8-Epiloganic Acid
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Basic information
- CAS
82509-41-9- Standard SMILES
C[C@H]1[C@H]2[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C(C(=O)O)[C@H]2C[C@@H]1O- InChIKey
JNNGEAWILNVFFD-OZFVSFPVSA-N- Molecular formula
- C16H24O10
- Average molar mass
- 376.36 g/mol
- Monoisotopic mass
- 376.13694696
Overview
8-Epiloganic acid has been reported in Rehmannia glutinosa, Triaenophora rupestris, and other organisms with data available.
Names & identifiers
- Preferred name
- 8-Epiloganic Acid
- IUPAC
- (1S,4aS,6S,7S,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-carboxylic acid
- English name
- 8-EPILOGANIC ACID
- Molecular formula
- C16H24O10
- Molecular weight
- 376.36
Names & synonyms
8-Epiloganic acid82509-41-9(1S,4aS,6S,7S,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-carboxylic acidDTXSID40231816(1S,4aS,6S,7S,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-carboxylic acidRefChem:107085DTXCID701543078-epi-Loganic acid8-epi-loganin acid(1S,4aS,6S,7S,7aS)-6-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acidorb1217622orb1297154
Show more names
8-Phellodendric acid8-Epiloganic acid, 10 mM in DMSOLinaria,8 Epiloganic acid,Inhibitor,iridoid,8-Epiloganic acid,cymbalaria,glucoside,8Epiloganic acid,inhibit(1S)-1-(β-D-Glucopyranosyloxy)-1,4aα,5,6,7,7aα-hexahydro-6α-hydroxy-7β-methylcyclopenta[c]pyran-4-carboxylic acid(1S)-1α-(β-D-Glucopyranosyloxy)-1,4aα,5,6,7,7aα-hexahydro-6α-hydroxy-7β-methylcyclopenta[c]pyran-4-carboxylic acid
Properties
Computed structural propertiesFilling in
- XLogP
- -1.7
- Topological polar surface area
- 166 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 565
Physicochemical properties
- Melting point
- 138 · 138-139 °C
- Boiling point
- 646.3 · 646.3±55.0 °C(Predicted)
- Density
- 1.6 · 1.60±0.1 g/cm3(Predicted)
- form
- Solid
- pka
- 4.55 · 4.55±0.70(Predicted)
- color
- White to off-white
- InChIKey
- JNNGEAWILNVFFD-ARIMEKHGNA-N
- SMILES
- O([C@@]1([H])[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1OC=C(C(=O)O)[C@@]2([H])C[C@H](O)[C@@H](C)[C@@]12[H] |&1:1,3,4,6,8,13,20,23,25,27,r|
Chemistry & industry
Applications
Uses8-Epiloganic acid, an iridoid glucoside, can be found in Linaria cymbalaria (Scrophulariaceae)[1].
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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