Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-, methyl ester, (1S,4aS,7S,7aR)-
Basic information
- CAS
26660-57-1- Standard SMILES
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1CC[C@@H]2C- InChIKey
KMHXLGLJTQHEIM-OUEWTLASSA-N- Molecular formula
- C17H26O9
- Average molar mass
- 374.4 g/mol
- Monoisotopic mass
- 374.1576824
Overview
7-deoxyloganin is a beta-D-glucoside, a methyl ester and an alpha,beta-unsaturated carboxylic ester. It is functionally related to a loganin.
Names & identifiers
- Preferred name
- Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-, methyl ester, (1S,4aS,7S,7aR)-
- IUPAC
- methyl (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-carboxylate
- English name
- Deoxyloganin
- Molecular formula
- C17H26O9
- Molecular weight
- 374.38
Names & synonyms
Deoxyloganin7-Deoxyloganin26660-57-1CHEBI:18370DTXSID10331539methyl (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-carboxylateCyclopenta[c]pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-, methyl ester, (1S,4aS,7S,7aR)-Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-, methyl ester, (1S,4aS,7S,7aR)-methyl (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-carboxylateRefChem:919421DTXCID10282633methyl (1S,4aS,7S,7aR)-1-(beta-D-glucopyranosyloxy)-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Show more names
(1S)-1α-(β-D-Glucopyranosyloxy)-7α-methyl-1,4aα,5,6,7,7aα-hexahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester(1S)-1α-(β-D-Glucopyranosyloxy)-1,4aα,5,6,7,7aα-hexahydro-7α-methylcyclopenta[c]pyran-4-carboxylic acid methyl ester
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 135 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 5
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 550
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
Chemistry & industry
Applications
Uses7-Deoxyloganin serves as a biosynthetic precursor of Loganin (HY-N0512). 7-Deoxyloganin undergoes hydroxylation catalyzed by 7-deoxyloganin 7-hydroxylase, a cytochrome P450-dependent monooxygenase, to produce Loganin[1].
Additional notes
DefinitionChEBI: 7-deoxyloganin is an alpha,beta-unsaturated carboxylic ester, a methyl ester and a beta-D-glucoside. It is functionally related to a loganin.
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