Icariside B2

Details

• Internal ID: 8fde968b-9504-4099-847e-a391ab1a8b95
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (E)-4-[(1S,4S,6R)-2,2,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-oxabicyclo[4.1.0]heptan-1-yl]but-3-en-2-one
• SMILES (Canonical): CC(=O)C=CC12C(CC(CC1(O2)C)OC3C(C(C(C(O3)CO)O)O)O)(C)C
• SMILES (Isomeric): CC(=O)/C=C/[C@]12[C@](O1)(C[C@H](CC2(C)C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C
• InChI: InChI=1S/C19H30O8/c1-10(21)5-6-19-17(2,3)7-11(8-18(19,4)27-19)25-16-15(24)14(23)13(22)12(9-20)26-16/h5-6,11-16,20,22-24H,7-9H2,1-4H3/b6-5+/t11-,12+,13+,14-,15+,16+,18+,19-/m0/s1
• InChI Key: RZPOXAOUEYNXNO-VLSJDARNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₀O₈
• Molecular Weight: 386.40 g/mol
• Exact Mass: 386.19406791 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.34
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• CHEMBL2392399
• (1R)-1beta,5,5-Trimethyl-3beta-(beta-D-glucopyranosyloxy)-6beta-(3-oxo-1-butenyl)-7-oxabicyclo[4.1.0]heptane
• 108906-51-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5955	59.55%
Caco-2	-	0.6705	67.05%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7260	72.60%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8852	88.52%
OATP1B3 inhibitior	+	0.8883	88.83%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8304	83.04%
P-glycoprotein inhibitior	-	0.7595	75.95%
P-glycoprotein substrate	-	0.9020	90.20%
CYP3A4 substrate	+	0.6180	61.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.8947	89.47%
CYP2C9 inhibition	-	0.8379	83.79%
CYP2C19 inhibition	-	0.8688	86.88%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	-	0.8656	86.56%
CYP2C8 inhibition	-	0.8361	83.61%
CYP inhibitory promiscuity	-	0.9378	93.78%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6872	68.72%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9644	96.44%
Skin irritation	-	0.7855	78.55%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.6223	62.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.7162	71.62%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.7733	77.33%
skin sensitisation	-	0.8293	82.93%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.5573	55.73%
Acute Oral Toxicity (c)	III	0.5162	51.62%
Estrogen receptor binding	+	0.6636	66.36%
Androgen receptor binding	+	0.6179	61.79%
Thyroid receptor binding	+	0.7238	72.38%
Glucocorticoid receptor binding	+	0.7080	70.80%
Aromatase binding	+	0.6326	63.26%
PPAR gamma	+	0.5705	57.05%
Honey bee toxicity	-	0.7310	73.10%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.8601	86.01%

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	98.30%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.41%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.27%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.37%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.66%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.46%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.70%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.51%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.24%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.66%	96.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.54%	91.24%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.54%	89.34%
CHEMBL2581	P07339	Cathepsin D	80.60%	98.95%

Plants that contains it

• Acanthophyllum elatius
• Acer carpinifolium
• Boronia coerulescens
• Campanula medium
• Chamaecyparis pisifera
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium sagittatum
• Euphorbia helioscopia
• Galium rubioides
• Helichrysum lepidissimum
• Helleborus multifidus
• Heptapleurum divaricatum
• Hopea utilis
• Hymenoxys ambigens var. floribunda
• Hypericum revolutum
• Ilex chinensis
• Iryanthera coriacea
• Leuzea centauroides
• Litsea salicifolia
• Melochia tomentosa
• Mesembryanthemum expansum
• Nelumbo nucifera
• Nepeta italica subsp. cadmea
• Ornithogalum nutans
• Osmorhiza aristata
• Psychotria serpens
• Pycnandra acuminata
• Rubia oncotricha
• Saussurea cordifolia
• Scurrula atropurpurea
• Staphylea bumalda
• Stipa robusta
• Succisa pratensis
• Tabebuia angustata
• Tithonia rotundifolia
• Veratrum lobelianum

Cross-Links

• PubChem: 10385469
• NPASS: NPC167983
• LOTUS: LTS0079463
• wikiData: Q105248520