Home › Entities › Methyl 2-(hexopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate › (-)-secologanin

(-)-secologanin

chemical compound
Class type of: Methyl 2-(hexopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate Q1531155

Facts

10 properties
Instance of
type of chemical entity
Subclass of
Methyl 2-(hexopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate
Part of
(-)-secologanin metabolic process, (-)-secologanin catabolic process, (-)-secologanin biosynthetic process, strictosidine synthase activity, deacetylisoipecoside synthase activity, deacetylipecoside synthase activity, secologanin synthase activity
Canonical SMILES
COC(=O)C1=COC(C(C1CC=O)C=C)OC2C(C(C(C(O2)CO)O)O)O
Chemical formula
C₁₇H₂₄O₁₀
Found in taxon
Catharanthus roseus, Lonicera japonica, Cruckshanksia verticillata, Gentiana verna, Lonicera caerulea, Acicarpha tribuloides, Adina pilulifera, Sinoadina racemosa, Cinchona calisaya, Cruckshanksia pumila, Curtia tenuifolia, Desfontainia fulgens, Desfontainia spinosa, Dipsacus asper, Guettarda speciosa, Hydrangea macrophylla, Lippia graveolens, Lippia origanoides, Lonicera dioica, Lonicera korolkowii, Lonicera morrowii, Lonicera periclymenum, Lonicera tatarica, Strychnos nux-vomica, Symphoricarpos orbiculatus, Weigela coraeensis, Weigela florida, Weigela japonica, Weigela middendorffiana, Strychnos spinosa, Dipsacus inermis, Pterocephalus perennis
Has part(s)
carbon, oxygen, hydrogen
Isomeric SMILES
COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC=O)C=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Mass
+388.137
Stereoisomer of
methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate, methyl (2S,3R,4R)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate, methyl (2R,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate, methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
🏷️ Also known as
en methyl (2S,3R,4S)-4-(formylmethyl)-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate en (-)-secologanin en secologanin cs sekologanin es Secologanina fa سکولوگانین fi sekologaniini fr Sécologanine ja セコロガニン ro Secologanină ru секологанин zh 断马钱子苷
🔖 Identifiers · 24
CAS Registry Number
19351-63-4
ChEBI ID
18002
ChEMBL ID
CHEMBL1235867
ChemSpider ID
141670
DSSTOX compound identifier
DTXCID001369483
DSSTox substance ID
DTXSID30941033
Freebase ID
/m/0gvr5rf
Human Metabolome Database ID
HMDB0304482
InChI
InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1
InChIKey
CSKKDSFETGLMSB-NRZPKYKESA-N
KEGG ID
C01852
KNApSAcK ID
C00003098
Show all 24 identifiers +12
LIPID MAPS ID
LMPR0102070002
Microsoft Academic ID (discontinued)
2777989177
NSC number
640525
PDB ligand ID
SCG
PDB structure ID
3U5Y, 2FPC
Probes And Drugs ID
PD088458
PubChem CID
161276
Reaxys registry number
1441446
SPLASH
splash10-0aor-1900000000-773184210e8bb7a9052b
SureChEMBL ID
431171
UNII
NK7B26K93T
UniChem compound ID
648146

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🔗 Connections
Found in taxon 28
Catharanthus roseus, Strychnos nux-vomica, Hydrangea macrophylla, Lonicera japonica, Lonicera caerulea, Lonicera periclymenum, Gentiana verna, Lonicera tatarica +20 more
Has part(s) 3
hydrogen, oxygen, carbon
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Summary

(-)-secologanin is a type of chemical entity[1].

Key Facts

  • Canonical SMILES: COC(=O)C1=COC(C(C1CC=O)C=C)OC2C(C(C(C(O2)CO)O)O)O[2]
  • Chemical formula: C₁₇H₂₄O₁₀[3]
  • Subclass of: Methyl 2-(hexopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate[4]
  • Part of: (-)-secologanin metabolic process[5], (-)-secologanin catabolic process[6], (-)-secologanin biosynthetic process[7], strictosidine synthase activity[8], deacetylisoipecoside synthase activity[9], deacetylipecoside synthase activity[10], secologanin synthase activity[11]
  • Has part(s): carbon[12], oxygen[13], hydrogen[14]
  • Found in taxon: Catharanthus roseus[15], Lonicera japonica[16], Cruckshanksia verticillata[17], Gentiana verna[18], Lonicera caerulea[19], Acicarpha tribuloides[20], Adina pilulifera[21], Sinoadina racemosa[22], Cinchona calisaya[23], Cruckshanksia pumila[24], Curtia tenuifolia[25], Desfontainia fulgens[26], Desfontainia spinosa[27], Dipsacus asper[28]
  • Isomeric SMILES: COC(=O)C1=COC@HO[C@H]2C@@HOC@HO[C@H]2C@@HO">[29]
  • Mass: 388.137 dalton[30]
  • Stereoisomer of: methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate[31], methyl (2S,3R,4R)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate[32], methyl (2R,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate[33], methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate[34]

References

Programmatic citations — every numbered marker resolves to a verifiable graph row below.

