Cerbroside

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Basic information

CAS: 11005-70-2
Standard SMILES: CO[C@H]1[C@H](O)[C@H](C)O[C@H](O[C@H]2CC[C@]3(C)C4CC[C@]5(C)[C@@H](C6=CC(=O)OC6)CC[C@]5(O)C4CC[C@@H]3C2)[C@@H]1O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O
InChIKey: QWNHCYWCKDKDMK-UHFFFAOYSA-N
Molecular formula: C42H66O18
Average molar mass: 859 g/mol
Monoisotopic mass: 858.42491525

Overview

See also: Cerberoside (annotation moved to).

Names & identifiers

Preferred name: Cerbroside
IUPAC: 3-[(3S,5R,10S,13R,14S,17R)-14-hydroxy-3-[(2S,3R,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
English name: 3β-[[2-O-(6-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)-6-deoxy-3-O-methyl-α-L-glucopyranosyl]oxy]-14-hydroxy-5β,14β-card-20(22)-enolide
Molecular formula: C42H66O18
Molecular weight: 858.97

Names & synonyms

CerbrosideCerberosid [German]11005-70-2CerberosidBRN 1279318SCHEMBL294131655-beta-Card-20(22)-enolide, 3-beta-((O-beta-D-glucopyranosyl-(1-6)-O-beta-D-glucopyranosyl-(1-2)-6-deoxy-3-O-methyl-alpha-L-glucopyranosyl)oxy)-14-hydroxy-Cerberoside3β-[[2-O-(6-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)-6-deoxy-3-O-methyl-α-L-glucopyranosyl]oxy]-14-hydroxy-5β,14β-card-20(22)-enolideCard-20(22)-enolide, 3-[(O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→2)-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxy-, (3β,5β)-

Database identifiers

CAS: 11005-70-2
PubChem CID: 25437

Properties

Computed structural properties

XLogP: -1.6
Topological polar surface area: 273 Å²
Hydrogen bond donors: 9
Hydrogen bond acceptors: 18
Rotatable bonds: 10
Heavy atoms: 60
Formal charge: 0
Complexity: 1,570

Physicochemical properties

Melting point: 187.5 · 187.5-188.5 °C
Boiling point: 696.85 °C · 696.85°C (rough estimate)
Density: 1.1533 · 1.1533 (rough estimate)
refractive index: 1.624 · 1.6240 (estimate)
pka: 12.86 · 12.86±0.70(Predicted)

Related reactions

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Compound notes

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