)C4=C1C5=CC=CC=C5N4
• WGK Alemania: 3
• PubChem CID: 65752
• Número ONU: 2811
• Peso molecular: 287.32

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 Pyridopyrimidines 3-alkylindoles Pyrimidones Pyridines and derivatives Benzenoids Pyrroles Heteroaromatic compounds Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Beta-carboline - Diazanaphthalene - Pyridopyrimidine - 3-alkylindole - Quinazoline - Indole - Pyrimidone - Pyridine - Benzenoid - Pyrimidine - Heteroaromatic compound - Pyrrole - Lactam - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - 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)

CYP1A2 Tchem Cytochrome P450 1A2 (2 Activities)

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CYP1B1 Tchem Cytochrome P450 1B1 (2 Activities)

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PTGS2 Tclin Prostaglandin G/H synthase 2 (2 Activities)

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CYP1A1 Tchem Cytochrome P450 1A1 (1 Activities)

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PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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CYP1B1 Tchem Cytochrome P450 1B1 (1148 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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TRPV1 Tclin Vanilloid receptor (8273 Activities)

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APP Tclin Amyloid-beta A4 protein (8510 Activities)

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ALB Tchem Serum albumin (2651 Activities)

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ARSA Tbio Cerebroside-sulfatase (655 Activities)

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CYP1A1 Tchem Cytochrome P450 1A1 (1169 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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NR1H2 Tchem LXR-beta (3841 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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Huh-7 (12904 Activities)

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K562 (73714 Activities)

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KM12 (47707 Activities)

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M14 (47487 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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RKO (1376 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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SF-295 (48000 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SK-OV-3 (52876 Activities)

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SNB-19 (46794 Activities)

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SW480 (6023 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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UO-31 (46270 Activities)

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Objetivos asociados (no humanos)

ampC Beta-lactamase AmpC (62480 Activities)

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Cruzipain (33337 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Plasmodium falciparum (966862 Activities)

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Rattus norvegicus (775804 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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BCHE Cholinesterase (8742 Activities)

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Danio rerio (3092 Activities)

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Aorta (2975 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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FTL Ferritin light chain (43324 Activities)

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PGAM 2,3-bisphosphoglycerate-independent phosphoglycerate mutase (46 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Very slightly soluble in Ether,Chloroform,Benzene,Alcohol
• Sensibilidad: Heat Sensitive
• Punto de fusión (°C): 262 °C
• Peso molecular: 287.300 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 287.106 Da
• Monoisotopic Mass: 287.106 Da
• Topological Polar Surface Area: 48.500 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 516.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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. Xue-qi Liu, Juan Jin, Zeng Li, Ling Jiang, Yu-hang Dong, Yu-ting Cai, Ming-fei Wu, Jia-nan Wang, Tao-tao Ma, Jia-gen Wen, Ming-ming Liu, Jun Li, Yong-gui Wu, Xiao-ming Meng.  (2020)  Rutaecarpine derivative Cpd-6c alleviates acute kidney injury by targeting PDE4B, a key enzyme mediating inflammation in cisplatin nephropathy.  BIOCHEMICAL PHARMACOLOGY,      [PMID:32622666] [10.1016/j.bcp.2020.114132]

3. Yao Sun, Pengfei Li, Ting Wang, Liting Qin, Gege Cheng, Liqun Shen, Xingdong Yao, Shaoping Wei, Jianxin Jiang, Fuhou Lei.  (2019)  Alkaloid purification using rosin-based polymer-bonded silica stationary phase in HPLC.  JOURNAL OF SEPARATION SCIENCE,  42  (24): (3646-3652).  [PMID:31613051] [10.1002/jssc.201900835]

4. 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]

5. 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]

6. Jiahui Wang, Min Zhou, Rong Fu, Ju Ge, Wei Yang, Xufeng Hong, Congli Sun, Xiaobin Liao, Yan Zhao, Zhaoyang Wang.  (2024)  Iron Molybdenum Sulfide-Supported Ultrafine Ru Nanoclusters for Robust Sulfion Degradation-Assisted Hydrogen Production.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202315326]

7. Yan Liu, Feng Qi, Lun-Jian Xiang, Zhu-Jun Yi, Sheng-Wei Li.  (2025)  Rutaecarpine alleviates hepatic ischemia‒reperfusion injury in liver transplantation by inhibiting inflammatory response and oxidative stress.  Frontiers in Pharmacology,      [PMID:39963247] [10.3389/fphar.2025.1539744]

8. Juan Chen, Zi-yun Hu, Yu Ma, Shan Jiang, Jiu-yu Yin, Yu-kai Wang, Yong-gui Wu, Xue-qi Liu.  (2024)  Rutaecarpine alleviates inflammation and fibrosis by targeting CK2α in diabetic nephropathy.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:39353318] [10.1016/j.biopha.2024.117499]

9. Xin Li, Aiyu Niu, Shanshan Yang, Fei Liu.  (2024)  The reduction of nitrobenzene by Fe(II)-goethite-hematite heterogeneous systems: Insight from thermodynamic parameters of reduction potential.  JOURNAL OF ENVIRONMENTAL MANAGEMENT,      [PMID:39250851] [10.1016/j.jenvman.2024.122404]

10. 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]