Deoxyloganic acid
Basic information
- CAS
22487-36-1- Standard SMILES
C[C@H]1CC[C@@H]2C(C(=O)O)=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]21- InChIKey
DSXFHNSGLYXPNG-YDYVGBNJSA-N- Molecular formula
- C16H24O9
- Average molar mass
- 360.36 g/mol
- Monoisotopic mass
- 360.14203234
Overview
7-deoxyloganic acid is a cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1 and 7 by beta-D-glucosyloxy and methyl groups respectively (the 1S,4aS,7S,7aR-diatereomer). It has a role as a plant metabolite. It is a beta-D-glucoside, a cyclopentapyran, an iridoid monoterpenoid, a monosaccharide derivative, a monoterpene glycoside and an alpha,beta-unsaturated monocarboxylic acid. It is functionally related to a 7-deoxyloganetic acid. It is a conjugate acid of a 7-deoxyloganate.
Names & identifiers
- Preferred name
- Deoxyloganic acid
- IUPAC
- (1S,4aS,7S,7aR)-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
- (1R,2S,6S,9S)-9-methyl-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]non-4-ene-5-carboxylic acid
- Molecular formula
- C16H24O9
- Molecular weight
- 360.36
Names & synonyms
7-Deoxyloganic acidDeoxyloganic acid22487-36-1SZ67QWR9D3CHEBI:2260DTXSID40945163(1S,4aS,7S,7aR)-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(1S,4aS,7S,7aR)-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:106025DTXCID101373489Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-, (1S-(1alpha,4aalpha,7alpha,7aalpha))-(1R,2S,6S,9S)-9-METHYL-2-[(2S,3R,4S,5R,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY-3-OXABICYCLO[4.3.0]NON-4-ENE-5-CARBOXYLIC ACID
Show more names
Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-, (1S,4aS,7S,7aR)-
(1S,4aS,7S,7aR)-1-(beta-D-glucopyranosyloxy)-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acidBISDEOXYDIHYDROMONOTROPEINC11636bis-desoxydihydromonotropeinorb1991476SCHEMBL20572414AKOS040735291Q19596786
Properties
Computed structural properties
- XLogP
- -0.4
- Topological polar surface area
- 146 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 536
Physicochemical properties
- Melting point
- 88 · 88-90 °C
- Boiling point
- 597.2 · 597.2±50.0 °C(Predicted)
- Density
- 1.52 · 1.52±0.1 g/cm3(Predicted)
- pka
- 4.65 · 4.65±0.60(Predicted)
- FDA UNII
- 67 QWR9D3 · SZ67QWR9D3
Chemistry & industry
Additional notes
DefinitionChEBI: 7-deoxyloganic acid is a cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1 and 7 by beta-D-glucosyloxy and methyl groups respectively (the 1S,4aS,7S,7aR-diatereomer). It has a role as a plant metabolite. It is a beta-D-glucoside, a cyclopentapyran, a monoterpene glycoside, a monosaccharide derivative, an iridoid monoterpenoid and an alpha,beta-unsaturated monocarboxylic acid. It is functionally related to a 7-deoxyloganetic acid. It is a conjugate acid of a 7-deoxyloganate.
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