Venenatine

Venenatine
	File:Venenatine.svg
Names
	IUPAC name methyl (1R,15S,18R,19S,20S)-18-hydroxy-8-methoxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Identifiers
CAS Number	1055-75-0;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL4752387;
ChemSpider	65856;
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
E number	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
PubChem CID	73061;
CompTox Dashboard (EPA)	{{#property:P3117}};
	InChI InChI=1S/C22H28N2O4/c1-27-18-5-3-4-15-19(18)13-8-9-24-11-12-6-7-17(25)20(22(26)28-2)14(12)10-16(24)21(13)23-15/h3-5,12,14,16-17,20,23,25H,6-11H2,1-2H3/t12-,14+,16-,17-,20+/m1/s1 Key: WMMZYEBFJWWUJX-YCSGKXEJSA-N;
	SMILES COC1=CC=CC2=C1C3=C(N2)[C@H]4C[C@H]5[C@H](CC[C@H]([C@H]5C(=O)OC)O)CN4CC3;
Properties
Chemical formula	C22H28N2O4
Molar mass	384.5
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	176 mg/kg (mouse, intraperitoneal)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Venenatine is an indole alkaloid that was first isolated from Alstonia venenata in 1964.^[1] It is also found in A. macrophylla and A. scholaris.^[2] It appears to have antifungal properties^[3] and has been synthesized.^[4]^[5]

References

↑ Govindachari, T. R.; Viswanathan, N.; Pai, B. R.; Savitri, T. S. (January 1964). "Chemical constituents of Alstonia venenata R.Br". Tetrahedron Letters. 5 (16): 901–906. doi:10.1016/S0040-4039(00)90405-2.
↑ Tan, Maria Carmen S.; Carranza, Mary Stephanie S.; Linis, Virgilio C.; Malabed, Raymond S.; Oyong, Glenn G. (May 31, 2019). "Antioxidant, Cytotoxicity, and Antiophidian Potential of Alstonia macrophylla Bark". ACS Omega. 4 (5): 9488–9496. doi:10.1021/acsomega.9b00082. PMC 6648722 Check |pmc= value (help). PMID 31460040.
↑ Singh, U. P.; Sarma, B. K.; Mishra, P. K.; Ray, A. B. (2000). "Antifungal activity of venenatine, an indole alkaloid isolated from Alstonia venenata". Folia Microbiologica. 45 (2): 173–176. doi:10.1007/BF02817419. PMID 11271828.
↑ Lebold, Terry P.; Wood, Jessica L.; Deitch, Josh; Lodewyk, Michael W.; Tantillo, Dean J.; Sarpong, Richmond (2013). "A divergent approach to the synthesis of the yohimbinoid alkaloids venenatine and alstovenine". Nature Chemistry. 5 (2): 126–131. Bibcode:2013NatCh...5..126L. doi:10.1038/nchem.1528. PMC 3556932. PMID 23344433.
↑ Tang M, Lu H, Zu L (2024). "Collective total synthesis of stereoisomeric yohimbine alkaloids". Nature Communications. 15 (1). Bibcode:2024NatCo..15..941T. doi:10.1038/s41467-024-45140-2. PMC 10830567 Check |pmc= value (help). PMID 38296955 Check |pmid= value (help). Unknown parameter |article-number= ignored (help)

Bhattacharya, S. K.; Ray, A. B.; Dutta, S. C. (1975). "Psychopharmacological investigations of the 4-methoxyindole alkaloids of Alstonia venenata". Planta Medica. 27 (2): 164–170. Bibcode:1975PlMed..27..164B. doi:10.1055/s-0028-1097779. PMID 1121530.
Dhawan, B. N. (25 January 1995). "Research properties in natural products having CNS effects". Current Science. 68 (2): 202–204. JSTOR 24096503.
Magudeeswaran, Sivanandam; Poomani, Kumaradhas (February 2020). "Binding mechanism of spinosine and venenatine molecules with p300 HAT enzyme: Molecular screening, molecular dynamics and free‐energy analysis". Journal of Cellular Biochemistry. 121 (2): 1759–1777. doi:10.1002/jcb.29412.

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