Direct Wikidata claims

  1. [2] ↑ . PubChem. Retrieved . wikidata.org.
  2. [3] ↑ . PubChem. Retrieved . wikidata.org.
  3. [4] ↑ . wikidata.org.
  4. [5] ↑ . Gene Ontology release 2019-11-16. wikidata.org.
  5. [6] ↑ . Gene Ontology release 2019-11-16. wikidata.org.
  6. [7] ↑ . Gene Ontology release 2019-11-16. wikidata.org.
  7. [8] ↑ . Gene Ontology release 2020-05-02. wikidata.org.
  8. [9] ↑ . Gene Ontology release 2020-05-02. wikidata.org.
  9. [10] ↑ . Gene Ontology release 2020-05-02. wikidata.org.
  10. [11] ↑ . Gene Ontology release 2020-05-02. wikidata.org.
  11. [12] ↑ . wikidata.org.
  12. [13] ↑ . wikidata.org.
  13. [14] ↑ . wikidata.org.
  14. [15] ↑ . Accumulation of loganin and secologanin in vacuoles from suspension cultured Catharanthus roseus cells. wikidata.org.
  15. [16] ↑ . Isolation of Secoiridoid Artifacts from Lonicera japonica. wikidata.org.
  16. [17] ↑ . Iridoids of Cruckshanksia verticillata and their Chemosystematic importance. wikidata.org.
  17. [18] ↑ . Secologanin and Derivatives from Gentiana verna. wikidata.org.
  18. [19] ↑ . Caeruleosides A and B, bis-iridoid glucosides from Lonicera caerulea. wikidata.org.
  19. [20] ↑ . Phytochemical and pharmacological studies on medicinal herb Acicarpha tribuloides. wikidata.org.
  20. [21] ↑ . Studies on monoterpene glucosides and related natural products. XLII. On the possibility of the intermediacy of 10-hydroxyloganin in the biosynthesis of secologanin.. wikidata.org.
  21. [22] ↑ . Six Secoiridoid Glucosides from Jasminum polyanthum.. wikidata.org.
  22. [23] ↑ . Control and biological implications of alkaloid synthesis inCinchona seedlings. wikidata.org.
  23. [24] ↑ . Iridoids from Cruckshanksia pumila (Rubiaceae). wikidata.org.
  24. [25] ↑ . Iridoid glucosides from Curtia tenuifolia. wikidata.org.
  25. [26] ↑ . Iridoids, iridoid-triterpenoid congeners and lignans from Desfontainia spinosa. wikidata.org.
  26. [27] ↑ . Iridoids, iridoid-triterpenoid congeners and lignans from Desfontainia spinosa. wikidata.org.
  27. [28] ↑ . Acylated triterpene glycoside from roots of Dipsacus asper. wikidata.org.
  28. [29] ↑ . PubChem. Retrieved . wikidata.org.
  29. [30] ↑ . PubChem. Retrieved . wikidata.org.
  30. [31] ↑ . wikidata.org.
  31. [32] ↑ . wikidata.org.
  32. [33] ↑ . wikidata.org.
  33. [34] ↑ . wikidata.org.

Class ancestry

  1. [1] ↑ . Wikidata. wikidata.org.

📑 Cite this page

Use these citations when quoting this entity in research, articles, AI prompts, or wherever provenance matters. We aggregate Wikidata + Wikipedia + authoritative open-data sources; the stitched, scored, cross-referenced view is what 4ort.xyz contributes.

APA 4ort.xyz Knowledge Graph. (2026). (-)-secologanin. Retrieved November 8, 2026, from https://4ort.xyz/entity/secologanin
MLA “(-)-secologanin.” 4ort.xyz Knowledge Graph, 4ort.xyz, 8 Nov. 2026, https://4ort.xyz/entity/secologanin.
BibTeX @misc{4ortxyz_secologanin_2026, author = {{4ort.xyz Knowledge Graph}}, title = {{(-)-secologanin}}, year = {2026}, url = {https://4ort.xyz/entity/secologanin}, note = {Accessed: 2026-11-08}}
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Edit History

Rolling log of changes to this entity's Wikidata record. Values shown reflect the current state of each edited property — follow the history link to see the precise diff for any edit.

  1. 27w ago · Shuaib-bot bot · 2026-05-02 view diff on Wikidata ↗
    Mass → 388.137 dalton
    Subclass of → Methyl 2-(hexopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihyd
    Found in taxon → Catharanthus roseus, Lonicera japonica, Cruckshanksia verticillata +1
    Instance of → type of chemical entity
    + 3 other properties edited (see Wikidata diff for full list)
    "Changed [ur] labels, descriptions, aliases and claims"
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