[(3S,4R,5S)-5-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

Details

• Internal ID: 80ee832f-a0ad-4146-80f9-0e87a6a64363
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [(3S,4R,5S)-5-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C(=O)OCC2(COC(C2O)OC3C(C(C(OC3OCCC4=CC=C(C=C4)O)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C(=O)OC[C@]2(CO[C@H]([C@@H]2O)O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3OCCC4=CC=C(C=C4)O)CO)O)O)O)O
• InChI: InChI=1S/C27H34O14/c1-36-18-10-15(4-7-17(18)30)24(34)38-12-27(35)13-39-26(23(27)33)41-22-21(32)20(31)19(11-28)40-25(22)37-9-8-14-2-5-16(29)6-3-14/h2-7,10,19-23,25-26,28-33,35H,8-9,11-13H2,1H3/t19-,20-,21+,22-,23+,25-,26+,27-/m1/s1
• InChI Key: JCVAJYVLSZBGRV-DVKXAIPJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₄
• Molecular Weight: 582.50 g/mol
• Exact Mass: 582.19485575 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.20
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 11

Synonyms

• CHEMBL4207523

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6401	64.01%
Caco-2	-	0.8887	88.87%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7672	76.72%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.8656	86.56%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5507	55.07%
P-glycoprotein inhibitior	-	0.4475	44.75%
P-glycoprotein substrate	+	0.5524	55.24%
CYP3A4 substrate	+	0.6905	69.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8377	83.77%
CYP3A4 inhibition	-	0.8874	88.74%
CYP2C9 inhibition	-	0.7853	78.53%
CYP2C19 inhibition	-	0.8349	83.49%
CYP2D6 inhibition	-	0.9020	90.20%
CYP1A2 inhibition	-	0.8701	87.01%
CYP2C8 inhibition	+	0.8452	84.52%
CYP inhibitory promiscuity	-	0.8277	82.77%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5671	56.71%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9175	91.75%
Skin irritation	-	0.8128	81.28%
Skin corrosion	-	0.9419	94.19%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3993	39.93%
Micronuclear	-	0.6167	61.67%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8647	86.47%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8543	85.43%
Acute Oral Toxicity (c)	III	0.7339	73.39%
Estrogen receptor binding	+	0.8199	81.99%
Androgen receptor binding	+	0.6424	64.24%
Thyroid receptor binding	-	0.5356	53.56%
Glucocorticoid receptor binding	+	0.5794	57.94%
Aromatase binding	+	0.6201	62.01%
PPAR gamma	+	0.6660	66.60%
Honey bee toxicity	-	0.7454	74.54%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	-	0.5630	56.30%

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	99.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.09%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.72%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.52%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.25%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.23%	86.33%
CHEMBL4208	P20618	Proteasome component C5	90.51%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.99%	95.89%
CHEMBL3194	P02766	Transthyretin	88.87%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.74%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.68%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	88.61%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.02%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	86.22%	91.19%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	85.29%	85.00%
CHEMBL2581	P07339	Cathepsin D	85.19%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.23%	90.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.00%	94.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.98%	94.62%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	82.88%	97.03%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.10%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.97%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.70%	96.90%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.88%	86.92%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.76%	96.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.26%	96.00%

Plants that contains it

• Catalpa ovata
• Phlomis grandiflora
• Rauvolfia serpentina

Cross-Links

• PubChem: 100978506
• NPASS: NPC226759
• LOTUS: LTS0062469
• wikiData: Q105125147