INTEGERRIMINE

Structure

2D structure of INTEGERRIMINE
2D structure
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3D model

Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 5281733

Names and identifiers

Name

INTEGERRIMINE

IUPAC name

(5R,6R,9a1R,14aR,E)-3-ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione

SMILES

C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C

General information

Molecular formula

C18H25NO5

Molecular weight

335.40 g/mol

Monoisotopic mass

335.1733 Da

Classification

Pathway:
Superclass:
Class:
Glycoside:
No

Chemical classification: NPClassifier (Kim et al., 2021)

Plants with the compound

Plant Plant part Amount Reference
Petasites hybridus (L.) G.Gaertn., B.Mey. & Scherb. subsp. hybridus - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Petasites hybridus (L.) G.Gaertn., B.Mey. & Scherb. subsp. hybridus leaf -
Wichtl, M. 1984. Teedrogen. Ein Handbuch fur Apotheker und Arzte. Wissenschaftliche Verlagsgesellscharft. mbH Stuttgart. 393 pp.
Petasites hybridus (L.) G.Gaertn., B.Mey. & Scherb. subsp. hybridus root -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Senecio inaequidens DC. - -
Bicchi, C., Rubiolo, P., Frattini, C., Sandra, P., David, F. (1991). Off-line supercritical fluid extraction and capillary gas chromatography of pyrrolizidine alkaloids in Senecio species. J Nat Prod, 54(4), 941-945 doi:10.1021/np50076a003
Senecio inaequidens DC. aerial parts -
Rubiolo, P., Pieters, L., Calomme, M., Bicchi, C., Vlietinck, A., Vandenberghe, D. (1992). Mutagenicity of pyrrolizidine alkaloids in the salmonella typhimurium/mammalian microsome system. Mutat Res, 281(2), 143-147 doi:10.1016/0165-7992(92)90050-r
Senecio vulgaris L. subsp. vulgaris - -
Chizzola, R. (1994). Rapid sample preparation technique for the determination of pyrrolizidine alkaloids in plant extracts. J Chromatogr A, 668(2), 427-433 doi:10.1016/0021-9673(94)80135-5
Senecio vulgaris L. subsp. vulgaris aerial parts -
Luthy, J., Heim, T.H., Schlatter, C.H. (1983). Transfer of [3-h]pyrrolizidine alkaloids from Senecio vulgaris L. and metabolites into rat milk and tissues. Toxicol Lett, 17(3/4), 283-288 doi:10.1016/0378-4274(83)90239-4
Senecio vulgaris L. subsp. vulgaris leaf -
Ehmke, A., Proksch, P., Witte, L., Hartmann, T., Isman, M.B. (1989). Fate of ingested pyrrolizidine alkaloid n-oxide in the grasshopper Melanoplus sanguinipes. Naturwissenschaften, 76(1), 27-29 doi:10.1007/bf00368308