Ternstroside A

Details

• Internal ID: 06f50e20-b028-4124-b82c-f5df2256deb7
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [(2R,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2-(3,4-dihydroxyphenyl)acetate
• SMILES (Canonical): C1=CC(=C(C=C1CCOC2C(C(C(C(O2)CO)O)O)OC(=O)CC3=CC(=C(C=C3)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1CCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)OC(=O)CC3=CC(=C(C=C3)O)O)O)O
• InChI: InChI=1S/C22H26O11/c23-10-17-19(29)20(30)21(33-18(28)9-12-2-4-14(25)16(27)8-12)22(32-17)31-6-5-11-1-3-13(24)15(26)7-11/h1-4,7-8,17,19-27,29-30H,5-6,9-10H2/t17-,19-,20+,21-,22-/m1/s1
• InChI Key: QAOKYQQABTYYAS-MIUGBVLSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₁₁
• Molecular Weight: 466.40 g/mol
• Exact Mass: 466.14751164 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.34
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• CHEBI:66203
• CHEMBL465424
• DTXSID501130780
• NSC741748
• NSC-741748
• Q27134739
• 2-(3,4-dihydroxyphenyl)ethyl 2-O-(3,4-dihydroxyphenylethanoyl)-beta-D-glucopyranoside
• 2-(3,4-dihydroxyphenyl)ethyl 2-O-[(3,4-dihydroxyphenyl)acetyl]-beta-D-glucopyranoside
• beta-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl, 2-(3,4-dihydroxybenzeneacetate)
• [(2R,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2-(3,4-dihydroxyphenyl)acetate
• 914649-13-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7921	79.21%
Caco-2	-	0.8374	83.74%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7582	75.82%
OATP2B1 inhibitior	+	0.5617	56.17%
OATP1B1 inhibitior	+	0.8558	85.58%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4887	48.87%
P-glycoprotein inhibitior	-	0.6083	60.83%
P-glycoprotein substrate	-	0.8904	89.04%
CYP3A4 substrate	+	0.5473	54.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8569	85.69%
CYP3A4 inhibition	-	0.9017	90.17%
CYP2C9 inhibition	-	0.5372	53.72%
CYP2C19 inhibition	-	0.8384	83.84%
CYP2D6 inhibition	-	0.9226	92.26%
CYP1A2 inhibition	-	0.8955	89.55%
CYP2C8 inhibition	+	0.4529	45.29%
CYP inhibitory promiscuity	-	0.7806	78.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7019	70.19%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8471	84.71%
Skin irritation	-	0.8393	83.93%
Skin corrosion	-	0.9665	96.65%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3954	39.54%
Micronuclear	-	0.6267	62.67%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8545	85.45%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8288	82.88%
Acute Oral Toxicity (c)	III	0.6798	67.98%
Estrogen receptor binding	+	0.8146	81.46%
Androgen receptor binding	+	0.5486	54.86%
Thyroid receptor binding	+	0.5703	57.03%
Glucocorticoid receptor binding	+	0.5875	58.75%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6435	64.35%
Honey bee toxicity	-	0.7828	78.28%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7850	78.50%
Fish aquatic toxicity	+	0.6500	65.00%

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	99.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.25%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.59%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	94.58%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.52%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.53%	98.95%
CHEMBL3194	P02766	Transthyretin	89.26%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	88.60%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.54%	96.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.90%	94.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.06%	99.15%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.39%	96.37%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.40%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	80.41%	91.49%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.22%	94.00%

Plants that contains it

• Ternstroemia gymnanthera

Cross-Links

• PubChem: 16091519
• LOTUS: LTS0198558
• wikiData: Q27134739