Geoside

Details

• Internal ID: 8422a541-c4f5-461c-81c7-7a298285b7ad
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-(2-methoxy-4-prop-2-enylphenoxy)-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)CC=C)OC2C(C(C(C(O2)COC3C(C(C(CO3)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CC=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O)O)O)O
• InChI: InChI=1S/C21H30O11/c1-3-4-10-5-6-12(13(7-10)28-2)31-21-19(27)17(25)16(24)14(32-21)9-30-20-18(26)15(23)11(22)8-29-20/h3,5-7,11,14-27H,1,4,8-9H2,2H3/t11-,14+,15-,16+,17-,18+,19+,20-,21+/m0/s1
• InChI Key: FSCNUJMKSQHQSY-KJYATZHYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₁₁
• Molecular Weight: 458.50 g/mol
• Exact Mass: 458.17881177 g/mol
• Topological Polar Surface Area (TPSA): 168.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.93
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• 585-90-0
• Gein
• (2S,3R,4S,5S,6R)-2-(4-Allyl-2-methoxyphenoxy)-6-((((2S,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol
• Eugenyl vicianoside
• HY-N6903
• AKOS040740792
• CS-0100515

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7336	73.36%
Caco-2	-	0.8455	84.55%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6056	60.56%
OATP2B1 inhibitior	-	0.8614	86.14%
OATP1B1 inhibitior	+	0.8715	87.15%
OATP1B3 inhibitior	+	0.9597	95.97%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5933	59.33%
P-glycoprotein inhibitior	-	0.7805	78.05%
P-glycoprotein substrate	-	0.6239	62.39%
CYP3A4 substrate	+	0.6102	61.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7559	75.59%
CYP3A4 inhibition	-	0.8503	85.03%
CYP2C9 inhibition	-	0.8967	89.67%
CYP2C19 inhibition	-	0.8607	86.07%
CYP2D6 inhibition	-	0.8679	86.79%
CYP1A2 inhibition	-	0.8876	88.76%
CYP2C8 inhibition	+	0.6676	66.76%
CYP inhibitory promiscuity	-	0.8491	84.91%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6770	67.70%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9653	96.53%
Skin irritation	-	0.8157	81.57%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7130	71.30%
Micronuclear	-	0.5826	58.26%
Hepatotoxicity	-	0.6958	69.58%
skin sensitisation	-	0.7741	77.41%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.9531	95.31%
Acute Oral Toxicity (c)	III	0.7658	76.58%
Estrogen receptor binding	+	0.6522	65.22%
Androgen receptor binding	-	0.7863	78.63%
Thyroid receptor binding	+	0.5416	54.16%
Glucocorticoid receptor binding	-	0.5378	53.78%
Aromatase binding	+	0.6363	63.63%
PPAR gamma	+	0.7304	73.04%
Honey bee toxicity	-	0.7550	75.50%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8318	83.18%

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	98.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.22%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.08%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.34%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.16%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.59%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	88.49%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.63%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.30%	92.94%
CHEMBL4208	P20618	Proteasome component C5	84.99%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.78%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.62%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.95%	95.89%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	82.46%	85.49%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.09%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	81.93%	94.73%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	81.86%	97.88%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.83%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	81.43%	95.93%
CHEMBL5957	P21589	5'-nucleotidase	81.25%	97.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.80%	95.56%

Plants that contains it

• Adenopeltis serrata
• Arisaema erubescens
• Bituminaria bituminosa
• Centaurea seridis
• Chrozophora tinctoria
• Cneorum pulverulentum
• Dalbergia stipulacea
• Delphinium ajacis
• Elaeagnus commutata
• Eucalyptus flocktoniae
• Flindersia brayleyana
• Heracleum sphondylium
• Jungermannia obovata
• Kummerowia striata
• Mascarenhasia arborescens
• Meconopsis napaulensis
• Merremia umbellata
• Millettia conraui
• Palafoxia rosea
• Pedicularis condensata
• Perityle vaseyi
• Phoebe formosana
• Piloselloides hirsuta
• Plectranthus garckeanus
• Porella swartziana
• Quercus mongolica
• Rheum webbianum
• Rhodiola rosea
• Salacia chinensis
• Salvia coulteri
• Sapindus mukorossi
• Satureja cuneifolia
• Senecio flavus
• Sida cordifolia
• Solanum sisymbriifolium
• Thymbra spicata
• Turraeanthus mannii

Cross-Links

• PubChem: 25087713
• NPASS: NPC33103
• LOTUS: LTS0170752
• wikiData: Q105000572