CH₃CH₃

Bacoside A

Chemistry

122 atoms · Coordinates generated from the structure by CORINA (NCI CACTUS) — PubChem has no conformer for this one.
Formula
C41H68O13
Molar mass
769.0 g/mol
IUPAC name
(5R,8R,9S,10S,13R,14R,17S)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-10-(hydroxymethyl)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta[a]phenanthren-16-one
InChIKey
LKCTWIIDXXXXAR-CYGHALRTSA-N

Chemistry from PubChem CID 92043183.

Also known as

  • 11028-00-5
  • (5R,8R,9S,10S,13R,14R,17S)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-10-(hydroxymethyl)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta[a]phenanthren-16-one
  • (5R,8R,9S,10S,13R,14R,17S)-3-((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-((2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl)oxy-10-(hydroxymethyl)-17-((2S)-2-hydroxy-6-methylhept-5-en-2-yl)-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta(a)phenanthren-16-one
  • RefChem:116280
  • DTXSID901053841
  • Gynostemma Pentaphyllum P.E. Gypenoside
  • Bacoside-A
  • Bacoside A (Mixture)

Stereoisomers

6 distinct stereoisomers are registered for this structure. This area's record is the racemate — the mixture, which is normally the form encountered.

  • (3R,5R,8R,9R,10R,13S,14S,17R)-3-[(2S,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-10-(hydroxymethyl)-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta[a]phenanthren-16-one CID 124909784
  • (3R,5R,8R,9R,10R,13S,14S,17R)-3-[(2S,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-10-(hydroxymethyl)-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta[a]phenanthren-16-one CID 124909785
  • (3R,5R,8R,9R,10R,13S,14S,17R)-3-[(2S,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-10-(hydroxymethyl)-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta[a]phenanthren-16-one CID 124909786
  • (3R,5R,8R,9R,10R,13S,14S,17R)-3-[(2S,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-10-(hydroxymethyl)-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta[a]phenanthren-16-one CID 124909787
  • (3R,5R,8R,9S,10S,13R,14R,17S)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-10-(hydroxymethyl)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta[a]phenanthren-16-one CID 125121512
  • (3S,5R,8R,9S,10S,13R,14R,17S)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-10-(hydroxymethyl)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta[a]phenanthren-16-one CID 125121513
  • BACOSIDE A(SH);3-[(O-alpha-L-Arabinopyranosyl-beta-D-glucopyranosyl)oxy]-19,20-dihydroxydammar-24-en-16-one;Dammar-24-en-16-one,3-[(O-R-Larabinopyranosyl-a-D-glucopyranosyl)oxy]-19,-20-dihydroxy- mixture CID 53398644

Photographs

sample Bacopa monnieri (brahmi, water hyssop), the source plant of bacoside A: a creeping succulent herb of wet ground with paddle-shaped fleshy leaves and small white five-lobed flowers. The whole aerial herb is the part used.
Bacopa monnieri (brahmi, water hyssop), the source plant of bacoside A: a creeping succulent herb of wet ground with paddle-shaped fleshy leaves and small white five-lobed flowers. The whole aerial herb is the part used.
Forest & Kim Starr ·CC BY
sample Close view of Bacopa monnieri: thick spoon-shaped leaves in opposite pairs and a solitary white flower with a pale throat. Leaf and stem are the parts used in extracts standardized to bacosides.
Close view of Bacopa monnieri: thick spoon-shaped leaves in opposite pairs and a solitary white flower with a pale throat. Leaf and stem are the parts used in extracts standardized to bacosides.
Krzysztof Ziarnek, Kenraiz ·CC BY-SA
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