Vernolepin

Vernolepin
Names
	Preferred IUPAC name (3aR,4S,5aR,9aR,9bR)-5a-Ethenyl-4-hydroxy-3,9-dimethylideneoctahydro-2H-furo[2,3-f][2]benzopyran-2,8(3H)-dione
	Other names Vernolepin
Identifiers
CAS Number	18542-37-5 ;
3D model (JSmol)	Interactive image ;
ChemSpider	390780 ;
KEGG	C09582 ;
PubChem CID	442322 ;
UNII	6640X1BVDX ;
CompTox Dashboard (EPA)	DTXSID6075146 ;
	InChI InChI=1S/C15H16O5/c1-4-15-5-9(16)10-7(2)14(18)20-12(10)11(15)8(3)13(17)19-6-15/h4,9-12,16H,1-3,5-6H2/t9-,10+,11+,12-,15+/m0/s1 Key: IFYQXAXVZGMFNW-MVIRXUPPSA-N; InChI=1/C15H16O5/c1-4-15-5-9(16)10-7(2)14(18)20-12(10)11(15)8(3)13(17)19-6-15/h4,9-12,16H,1-3,5-6H2/t9-,10+,11+,12-,15+/m0/s1 Key: IFYQXAXVZGMFNW-MVIRXUPPBC;
	SMILES C=C[C@]12C[C@@H]([C@@H]3[C@@H]([C@H]1C(=C)C(=O)OC2)OC(=O)C3=C)O;
Properties
Chemical formula	C15H16O5
Melting point	179 to 180 °C (354 to 356 °F; 452 to 453 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Last updated August 20, 2025

Vernolepin is a sesquiterpene lactone isolated from the dried fruit of Vernonia amygdalina . It shows platelet anti-aggregating properties^[2] and is also an irreversible DNA polymerase inhibitor,^[3] hence may have antitumor properties.

References

↑ Laekeman, G. M.; Mertens, J.; Totté, J.; Bult, H.; Vlietinck, A. J.; Herman, A. G. (1 March 1983). "Isolation and Pharmacological Characterization of Vernolepin". Journal of Natural Products. 46 (2): 161–169. Bibcode:1983JNAtP..46..161L. doi:10.1021/np50026a003. PMID 6410002.
↑ Laekeman, G. M.; Clerck, F.; Vlietinck, A. J.; Herman, A. G. (1 January 1985). "Vernolepin: An antiplatelet compound of natural origin". Naunyn-Schmiedeberg's Archives of Pharmacology. 331 (1): 108–113. doi:10.1007/BF00498859. PMID 3934564. S2CID 10373287.
↑ Clayden, Jonathan (2005). Organic chemistry (Reprinted (with corrections). ed.). Oxford [u.a.]: Oxford Univ. Press. pp. 238. ISBN 978-0-19-850346-0.

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[1] Laekeman, G. M.; Mertens, J.; Totté, J.; Bult, H.; Vlietinck, A. J.; Herman, A. G. (1 March 1983). "Isolation and Pharmacological Characterization of Vernolepin". Journal of Natural Products. 46 (2): 161–169. Bibcode:1983JNAtP..46..161L. doi:10.1021/np50026a003. PMID 6410002.

[2] Laekeman, G. M.; Clerck, F.; Vlietinck, A. J.; Herman, A. G. (1 January 1985). "Vernolepin: An antiplatelet compound of natural origin". Naunyn-Schmiedeberg's Archives of Pharmacology. 331 (1): 108–113. doi:10.1007/BF00498859. PMID 3934564. S2CID 10373287.

[3] Clayden, Jonathan (2005). Organic chemistry (Reprinted (with corrections). ed.). Oxford [u.a.]: Oxford Univ. Press. pp. 238. ISBN 978-0-19-850346-0.

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Names

Preferred IUPAC name (3aR,4S,5aR,9aR,9bR)-5a-Ethenyl-4-hydroxy-3,9-dimethylideneoctahydro-2H-furo[2,3-f][2]benzopyran-2,8(3H)-dione
Other names Vernolepin
Identifiers
CAS Number	18542-37-5 ^Y
3D model (JSmol)	Interactive image
ChemSpider	390780
KEGG	C09582
PubChem CID	442322
UNII	6640X1BVDX ^Y
CompTox Dashboard (EPA)	DTXSID6075146
InChI InChI=1S/C15H16O5/c1-4-15-5-9(16)10-7(2)14(18)20-12(10)11(15)8(3)13(17)19-6-15/h4,9-12,16H,1-3,5-6H2/t9-,10+,11+,12-,15+/m0/s1 Key: IFYQXAXVZGMFNW-MVIRXUPPSA-N InChI=1/C15H16O5/c1-4-15-5-9(16)10-7(2)14(18)20-12(10)11(15)8(3)13(17)19-6-15/h4,9-12,16H,1-3,5-6H2/t9-,10+,11+,12-,15+/m0/s1 Key: IFYQXAXVZGMFNW-MVIRXUPPBC
SMILES C=C[C@]12C[C@@H]([C@@H]3[C@@H]([C@H]1C(=C)C(=O)OC2)OC(=O)C3=C)O
Properties
Chemical formula	C₁₅H₁₆O₅
Melting point	179 to 180 °C (354 to 356 °F; 452 to 453 K)^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references