Cyclovirobuxine - analytical standard , CAS No.860-79-7

CAS: 860-79-7 Cat. No.: C117989 Molecular Weight: 402.364 EC Number: 632-924-0

GRADE & PURITY Analytical standard

Synonyms

AKOS015896107 | CYCLOVIROBUXINE D [WHO-DD] | 4,4,14-Trimethyl-3alpha,20-bis(methylamino)-9,19-cyclo-5alpha-pregnan-16-ol | SCHEMBL3385409 | Cyclovirobuxine D | NCGC00346606-01 | NCGC00346606-02 | NSC 91722 | s2402 | Cyclovirobuxin D (Bebuxine) | HUANWEIHU

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

An anti-atrial fibrillating agent

Specifications

Synonyms

AKOS015896107 | CYCLOVIROBUXINE D [WHO-DD] | 4, 4, 14-Trimethyl-3alpha, 20-bis(methylamino)-9, 19-cyclo-5alpha-pregnan-16-ol | SCHEMBL3385409 | Cyclovirobuxine D | NCGC00346606-01 | NCGC00346606-02 | NSC 91722 | s2402 | Cyclovirobuxin D (Bebuxine) | HUANWEIHU

Specifications & Purity

analytical standard

Biochemical and Physiological Mechanisms

Cyclovirobuxine D is an anti-atrial fibrillating agent. It induces release of endothelial nitric oxide.

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Grade

Analytical standard

Names and Identifiers

• Canonical Smiles: CC(C1C(CC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)NC)C)C)O)NC
• IUPAC Name: (1S,3R,6S,8R,11S,12S,14R,15S,16R)-7,7,12,16-tetramethyl-6-(methylamino)-15-[(1S)-1-(methylamino)ethyl]pentacyclo[9.7.0.01,3.03,8.012,16]octadecan-14-ol
• InChIKey: GMNAPBAUIVITMI-ABNIRSKTSA-N
• INCHI: 1S/C26H46N2O/c1-16(27-6)21-17(29)14-24(5)19-9-8-18-22(2,3)20(28-7)10-11-25(18)15-26(19,25)13-12-23(21,24)4/h16-21,27-29H,8-15H2,1-7H3/t16-,17+,18-,19-,20-,21-,23+,24-,25+,26-/m0/s1
• Isomeric SMILES: C[C@@H]([C@H]1[C@@H](C[C@@]2([C@@]1(CC[C@]34[C@H]2CC[C@@H]5[C@]3(C4)CC[C@@H](C5(C)C)NC)C)C)O)NC
• Molecular Weight: 402.364
• Reaxy-Rn: 47748950
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=47748950&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Triterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Triterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Triterpenoids
• Alternative Parents: Buxus alkaloids 16-alpha-hydroxysteroids Azasteroids and derivatives Alkaloids and derivatives Secondary alcohols Cyclic alcohols and derivatives Dialkylamines Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Triterpenoid - 22-azasteroid - 9(beta),19-cyclo-4,4-14(alpha)-trimethyl-5(alpha)-pregnane-skeleton - Steroidal alkaloid - Hydroxysteroid - 16-alpha-hydroxysteroid - 16-hydroxysteroid - Steroid - Azasteroid - Alkaloid or derivatives - Cyclic alcohol - Secondary alcohol - Secondary amine - Secondary aliphatic amine - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Alcohol - Organic oxygen compound - Organic nitrogen compound - Amine - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
• External Descriptors: Not available

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(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Mechanisms of Action

Chemical and Physical Properties

• Refractive Index: 1.55
• Boil Point(°C): 495.7 °C
• Melt Point(°C): 219-222°C
• Molecular Weight: 402.700 g/mol
• XLogP3: 5.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 402.361 Da
• Monoisotopic Mass: 402.361 Da
• Topological Polar Surface Area: 44.300 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 692.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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. Ting Xue, Yaodong Chen, Jia Xu, Weiqin Du, Pengzhou Kong, Xinri Zhang.  (2023)  Cyclovirobuxine D inhibits growth and progression of non‑small cell lung cancer cells by suppressing the KIF11‑CDC25C‑CDK1‑CyclinB1 G2/M phase transition regulatory network and the NFκB/JNK signaling pathway.  INTERNATIONAL JOURNAL OF ONCOLOGY,  62  (5): (1-21).  [PMID:36929198] [10.3892/ijo.2023.5505]

2. Fengqi Jiang, Yaodong Chen, Shuo Ren, Zizhuo Li, Kan  Sun, Yanwei Xing, Yuekun Zhu, Daxun Piao.  (2020)  Cyclovirobuxine D inhibits colorectal cancer tumorigenesis via the CTHRC1‑AKT/ERK‑Snail signaling pathway.  INTERNATIONAL JOURNAL OF ONCOLOGY,  57  (1): (183-196).  [PMID:32319595] [10.3892/ijo.2020.5038]

3. Jiuwei Zhang, Yaodong Chen, Jing Lin, Ruimei Jia, Tingting An, Tianxiu Dong, Yu Zhang, Xiuhua Yang.  (2020)  Cyclovirobuxine D Exerts Anticancer Effects by Suppressing the EGFR-FAK-AKT/ERK1/2-Slug Signaling Pathway in Human Hepatocellular Carcinoma.  DNA AND CELL BIOLOGY,  39  (3): (355-367).  [PMID:31913706] [10.1089/dna.2019.4990]

4. Jiang Xinru, Li Hongdan, Liu Yang.  (2024)  Cyclovirobuxine D inhibits hepatocellular carcinoma growth by inducing ferroptosis of hepatocellular carcinoma cells.  Discover Oncology,  15  (1): (1-11).  [PMID:38563866] [10.1007/s12672-024-00940-2]

5. Jinku Guo, Yingfeng Cao, Kaipen Jin, Bing Liu, Wei Wang, Chen Chen, Jun Xie, Ankai Xu.  (2026)  Cyclovirobuxine D suppresses cancer stemness in osteosarcoma with implication of the noncanonical NF-kappaB pathway.  Frontiers in Pharmacology,      [PMID:] [10.3389/fphar.2026.1746984]