[(1R,4S,5R,6S,7R,8S,9S)-5-chloro-4-hydroxy-9-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,10-dioxatricyclo[5.3.1.04,8]undecan-6-yl] 4-hydroxy-3-methoxybenzoate

Details

• Internal ID: cfbfe327-eee1-40af-a381-a1a606a6076b
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [(1R,4S,5R,6S,7R,8S,9S)-5-chloro-4-hydroxy-9-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,10-dioxatricyclo[5.3.1.04,8]undecan-6-yl] 4-hydroxy-3-methoxybenzoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C(=O)OC2C3CC4OCC(C3C(O4)OC5C(C(C(C(O5)CO)O)O)O)(C2Cl)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C(=O)O[C@H]2[C@@H]3C[C@@H]4OC[C@@]([C@H]3[C@@H](O4)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)([C@@H]2Cl)O)O
• InChI: InChI=1S/C23H29ClO13/c1-32-11-4-8(2-3-10(11)26)20(30)36-18-9-5-13-33-7-23(31,19(18)24)14(9)21(35-13)37-22-17(29)16(28)15(27)12(6-25)34-22/h2-4,9,12-19,21-22,25-29,31H,5-7H2,1H3/t9-,12-,13-,14-,15+,16+,17-,18+,19-,21+,22+,23-/m1/s1
• InChI Key: OFCHERKLMXQQJW-WANUOKHUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₉ClO₁₃
• Molecular Weight: 548.90 g/mol
• Exact Mass: 548.1296687 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.57
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7764	77.64%
Caco-2	-	0.8974	89.74%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.4972	49.72%
OATP2B1 inhibitior	-	0.8623	86.23%
OATP1B1 inhibitior	+	0.8315	83.15%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5191	51.91%
P-glycoprotein inhibitior	-	0.6144	61.44%
P-glycoprotein substrate	+	0.5166	51.66%
CYP3A4 substrate	+	0.6987	69.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8388	83.88%
CYP3A4 inhibition	-	0.8852	88.52%
CYP2C9 inhibition	-	0.8498	84.98%
CYP2C19 inhibition	-	0.6694	66.94%
CYP2D6 inhibition	-	0.8493	84.93%
CYP1A2 inhibition	-	0.8110	81.10%
CYP2C8 inhibition	+	0.7956	79.56%
CYP inhibitory promiscuity	-	0.8389	83.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8138	81.38%
Carcinogenicity (trinary)	Non-required	0.5147	51.47%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9310	93.10%
Skin irritation	-	0.7739	77.39%
Skin corrosion	-	0.9377	93.77%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4076	40.76%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.6521	65.21%
skin sensitisation	-	0.8429	84.29%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7317	73.17%
Acute Oral Toxicity (c)	III	0.5225	52.25%
Estrogen receptor binding	+	0.8412	84.12%
Androgen receptor binding	-	0.5223	52.23%
Thyroid receptor binding	+	0.5349	53.49%
Glucocorticoid receptor binding	+	0.6179	61.79%
Aromatase binding	+	0.7050	70.50%
PPAR gamma	+	0.7403	74.03%
Honey bee toxicity	-	0.7096	70.96%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6318	63.18%
Fish aquatic toxicity	+	0.8919	89.19%

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	99.28%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.13%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.24%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.61%	92.94%
CHEMBL4208	P20618	Proteasome component C5	92.35%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.32%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.76%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.42%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.87%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.21%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.93%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.59%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	85.53%	92.50%
CHEMBL2581	P07339	Cathepsin D	85.46%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.45%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.03%	89.62%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.20%	96.61%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.17%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.04%	95.89%
CHEMBL3194	P02766	Transthyretin	83.69%	90.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.78%	91.07%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.44%	90.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.42%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.93%	96.21%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.60%	96.90%
CHEMBL340	P08684	Cytochrome P450 3A4	80.33%	91.19%

Plants that contains it

• Neopicrorhiza scrophulariiflora

Cross-Links

• PubChem: 162962495
• LOTUS: LTS0212596
• wikiData: Q105190827