Peiminine - 10mM in DMSO , CAS No.18059-10-4

CAS: 18059-10-4 Cat. No.: P422213 Peso molecular: 429.64 Número EC: 683-180-9

GRADE & PURITY 10mM in DMSO

Synonyms

IMPERIALINE [MI] | 3beta,20-Dihydroxy-5alpha-cevan-6-one | Cevan-6-one, 3,20-dihydroxy-, (3.beta.,5.alpha.)- | QUB07U6VTQ | CCG-208360 | Fritillarine | HY-N0213 | Verticinone;Raddeanine | P2609 | Peininine ,(S) | UNII-QUB07U6VTQ | DTXSID80939349 | Peimini

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Sinónimos

IMPERIALINE [MI] | 3beta, 20-Dihydroxy-5alpha-cevan-6-one | Cevan-6-one, 3, 20-dihydroxy-, (3.beta., 5.alpha.)- | QUB07U6VTQ | CCG-208360 | Fritillarine | HY-N0213 | Verticinone;Raddeanine | P2609 | Peininine , (S) | UNII-QUB07U6VTQ | DTXSID80939349 | Peimini

Especificaciones y pureza

10mM in DMSO

Mecanismos bioquímicos y fisiológicos

Anti-inflammatory agent. Inhibits TGF-β, CTGF, ERK1/2, NF-κB and FasL pathways. Shows antitussive and anti-inflammatory effects in vivo. Orally active.

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

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

Nombres e identificadores

• Sonrisas canónicas: CC1CCC2C(C3CCC4C(C3CN2C1)CC5C4CC(=O)C6C5(CCC(C6)O)C)(C)O
• IUPAC Name: (1R,2S,6S,9S,10S,11S,14S,15S,18S,20S,23R,24S)-10,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one
• InChIKey: IQDIERHFZVCNRZ-YUYPDVIUSA-N
• INCHI: 1S/C27H43NO3/c1-15-4-7-25-27(3,31)21-6-5-17-18(20(21)14-28(25)13-15)11-22-19(17)12-24(30)23-10-16(29)8-9-26(22,23)2/h15-23,25,29,31H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-,22-,23+,25-,26+,27-/m0/s1
• Isómeros SMILES: C[C@H]1CC[C@H]2[C@@]([C@H]3CC[C@@H]4[C@H]([C@@H]3CN2C1)C[C@H]5[C@H]4CC(=O)[C@@H]6[C@@]5(CC[C@@H](C6)O)C)(C)O
• Peso molecular: 429.64
• Reaxy-Rn: 40284069
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=40284069&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Steroids and steroid derivatives
      • Subclass Steroidal alkaloids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Steroids and steroid derivatives
• Subclass: Steroidal alkaloids
• Intermediate Tree Nodes: Not available
• Direct Parent: Cerveratrum-type alkaloids
• Alternative Parents: Azasteroids and derivatives Quinolizidines Alkaloids and derivatives Piperidines Tertiary alcohols Trialkylamines Secondary alcohols Ketones Cyclic alcohols and derivatives 1,2-aminoalcohols Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Cerveratrum-type alkaloid - Azasteroid - Quinolizidine - Alkaloid or derivatives - Piperidine - Cyclic alcohol - Tertiary alcohol - Ketone - 1,2-aminoalcohol - Secondary alcohol - Tertiary amine - Tertiary aliphatic amine - Azacycle - Organoheterocyclic compound - Alcohol - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxide - Organic oxygen compound - Carbonyl group - Amine - Organic nitrogen compound - Aliphatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids.
• External Descriptors: Steroidal 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

Propiedades químicas y físicas

• Rotación específica [α]: -72° (C=0.5,MeOH)
• Punto de fusión (°C): 137 °C
• Peso molecular: 429.600 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 429.324 Da
• Monoisotopic Mass: 429.324 Da
• Topological Polar Surface Area: 60.800 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 755.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 12
• 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. Ma Xiaoyao, Liu Aina, Liu Wenjuan, Wang Zhihua, Chang Nianwei, Li Suyun, Li Jiansheng, Hou Yuanyuan, Bai Gang.  (2019)  Analyze and Identify Peiminine Target EGFR Improve Lung Function and Alleviate Pulmonary Fibrosis to Prevent Exacerbation of Chronic Obstructive Pulmonary Disease by Phosphoproteomics Analysis.  Frontiers in Pharmacology,      [PMID:31333459] [10.3389/fphar.2019.00737]

2. Ma Jingwei, Kan Hong, Ma Yinghui, Men Lihui, Pi Zifeng, Liu Zhiqiang, Liu Zhongying.  (2014)  Qualitative and quantitative analysis of drug interactions: Fritillary mediating the transport of alkaloids in caco-2 cells by p-glycoprotein.  CHEMICAL RESEARCH IN CHINESE UNIVERSITIES,  30  (5): (731-737).  [PMID:] [10.1007/s40242-014-4066-2]

3. Jiajin Xu, Zeyi Zhang, Hongtao Hu, Yaqin Yang, Chenghong Xiao, Luyi Xi, Jiahui Lu, Shasha Tian, Huajun Zhao.  (2024)  Synergistic antitumor effects of Peiminine and Doxorubicin on breast cancer through enhancing DNA damage via ZEB1.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:38432128] [10.1016/j.biopha.2024.116353]