Leucoside

Details

• Internal ID: 34f06201-5f6f-4c49-b03e-1d3f14dfcd3a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)CO)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)CO)O)O)O)O)O
• InChI: InChI=1S/C26H28O15/c27-7-15-18(33)20(35)24(41-25-21(36)17(32)13(31)8-37-25)26(39-15)40-23-19(34)16-12(30)5-11(29)6-14(16)38-22(23)9-1-3-10(28)4-2-9/h1-6,13,15,17-18,20-21,24-33,35-36H,7-8H2/t13-,15-,17+,18-,20+,21-,24-,25+,26+/m1/s1
• InChI Key: RXAXTTGJEMODPY-CJNLAGEVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₅
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.14282018 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.78
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

• 27661-51-4
• 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• Kaempferol 3-sambubioside
• Kaempferol 3-O-sambubioside
• Kaemoferol 5-Xyl(1,2)Glc
• CHEMBL446574
• CHEBI:189496
• HY-N2186
• Leucoside, >=90% (LC/MS-UV)
• AKOS032946051
• MS-30413
• CS-0019494
• 3-(((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5110	51.10%
Caco-2	-	0.9300	93.00%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4988	49.88%
OATP2B1 inhibitior	-	0.5552	55.52%
OATP1B1 inhibitior	+	0.8752	87.52%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7851	78.51%
P-glycoprotein inhibitior	-	0.5858	58.58%
P-glycoprotein substrate	-	0.5511	55.11%
CYP3A4 substrate	+	0.6683	66.83%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9373	93.73%
CYP2C9 inhibition	-	0.9644	96.44%
CYP2C19 inhibition	-	0.9395	93.95%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	-	0.9304	93.04%
CYP2C8 inhibition	+	0.7896	78.96%
CYP inhibitory promiscuity	-	0.8779	87.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6882	68.82%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.8908	89.08%
Skin irritation	-	0.8205	82.05%
Skin corrosion	-	0.9667	96.67%
Ames mutagenesis	+	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4063	40.63%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6547	65.47%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9162	91.62%
Acute Oral Toxicity (c)	III	0.4508	45.08%
Estrogen receptor binding	+	0.8312	83.12%
Androgen receptor binding	+	0.6975	69.75%
Thyroid receptor binding	+	0.5509	55.09%
Glucocorticoid receptor binding	+	0.5623	56.23%
Aromatase binding	+	0.6770	67.70%
PPAR gamma	+	0.7875	78.75%
Honey bee toxicity	-	0.7186	71.86%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.7253	72.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.67%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.06%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.46%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.62%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.21%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	93.65%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.65%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.90%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.11%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.79%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.67%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.01%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.25%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.24%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.14%	95.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.58%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.19%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	84.58%	94.75%
CHEMBL3194	P02766	Transthyretin	84.26%	90.71%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	82.70%	80.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.22%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.11%	90.00%

Plants that contains it

• Actinidia arguta
• Aesculus chinensis
• Aesculus hippocastanum
• Albertisia papuana
• Artemisia biennis
• Astragalus asper
• Aulacomnium androgynum
• Cosmos pringlei
• Dahlstedtia araripensis
• Daphnopsis macrophylla
• Delphinium grandiflorum var. fangshanense
• Derris trifoliata
• Dioscorea althaeoides
• Drimia maritima
• Erythrina sacleuxii
• Ficus salicifolia
• Gardneria nutans
• Glycyrrhiza lepidota
• Harungana madagascariensis
• Lafoensia glyptocarpa
• Lonchocarpus parviflorus
• Magnolia sprengeri
• Melaleuca ericifolia
• Osteophloeum platyspermum
• Phaseolus vulgaris
• Pteridium esculentum
• Rhodiola rosea
• Sesamoides interrupta
• Spiranthes australis
• Taraxacum bicorne
• Uncaria tomentosa
• Valeriana fedtschenkoi
• Vasconcellea pubescens

Cross-Links

• PubChem: 44566720
• NPASS: NPC304741
• LOTUS: LTS0251907
• wikiData: Q104399732