Gastrodioside

Details

• Internal ID: f9ded733-bc4d-4c32-aa4e-46221b10b37a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(4-hydroxyphenyl)methoxymethyl]phenoxy]oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1COCC2=CC=C(C=C2)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1COCC2=CC=C(C=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C20H24O8/c21-9-16-17(23)18(24)19(25)20(28-16)27-15-7-3-13(4-8-15)11-26-10-12-1-5-14(22)6-2-12/h1-8,16-25H,9-11H2/t16-,17-,18+,19-,20-/m1/s1
• InChI Key: URINFYYBTXOQCT-OUUBHVDSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₈
• Molecular Weight: 392.40 g/mol
• Exact Mass: 392.14711772 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.29
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• 4-(beta-d-glucopyranosyloxy)benzyl 4-hydroxybenzyl ether
• 77162-64-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8595	85.95%
Caco-2	-	0.8741	87.41%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6816	68.16%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.9265	92.65%
OATP1B3 inhibitior	+	0.9382	93.82%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8188	81.88%
P-glycoprotein inhibitior	-	0.6300	63.00%
P-glycoprotein substrate	-	0.9489	94.89%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8192	81.92%
CYP3A4 inhibition	-	0.9027	90.27%
CYP2C9 inhibition	-	0.8795	87.95%
CYP2C19 inhibition	-	0.8766	87.66%
CYP2D6 inhibition	-	0.9196	91.96%
CYP1A2 inhibition	-	0.9382	93.82%
CYP2C8 inhibition	-	0.5733	57.33%
CYP inhibitory promiscuity	-	0.7848	78.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5997	59.97%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9055	90.55%
Skin irritation	-	0.8492	84.92%
Skin corrosion	-	0.9731	97.31%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4406	44.06%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.8755	87.55%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.6639	66.39%
Acute Oral Toxicity (c)	III	0.5772	57.72%
Estrogen receptor binding	+	0.5547	55.47%
Androgen receptor binding	+	0.6607	66.07%
Thyroid receptor binding	+	0.5668	56.68%
Glucocorticoid receptor binding	-	0.6130	61.30%
Aromatase binding	+	0.5397	53.97%
PPAR gamma	+	0.7338	73.38%
Honey bee toxicity	-	0.6990	69.90%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6450	64.50%
Fish aquatic toxicity	-	0.4509	45.09%

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	97.38%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.85%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.58%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.02%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	88.41%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.35%	95.89%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	87.23%	83.57%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.71%	94.00%
CHEMBL2581	P07339	Cathepsin D	86.34%	98.95%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.14%	85.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.13%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	84.50%	94.73%
CHEMBL242	Q92731	Estrogen receptor beta	84.03%	98.35%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.73%	86.92%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.63%	89.67%

Plants that contains it

• Gastrodia elata

Cross-Links

• PubChem: 11972303
• NPASS: NPC82948
• LOTUS: LTS0035048
• wikiData: Q105277793