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Loganic acid

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Loganic acid
Names
IUPAC name (1S,4aS,6S,7R,7aS)-1-(β-D-Glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopentapyran-4-carboxylic acid
Systematic IUPAC name (1S,4aS,6S,7R,7aS)-6-Hydroxy-7-methyl-1-{oxy}-1,4a,5,6,7,7a-hexahydrocyclopentapyran-4-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.040.781 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6+,8-,9+,10+,11+,12-,13+,15-,16-/m0/s1Key: JNNGEAWILNVFFD-CDJYTOATSA-N
  • InChI=1/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6+,8-,9+,10+,11+,12-,13+,15-,16-/m0/s1Key: JNNGEAWILNVFFD-CDJYTOATBB
SMILES
  • C1(C21(OC=C2C(=O)O)O3((((O3)CO)O)O)O)O
Properties
Chemical formula C16H24O10
Molar mass 376.358 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Loganic acid is an iridoid. Loganic acid is synthesized from 7-deoxyloganic acid by the enzyme 7-deoxyloganic acid hydroxylase (7-DLH). It is a substrate for the enzyme loganate O-methyltransferase for the production of loganin.

References

  1. Salim, Yu, Altarejos and De Luca (2013) Virus-induced gene silencing identifies Catharanthus roseus 7-deoxyloganic acid-7-hydroxylase, a step in iridoid and monoterpene indole alkaloid biosynthesis. The Plant Journal. 76(5). 754-765
  2. Miettinen, Dong, Navrot, Schneider, Burlat, et al. (2014) The seco-iridoid pathway from Catharanthus roseus. Nat Commun. 5(
  3. Dewick (2009) Medicinal Natural Products: A Biosynthetic Approach.


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