Clethroidoside B

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Grundinformationen

CAS: 1335200-65-1
Standard-SMILES: CC(=O)OC[C@@]12[C@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6OC[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]1CC(C)(C)[C@@H](O)[C@@H]2O
InChIKey: WJBKGNOXYGTIHU-FTWMTZRVSA-N
Summenformel: C49H80O20
Durchschnittliche Molmasse: 989,1 g/mol
Monoisotopische Masse: 988,52429494

Überblick

Clethroidoside B is a triterpenoid saponin that is barringtogenol C which is acetylated at position 28 and attached to a beta-D-glucopyranosyl-(12)-[beta-D-glucopyranosyl-(14)]-alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. It has been isolated from the aerial parts of Lysimachia clethroides. It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a triol, an acetate ester, a triterpenoid saponin and a trisaccharide derivative. It is functionally related to a barringtogenol C. It derives from a hydride of an oleanane.

Namen und Bezeichner

Bevorzugter Name: Clethroidoside B
IUPAC: [(3R,4R,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-3,4,5-trihydroxy-10-[(2S,3R,4S,5S)-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-4a-yl]methyl acetate

Namen und Synonyme

Clethroidoside BCHEBI:69602DTXSID8011005481335200-65-1Q27137945(3beta,16alpha,21beta,22alpha)-3-{[beta-D-glucopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->4)]-alpha-L-arabinopyranosyl]oxy}-16,21,22-trihydroxyolean-12-en-28-yl acetate3-O-beta-D-glucopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->4)]-alpha-L-arabinopyranosyl-28-acetyl-3beta,16alpha,21beta,22alpha,28-pentahydroxyolean-12-eneI+/--L-Arabinopyranoside, (3I(2),16I+/-,21I(2),22I+/-)-28-(acetyloxy)-16,21,22-trihydroxyolean-12-en-3-yl O-I(2)-D-glucopyranosyl-(1a2)-O-[I(2)-D-glucopyranosyl-(1a4)]-

Datenbank-Bezeichner

CAS: 1335200-65-1
PubChem CID: 56601654
DTXSID: DTXSID801100548
ChEBI: CHEBI:69602
Nikkaji: J2.999.492G

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -0,1
Polarare Oberfläche (TPSA): 324 Å²
H-Brücken-Donoren: 12
H-Brücken-Akzeptoren: 20
Frei drehbare Bindungen: 11
Schwere Atome: 69
Formalladung: 0
Komplexität: 1.880

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