2-[[5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: f48c2178-3ab5-4730-bf5b-b323a64f1252
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 2-[[5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=COC(C2C1C(C=C2CO)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=COC(C2C1C(C=C2CO)O)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2
• InChI Key: RJWJHRPNHPHBRN-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.33 g/mol
• Exact Mass: 346.12638228 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: -3.00

Synonyms

• NSC407293
• Rhimantin
• 2-[[5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• HMS3345J02
• AKOS037626766
• 5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl hexopyranoside
• LS-14438
• .Beta.-D-Glucopyranoside, 1,4a,5, 7a-tetrahydro-5-hydroxy-7- {(hydroxymethyl)cyclopenta[c]pyran-1-yl,} {[1S-(1.alpha.,4a.alpha.,5.alpha.,7a.alpha)]-}
• 2-[[5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	63.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.14%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.59%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.72%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	82.41%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.55%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.05%	97.36%

Plants that contains it

• Angelonia integerrima
• Antirrhinum majus
• Aragoa cundinamarcensis
• Aucuba japonica
• Aureolaria flava
• Cordylanthus kingii
• Crescentia cujete
• Eucommia ulmoides
• Euphrasia nemorosa
• Euphrasia salisburgensis
• Globularia bisnagarica
• Globularia nudicaulis
• Lathraea squamaria
• Melampyrum arvense
• Odontites vernus
• Parentucellia viscosa
• Pedicularis artselaeri
• Pedicularis chinensis
• Pedicularis condensata
• Pedicularis longiflora
• Pedicularis palustris
• Pedicularis rex
• Pedicularis striata
• Pedicularis verticillata
• Penstemon auriberbis
• Penstemon ovatus
• Penstemon serrulatus
• Plantago alpina
• Plantago hookeriana
• Plantago lanceolata
• Plantago major
• Plantago ovata
• Premna microphylla
• Scrophularia ningpoensis
• Scrophularia nodosa
• Stachys officinalis
• Utricularia vulgaris
• Verbascum georgicum
• Verbascum macrurum
• Verbascum phlomoides
• Verbascum pyroliforme subsp. dudleyanum
• Verbascum sinuatum
• Verbascum spinosum
• Verbascum thapsus
• Verbascum undulatum
• Veronica anagallis-aquatica
• Veronica austriaca
• Veronica bellidioides
• Veronica hederifolia
• Veronica longifolia
• Veronica orientalis
• Veronica serpyllifolia
• Veronica thomsonii
• Veronica turrilliana
• Vitex agnus-castus

Cross-Links

• PubChem: 348157
• LOTUS: LTS0183892
• wikiData: Q105238073