Scolymoside

Details

• Internal ID: 73853067-cf52-4f00-b752-5cf3a2833b66
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-9-20(33)22(35)24(37)26(38-9)42-25-23(36)21(34)18(8-28)41-27(25)39-11-5-14(31)19-15(32)7-16(40-17(19)6-11)10-2-3-12(29)13(30)4-10/h2-7,9,18,20-31,33-37H,8H2,1H3/t9-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
• InChI Key: SHPPXMGVUDNKLV-KMFFXDMSSA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.39
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

• Veronicastroside
• Scolymoside
• 25694-72-8
• Luteolin-7-O-rhamnoside
• Luteolin 7-O-neohesperidoside
• Luteoline-7-rhamnoglucoside
• LUTEOLIN-7-O-NEOHESPERIDOSIDE
• Luteolin 7-neohesperidoside
• ALJ2FB4ZDM
• CHEBI:31788
• CHEMBL452979
• DTXSID30180389
• 7-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-1-benzopyran-4-one
• 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside
• 7-(((2S,3R,4S,5S,6R)-4,5-DIHYDROXY-6-(HYDROXYMETHYL)-3-(((2S,3R,4R,5R,6S)-3,4,5-TRIHYDROXY-6-METHYLOXAN-2-YL)OXY)OXAN-2-YL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-4H-CHROMEN-4-ONE
• 7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one
• Honeysuckle glycosides
• UNII-ALJ2FB4ZDM
• 7-Neohesperidosylluteolin
• SCHEMBL2146638
• DTXCID90102880
• 7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one
• EX-A6773
• HY-N4136
• BDBM50242285
• 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-oxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-chromen-4-one
• AS-75312
• LUTEOLIN 7-O-beta-D-NEOHESPERIDOSIDE
• CS-0032185
• LUTEOLIN 7-O-.BETA.-D-NEOHESPERIDOSIDE
• Q3564258
• 4H-1-BENZOPYRAN-4-ONE, 7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-
• 7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-4H-1-BENZOPYRAN-4-ONE
• FLAVONE, 3',4',5,7-TETRAHYDROXY-, 7-(2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSIDE) (

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9189	91.89%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5645	56.45%
OATP1B1 inhibitior	+	0.9488	94.88%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5660	56.60%
P-glycoprotein inhibitior	-	0.7910	79.10%
P-glycoprotein substrate	-	0.5231	52.31%
CYP3A4 substrate	+	0.6167	61.67%
CYP2C9 substrate	-	0.6847	68.47%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.6943	69.43%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9241	92.41%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5236	52.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.6413	64.13%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9185	91.85%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7697	76.97%
Androgen receptor binding	+	0.5867	58.67%
Thyroid receptor binding	+	0.5707	57.07%
Glucocorticoid receptor binding	+	0.5408	54.08%
Aromatase binding	+	0.6252	62.52%
PPAR gamma	+	0.7852	78.52%
Honey bee toxicity	-	0.6392	63.92%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5750	57.50%
Fish aquatic toxicity	+	0.8289	82.89%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1929	P47989	Xanthine dehydrogenase	11900 nM	IC50	PMID: 9461655

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.74%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.71%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.01%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.83%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.28%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.38%	99.15%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.55%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.50%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.46%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.93%	86.92%
CHEMBL3194	P02766	Transthyretin	87.63%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.34%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.64%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.52%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.47%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.02%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.71%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.06%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.58%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.00%	95.89%

Plants that contains it

• Acacia aulacocarpa
• Achillea fragrantissima
• Achillea pannonica
• Anemonastrum flaccidum
• Ardisia neriifolia
• Artemisia argyi
• Artemisia montana
• Artemisia princeps
• Aspidosperma subincanum
• Asyneuma campanuloides
• Biebersteinia multifida
• Campanula persicifolia
• Carduus nutans
• Carex fraseriana
• Citrus maxima
• Cornulaca monacantha
• Cryptocarya aschersoniana
• Cynara cardunculus
• Daucus carota
• Eupatorium argentinum
• Garcinia madruno
• Gonocytisus angulatus
• Guatteria ucayalina
• Hedysarum setigerum
• Hylocomium splendens
• Juniperus brevifolia
• Launaea lanifera
• Lobelia nummularia
• Lonicera confusa
• Lonicera hypoglauca
• Lonicera japonica
• Lonicera macrantha
• Mentha × piperita
• Oenothera macrocarpa
• Panzerina lanata
• Peritassa compta
• Phlomis nissolii
• Phoenix loureiroi var. loureiroi
• Psiadia dentata
• Pteris cretica
• Reichardia tingitana
• Saussurea involucrata
• Scutellaria albida
• Setaria italica
• Tecoma stans
• Teucrium gnaphalodes
• Thymus membranaceus
• Trachelospermum asiaticum
• Trachycarpus fortunei
• Vellozia scoparia

Cross-Links

• PubChem: 5282152
• NPASS: NPC115674
• ChEMBL: CHEMBL452979
• LOTUS: LTS0219204
• wikiData: Q3564258