Icariside E4

Details

• Internal ID: 17eac517-04ae-4add-888b-e81cb76374dd
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[4-[(2R,3S)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(C=C(C=C2)C3C(C4=C(O3)C(=CC(=C4)CCCO)OC)CO)OC)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C=C(C=C2)[C@H]3[C@@H](C4=C(O3)C(=CC(=C4)CCCO)OC)CO)OC)O)O)O
• InChI: InChI=1S/C26H34O10/c1-13-21(29)22(30)23(31)26(34-13)35-18-7-6-15(11-19(18)32-2)24-17(12-28)16-9-14(5-4-8-27)10-20(33-3)25(16)36-24/h6-7,9-11,13,17,21-24,26-31H,4-5,8,12H2,1-3H3/t13-,17+,21-,22+,23+,24-,26-/m0/s1
• InChI Key: FYWCDZKQBWSMDD-YGYBHAICSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₀
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.21519728 g/mol
• Topological Polar Surface Area (TPSA): 147.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

• 126253-42-7
• CHEBI:68965
• (2S,3R,4R,5R,6S)-2-[4-[(2R,3S)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]-6-methyloxane-3,4,5-triol
• alpha-L-Mannopyranoside, 4-[(2R,3S)-2,3-dihydro-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2-benzofuranyl]-2-methoxyphenyl 6-deoxy-
• CHEMBL1923075
• DTXSID101317861
• AKOS040762654
• Q27137317
• (2R)-2,3-Dihydro-2beta-[3-methoxy-4-(alpha-L-rhamnopyranosyloxy)phenyl]-3alpha-(hydroxymethyl)-7-methoxybenzofuran-5-(1-propanol)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7219	72.19%
Caco-2	-	0.7702	77.02%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6611	66.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8178	81.78%
OATP1B3 inhibitior	+	0.9411	94.11%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8158	81.58%
P-glycoprotein inhibitior	-	0.4784	47.84%
P-glycoprotein substrate	+	0.5665	56.65%
CYP3A4 substrate	+	0.6498	64.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7646	76.46%
CYP3A4 inhibition	-	0.9207	92.07%
CYP2C9 inhibition	-	0.8683	86.83%
CYP2C19 inhibition	-	0.8738	87.38%
CYP2D6 inhibition	-	0.9051	90.51%
CYP1A2 inhibition	-	0.8404	84.04%
CYP2C8 inhibition	+	0.8050	80.50%
CYP inhibitory promiscuity	-	0.7408	74.08%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5860	58.60%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9471	94.71%
Skin irritation	-	0.8279	82.79%
Skin corrosion	-	0.9505	95.05%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7751	77.51%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8839	88.39%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7546	75.46%
Acute Oral Toxicity (c)	III	0.7256	72.56%
Estrogen receptor binding	+	0.8088	80.88%
Androgen receptor binding	+	0.5509	55.09%
Thyroid receptor binding	+	0.6229	62.29%
Glucocorticoid receptor binding	+	0.6142	61.42%
Aromatase binding	-	0.5094	50.94%
PPAR gamma	+	0.5564	55.64%
Honey bee toxicity	-	0.8290	82.90%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7355	73.55%
Fish aquatic toxicity	-	0.5157	51.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.26%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.97%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.57%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.52%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.91%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.85%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.57%	91.11%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.04%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	88.09%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	87.47%	91.49%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.21%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.61%	95.56%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	84.31%	97.31%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.65%	94.00%
CHEMBL2535	P11166	Glucose transporter	83.31%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.30%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.22%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.63%	89.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.52%	94.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.78%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.61%	92.94%

Plants that contains it

• Acer saccharum
• Austrocedrus chilensis
• Juniperus communis
• Nymphaea odorata
• Pedicularis torta

Cross-Links

• PubChem: 21589939
• NPASS: NPC79429
• LOTUS: LTS0014118
• wikiData: Q27137317