ANAGALLOSIDE

Structure

2D structure of ANAGALLOSIDE
2D structure
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3D model

Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 102007423

Names and identifiers

Name

ANAGALLOSIDE

Also reported as

ANAGALLOSIDE B

IUPAC name

(2S,3R,4S,5S,6R)-2-(((2S,3R,4S,5S)-4-hydroxy-2-(((3S,4R,4aR,6aR,6bS,8R,8aS,12aR,12bS,14aR,14bR)-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyloctadecahydro-1H,9H-12b,8a-(epoxymethano)picen-3-yl)oxy)-5-(((2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-5-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-(((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

SMILES

C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC[C@@]45[C@]3(C[C@H]([C@@]6([C@H]4CC(CC6)(C)C)CO5)O)C)C)(C)CO)O[C@H]7[C@@H]([C@H]([C@H](CO7)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

General information

Molecular formula

C58H96O27

Molecular weight

1,225.38 g/mol

Monoisotopic mass

1,224.6139 Da

Classification

Pathway:
Superclass:
Class:
Glycoside:
Yes

Chemical classification: NPClassifier (Kim et al., 2021)

Plants with the compound

Plant Plant part Amount Reference
Lysimachia arvensis (L.) U.Manns & Anderb. - -
Shoji, N., Umeyama, A., Yoshikawa, K., Arihara, S. (1994). Structures of anagallosaponins 1-v and their companion substances from Anagallis arvensis L. Chem Pharm Bull, 42(9), 1750-1755 doi:10.1248/cpb.42.1750
Lysimachia arvensis (L.) U.Manns & Anderb. aerial parts -
Amoros, M., Girre, R.L. (1987). Structure of two antiviral triterpene saponins from Anagallis arvensis. Phytochemistry, 26(3), 787-791 doi:10.1016/s0031-9422(00)84787-1
Lysimachia arvensis (L.) U.Manns & Anderb. leaf -
Staron, T., Allard, C., Heitz, S., Billet, D. (1969). Purification and antifungic properties of a triterpene glycoside isolated from the stems and leaves of Anagallis arvensis var phoenicea. Phytiat Phytopharm, 18, 161
Veronica anagallis-aquatica L. subsp. anagallis-aquatica aerial parts -
Lahloub, M.F. (1992). A new iridoid glucoside from Veronica anagallis-aquatica var. anagalloides. Alexandria J Pharm Sci, 6(2), 134-135 doi:10.1055/s-2006-960437