(1S,3R,6S,7S,8R,11S,12S,16R)-7,12,16-Trimethyl-15-[(1S)-1-[(2S)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid
Basic information
- CAS
124962-06-7- Standard SMILES
CC1=CC[C@@H]([C@@H](C)C2CC[C@@]3(C)[C@@H]4CC[C@H]5[C@](C)(C(=O)O)[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)CC[C@@]56C[C@@]46CC[C@]23C)OC1=O- InChIKey
CJHYXUPCGHKJOO-OMWWMXIRSA-N- Molecular formula
- C36H54O10
- Average molar mass
- 646.8 g/mol
- Monoisotopic mass
- 646.37169792
Overview
(1S,3R,6S,7S,8R,11S,12S,16R)-7,12,16-Trimethyl-15-[(1S)-1-[(2S)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid is a triterpenoid saponin.
Names & identifiers
- Preferred name
- (1S,3R,6S,7S,8R,11S,12S,16R)-7,12,16-Trimethyl-15-[(1S)-1-[(2S)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid
- IUPAC
- (1S,3R,6S,7S,8R,11S,12S,16R)-7,12,16-trimethyl-15-[(1S)-1-[(2S)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid
- English name
- (20S,22S)-3β-(β-D-Glucopyranosyloxy)-22-hydroxy-9β,19-cyclolanost-24-ene-26,29-dioic acid δ-lactone
- Molecular formula
- C36H54O10
- Molecular weight
- 646.82
Names & synonyms
(1S,3R,6S,7S,8R,11S,12S,16R)-7,12,16-Trimethyl-15-[(1S)-1-[(2S)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acidAC1L9BW2DTXSID20331661CHEBI:182963C08920(17xi,22S)-3beta-(beta-D-Glucopyranosyloxy)-26-oxo-9beta-22,26-epoxy-9,19-cyclolanost-24-en-28-oic acidAbrusoside A(20S,22S)-3β-(β-D-Glucopyranosyloxy)-22-hydroxy-9β,19-cyclolanost-24-ene-26,29-dioic acid δ-lactone9,19-Cyclolanost-24-ene-26,28-dioic acid, 3-(β-D-glucopyranosyloxy)-22-hydroxy-, δ-lactone, (3β,4α,22S)-
Database identifiers
- CAS
124962-06-7- PubChem CID
- 441902
- DTXSID
DTXSID20331661- ChEBI
CHEBI:182963
Properties
Computed structural properties
- XLogP
- 5.3
- Topological polar surface area
- 163 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 6
- Heavy atoms
- 46
- Formal charge
- 0
- Complexity
- 1,300
Physicochemical properties
- Boiling point
- 813.6 · 813.6±65.0 °C(Predicted)
- Density
- 1.33 · 1.33±0.1 g/cm3(Predicted)
- pka
- 4.41 · 4.41±0.70(Predicted)
Chemistry & industry
Applications
UsesAbrusoside A is a highly sweet triterpene glycoside isolated from the leaves of Abrus precatorius. Abrusoside A has potential application value as a sweetener[1].
Additional notes
DefinitionChEBI: A triterpenoid saponin that is (22S,24Z)-3beta-hydroxy-26-oxo-22,26-epoxy-9beta,19-cyclolanost-24-en-28-oic acid having a beta-D-glucosyl residue attached at position 3 via a glycosidic bond.
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