Sinomenine - Moligand™, ≥98% , CAS No.115-53-7

CAS: 115-53-7 Cat. No.: S302249 Molecular Weight: 329.39 EC Number: 204-094-6 PubChem CID: 5459308

GRADE & PURITY Moligand™, ≥98%

Synonyms

INYYVPJSBIVGPH-QHRIQVFBSA-N | Sinomenine, 0.3 mol chloroform of crystallization | (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one | Kukoline | NCGC00161641-04 | Spectrum4_001981

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Specifications

Synonyms

INYYVPJSBIVGPH-QHRIQVFBSA-N | Sinomenine, 0.3 mol chloroform of crystallization | (1R, 9S, 10S)-3-hydroxy-4, 12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01, 10.02, 7]heptadeca-2(7), 3, 5, 11-tetraen-13-one | Kukoline | NCGC00161641-04 | Spectrum4_001981

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Morphinan analog. μ-opioid receptor activator. Induces mast cell degranulation. Releases histamine and suppresses proinflammatory cytokine production. Shows anti-inflammatory, antinociceoptive and antineuropathic analgesic effects in vivo.

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

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

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504763823
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763823
• Canonical Smiles: CN1CCC23CC(=O)C(=CC2C1CC4=C3C(=C(C=C4)OC)O)OC
• IUPAC Name: (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
• InChIKey: INYYVPJSBIVGPH-QHRIQVFBSA-N
• INCHI: 1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1
• Isomeric SMILES: CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC
• PubChem CID: 5459308
• Molecular Weight: 329.39

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Morphinans

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Morphinans
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Morphinans
• Alternative Parents: Phenanthrenes and derivatives Benzazocines Isoquinolones and derivatives Tetralins Anisoles Cyclohexenones Aralkylamines Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids Piperidines Trialkylamines Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Morphinan - Phenanthrene - Benzazocine - Isoquinolone - Tetralin - Anisole - Alkyl aryl ether - 1-hydroxy-4-unsubstituted benzenoid - Cyclohexenone - Aralkylamine - Piperidine - Benzenoid - Ketone - Tertiary amine - Tertiary aliphatic amine - Cyclic ketone - Azacycle - Ether - Organoheterocyclic compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Carbonyl group - Amine - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
• External Descriptors: Isoquinoline 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

Associated Targets(Human)

ACHE Tclin Acetylcholinesterase (18204 Activities)

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TNF Tclin TNF-alpha (1897 Activities)

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CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

Discover Target: CDK2

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MCF7 (126967 Activities)

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KB (17409 Activities)

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MDA-MB-231 (73002 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Entamoeba histolytica (2676 Activities)

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Plasmodium falciparum (966862 Activities)

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Rattus norvegicus (775804 Activities)

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RAW264.7 (28094 Activities)

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NIH3T3 (5395 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light sensitive;Moisture sensitive
• Melt Point(°C): 180 °C (dec.)(lit.)
• Molecular Weight: 329.400 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 329.163 Da
• Monoisotopic Mass: 329.163 Da
• Topological Polar Surface Area: 59.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 562.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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

References

1. Ji Chen, Peng Guo, Xinxin Liu, Huizhi Liao, Kemin Chen, Yuxia Wang, Jie Qin, Fengrui Yang.  (2023)  Sinomenine alleviates diabetic peripheral neuropathic pain through inhibition of the inositol-requiring enzyme 1 alpha–X-box binding protein 1 pathway by downregulating prostaglandin-endoperoxide synthase 2.  Journal of Diabetes Investigation,  14  (3): (364-375).  [PMID:36692011] [10.1111/jdi.13938]

2. Zhou Zhiyong, Qiu Nanqing, Ou Yuntao, Wei Qianqian, Tang Wenting, Zheng Mingcong, Xing Yaluan, Li Jie-Jia, Ling Yong, Li Junxu, Zhu Qing.  (2021)  N-Demethylsinomenine, an active metabolite of sinomenine, attenuates chronic neuropathic and inflammatory pain in mice.  Scientific Reports,  11  (1): (1-9).  [PMID:33927244] [10.1038/s41598-021-88521-z]

3. Yuntao Ou, Man Su, Yong Ling, Qianqian Wei, Fei Pan, Jiejia Li, Jun-Xu Li, Qing Zhu.  (2018)  Anti-allodynic effects of N-demethylsinomenine, an active metabolite of sinomenine, in a mouse model of postoperative pain.  EUROPEAN JOURNAL OF PHARMACOLOGY,      [PMID:29408089] [10.1016/j.ejphar.2018.01.044]

4. Qing Wang, Ling Tong, Lin Yao, Peng Zhang, Li Xu.  (2016)  Fingerprinting of traditional Chinese medicines on the C18-Diol mixed-mode column in online or offline two-dimensional liquid chromatography on the single column modes.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:27031576] [10.1016/j.jpba.2016.03.033]

5. Qing Zhu, Yuehua Sun, Lina Mao, Chengpeng Liu, Bo Jiang, Wei Zhang, Jun-Xu Li.  (2016)  Antinociceptive effects of sinomenine in a rat model of postoperative pain.  BRITISH JOURNAL OF PHARMACOLOGY,  173  (10): (1693-1702).  [PMID:26915970] [10.1111/bph.13470]

6. Qing Wang, Yao Long, Lin Yao, Li Xu, Zhi-Guo Shi, Lanying Xu.  (2015)  Preparation, characterization and application of a reversed phase liquid chromatography/hydrophilic interaction chromatography mixed-mode C18-DTT stationary phase.  TALANTA,      [PMID:26695288] [10.1016/j.talanta.2015.09.009]

7. Qing Wang, Zhi-Yuan Luo, Mao Ye, Yu-Zhuo Wang, Li Xu, Zhi-guo Shi, Lanying Xu.  (2015)  Preparation, chromatographic evaluation and application of adenosine 5′-monophosphate modified ZrO2/SiO2 stationary phase in hydrophilic interaction chromatography.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:25627970] [10.1016/j.chroma.2015.01.017]

8. Zhu Qing, Sun Yuehua, Zhu Jie, Fang Tian, Zhang Wei, Li Jun-Xu.  (2014)  Antinociceptive effects of sinomenine in a rat model of neuropathic pain.  Scientific Reports,  4  (1): (1-5).  [PMID:25434829] [10.1038/srep07270]