General Characteristics
2D structure
NatID 1
Common Name Dehydroleucodine
Molecular Formula C15H16O3
Chemical Class Lactones > Gamma butyrolactones
Molecular Weight 244.110 g/mol
Other names dehydroleucodine 36150-07-9 Dehydroleucodin

 

Representations
Smiles C=C1C(=O)O[C@H]2[C@H]1CCC(C)=C1C(=O)C=C(C)[C@@H]12
Inchi InChI=1S/C15H16O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,10,13-14H,3-5H2,1-2H3/t10-,13-,14-/m0/s1
Inchi Key SKNVIAFTENCNGB-BPNCWPANSA-N
3D Structure

 

Calculated Properties
clogP 2.34
TPSA 43.37
HBD 0
HBA 3
Rotatable Bonds 0
Aromatic Rings 0
Heavy Atoms 18
Aromatic Carbocycles 0
Aromatic Heterocycles 0
Number of NO 3

 

Experiments
EID Source Semisynthetic? Confidence level References
9031 Gaillardia megapotamica var. radiata No Very High Jimenez-Ortiz, V., Brengio, S. D., Giordano, O., Tonn, C., Sánchez, M., Burgos, M. H., & Sosa, M. A. (2005). THE TRYPANOCIDAL EFFECT OF SESQUITERPENE LACTONES HELENALIN AND MEXICANIN ON CULTURED EPIMASTIGOTES. Journal of Parasitology, 91(1), 170–174. https://doi.org/10.1645/ge-3373
9110 Artemisia douglasiana No Very High Giordano, O. S., Pestchanker, M. J., Guerreiro, E., Saad, J. R., Enriz, R. D., Rodriguez, A. M., Jauregui, E. A., Guzman, J., Maria, A. O. M., & Wendel, G. H. (1992). Structure-activity relationship in the gastric cytoprotective effect of several sesquiterpene lactones. Journal of Medicinal Chemistry, 35(13), 2452–2458. https://doi.org/10.1021/jm00091a013 Guardia, T., Guzman, J. A., Pestchanker, M. J., Guerreiro, E., & Giordano, O. S. (1994). Mucus Synthesis and Sulfhydryl Groups in Cytoprotection Mediated by Dehydroleucodine, a Sesquiterpene Lactone. Journal of Natural Products, 57(4), 507–509. https://doi.org/10.1021/np50106a010 Giordano, O. S., Guerreiro, E., Pestchanker, M. J., Guzman, J., Pastor, D., & Guardia, T. (1990). The Gastric Cytoprotective Effect of Several Sesquiterpene Lactones. Journal of Natural Products, 53(4), 803–809. https://doi.org/10.1021/np50070a004 Wendel, G. H., Maria, A. O. M., Domínguez, N. S., Mohamed, F., Scardapane, L., Guzmán, J. A., Giordano, O., & Pelzer, L. E. (2007). Intrarectal Dehydroleucodine Suppresses Trinitrobenzene Sulfonic Acid–Induced Colitis in Rats, A Model for Inflammatory Bowel Disease. Pharmaceutical Biology, 45(4), 316–323. https://doi.org/10.1080/13880200701212866
9347 Xanthium orientale No Unknown Penissi, A. B., Vera, M. E., Mariani, M. L., Rudolph, M. I., Ceñal, J. P., de Rosas, J. C., Fogal, T. H., Tonn, C. E., Favier, L. S., Giordano, O. S., & Piezzi, R. S. (2009). Novel anti-ulcer α,β-unsaturated lactones inhibit compound 48/80-induced mast cell degranulation. European Journal of Pharmacology, 612(1–3), 122–130. https://doi.org/10.1016/j.ejphar.2009.03.052
9712 Gaillardia megapotamica var. scabiosoides No Unknown MARIA, A. O., WENDEL, G. H., GUARDIA, T., GUZMAN, J. A., PESTCHANKER, M. J., GUERREIRO, E., & GIORDANO, O. S. (1995). Gastric Cytoprotective Activity of 2-Cyclopenten-1-one and Related Compounds. Biological and Pharmaceutical Bulletin, 18(12), 1784–1786. https://doi.org/10.1248/bpb.18.1784
9767 Ambrosia scabra No Unknown Sülsen, V. P., & Martino, V. S. (2018). Sesquiterpene Lactones. Springer Cham, https://doi.org/10.1007/978-3-319-78274-4

 

Bioassay ID NPASS ID Target Activity type Activity