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Loganin information


Loganin
Names
IUPAC name
Methyl (1S,4aS,6S,7R,7aS)-1-(β-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Systematic IUPAC name
Methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Other names
Loganoside
Identifiers
CAS Number
  • 18524-94-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15771
ChemSpider
  • 79111
ECHA InfoCard 100.038.529 Edit this at Wikidata
EC Number
  • 242-398-0
KEGG
  • C01433
PubChem CID
  • 87691
UNII
  • H7WJ16Q93C checkY
CompTox Dashboard (EPA)
  • DTXSID60939948 Edit this at Wikidata
InChI
  • InChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1
    Key: AMBQHHVBBHTQBF-UOUCRYGSSA-N
  • InChI=1/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1
    Key: AMBQHHVBBHTQBF-UOUCRYGSBL
SMILES
  • C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
Properties
Chemical formula
 C17H26O10
Molar mass 390.385 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Loganin is one of the best-known of the iridoid glycosides. It is named for the Loganiaceae, having first been isolated from the seeds of a member of that plant family, namely those of Strychnos nux-vomica. It also occurs in Alstonia boonei (Apocynaceae),[1] a medicinal tree of West Africa and in the medicinal/entheogenic shrub Desfontainia spinosa (Columelliaceae) native to Central America and South America.

  1. ^ Adotey, J. P.; Adukpo, G. E.; Opoku-Boahen, Y.; Armah, F. A. (2012). "A Review of the Ethnobotany and Pharmacological Importance of Alstonia boonei De Wild (Apocynaceae)". ISRN Pharmacology. 2012: 587160. doi:10.5402/2012/587160. PMC 3413980. PMID 22900200.

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Loganin

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Loganin is one of the best-known of the iridoid glycosides. It is named for the Loganiaceae, having first been isolated from the seeds of a member of...

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Loganiaceae

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alkaloids such as those found in Strychnos. Glycosides are also present as loganin in Strychnos. Earlier treatments of the family have included up to 29 genera...

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Secologanin synthase

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reaction loganin + NADPH + H+ + O2 ⇌ {\displaystyle \rightleftharpoons } secologanin + NADP+ + 2 H2O The 4 substrates of this enzyme are loganin, NADPH...

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Secologanin

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the entire secologanin biosynthetic pathway. Secologanin is formed from loganin through the action of the enzyme secologanin synthase. Secologanin is then...

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Glycoside

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contain an iridoid group; e.g. aucubin, geniposidic acid, theviridoside, loganin, catalpol. As the name contains the prefix thio-, these compounds contain...

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Triosteum

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A–C, naucledal, secologanin dimethyl acetal, grandifloroside, sweroside, loganin, vogeloside and (E)-aldosecologanin ) have recently been isolated from...

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Loganic acid

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substrate for the enzyme loganate O-methyltransferase for the production of loganin. Salim, Yu, Altarejos and De Luca (2013) Virus-induced gene silencing identifies...

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Desfontainia

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quantity is the pentacyclic triterpene acid ursolic acid. Also present are loganin and secoxyloganin, compounds related to secologanin a molecule involved...

Word Count : 2087

Listooder

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Rademon Church Listooder Missionary Hall "Placenames Database of Ireland". Loganin. Retrieved 10 February 2014. Davies, Rosalind. "Kilmore Parish townlands"...

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Sarracenin

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the Okefenokee swamp region Sarracenin is believed to be derived from loganin, with either morronoside or secologanin serving as intermediates in the...

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