(-)-Sweroside

Details

• Internal ID: dd655b8f-51e0-474c-ae08-de65851d85fc
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3S,4R,4aS)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one
• InChI: InChI=1S/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10-,11-,12+,13-,15+,16+/m1/s1
• InChI Key: VSJGJMKGNMDJCI-ZASXJUAOSA-N
• Popularity: 423 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₉
• Molecular Weight: 358.34 g/mol
• Exact Mass: 358.12638228 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: -0.90

Synonyms

• 14215-86-2
• (-)-Sweroside
• DTXSID70161955
• I3YG76417O
• (3S,4R,4aS)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one
• 1H,3H-Pyrano(3,4-c)pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-, (4aS-(4aalpha,5beta,6alpha))-
• 1,9-trans-9,5-cis-sweroside
• (3S,4R,4aS)-4-ethenyl-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-4,4a,5,6-tetrahydro-3H-pyrano(3,4-c)pyran-8-one
• RefChem:50458
• DTXCID4084446
• MFCD09954487
• CHEBI:80907
• UNII-I3YG76417O
• VSJGJMKGNMDJCI-ZASXJUAOSA-N
• 1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(ss-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-, (4aS,5R,6S)-; 1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(ss-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-, [4aS-(4aa,5ss,6a)]-; Sweroside (8CI); (-)-Sweroside; (4aS,5R,6S)-5-Ethenyl-6-(ss-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one
• Sweroside (Standard)
• SCHEMBL307117
• CHEMBL456137
• MEGxp0_000813
• orb1300159
• ACon0_001457
• ACon1_000233
• HY-N0806R
• 1H,3H-PYRANO(3,4-C)PYRAN-1-ONE, 5-ETHENYL-6-(.BETA.-D-GLUCOPYRANOSYLOXY)-4,4A,5,6-TETRAHYDRO-, (4AS-(4A.ALPHA.,5.BETA.,6.ALPHA.))-
• HY-N0806
• BDBM50279544
• s9072
• AKOS015960475
• Sweroside, >=95% (LC/MS-ELSD)
• CCG-268134
• FS73846
• NCGC00180755-01
• NCGC00180755-03
• AC-11215
• AC-35080
• AS-56077
• DA-58207
• CS-0009811
• NS00094766
• W0022
• C17071
• 142S862
• BRD-K31299876-001-01-5
• Q27151406
• (3S,4R,4aS)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4-vinyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one
• 1H,3H-PYRANO(3,4-C)PYRAN-1-ONE, 5-ETHENYL-6-(.BETA.-D-GLUCOPYRANOSYLOXY)-4,4A,5,6-TETRAHYDRO-, (4AS,5R,6S)-
• InChI=1/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10-,11-,12+,13-,15+,16+/m1/s1

2D Structure

ADMET Properties (via admetSAR 2)

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

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	94.95%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.63%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.24%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	88.22%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.91%	96.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.78%	83.57%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.38%	86.92%
CHEMBL2581	P07339	Cathepsin D	85.87%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.73%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	82.91%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.88%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.51%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.18%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.11%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.00%	95.83%

Plants that contains it

• Acacia aulacocarpa
• Alstonia rostrata
• Amsonia orientalis
• Anemonastrum flaccidum
• Anthocleista djalonensis
• Anthocleista nobilis
• Ardisia neriifolia
• Aspidosperma subincanum
• Bhesa paniculata
• Carapichea ipecacuanha
• Centaurium erythraea
• Cephalaria ambrosioides
• Chimarrhis turbinata
• Chione venosa
• Chironia purpurascens
• Citronella gongonha
• Cornus officinalis
• Cryptocarya aschersoniana
• Curtia tenuifolia
• Cyrtophyllum fragrans
• Desfontainia spinosa
• Dipsacus asperoides
• Dipsacus inermis
• Dipsacus laciniatus
• Eucnide bartonioides
• Eupatorium argentinum
• Euphorbia hirta
• Fagraea auriculata
• Fagraea gracilipes
• Flacourtia indica
• Garcinia madruno
• Gentiana algida
• Gentiana crassa subsp. rigescens
• Gentiana crassicaulis
• Gentiana dahurica
• Gentiana lutea
• Gentiana macrophylla
• Gentiana manshurica
• Gentiana olivieri
• Gentiana punctata
• Gentiana scabra
• Gentiana septemfida
• Gentiana sino-ornata
• Gentiana siphonantha
• Gentiana straminea
• Gentiana thunbergii
• Gentiana tibetica
• Gentiana triflora
• Gentiana verna
• Guatteria ucayalina
• Guettarda platypoda
• Halenia elliptica
• Helia alata
• Hemerocallis fulva
• Hydrangea chinensis
• Hydrangea macrophylla
• Juniperus brevifolia
• Lomelosia variifolia
• Lonicera angustifolia
• Lonicera caerulea
• Lonicera confusa
• Lonicera hypoglauca
• Lonicera japonica
• Lonicera macrantha
• Lonicera morrowii
• Lonicera quinquelocularis
• Mentzelia decapetala
• Nasa trianae
• Neonauclea sessilifolia
• Nyssa ogeche
• Ophiorrhiza japonica
• Ophiorrhiza kuroiwai
• Patrinia scabra
• Peritassa compta
• Potalia amara
• Psiadia dentata
• Schenkia spicata
• Simira williamsii
• Strychnos axillaris
• Strychnos spinosa
• Swertia arisanensis
• Swertia calycina
• Swertia chirayita
• Swertia franchetiana
• Swertia japonica
• Swertia pseudochinensis
• Swertia punicea
• Tabernaemontana cymosa
• Tripterospermum lanceolatum
• Tripterospermum trinervium

Cross-Links

• PubChem: 161036
• NPASS: NPC307699
• ChEMBL: CHEMBL456137
• LOTUS: LTS0014051
• wikiData: Q27151406