[(3R,4R,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(3,4,5-trimethoxyphenoxy)oxan-3-yl]oxy-4-hydroxy-3-(hydroxymethyl)oxolan-3-yl] 4-hydroxy-3-methoxybenzoate

Details

• Internal ID: 89a16a04-d10e-4e58-b509-09098755bf94
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [(3R,4R,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(3,4,5-trimethoxyphenoxy)oxan-3-yl]oxy-4-hydroxy-3-(hydroxymethyl)oxolan-3-yl] 4-hydroxy-3-methoxybenzoate
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)OC2C(C(C(C(O2)CO)O)O)OC3C(C(CO3)(CO)OC(=O)C4=CC(=C(C=C4)O)OC)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O[C@H]3[C@@H]([C@](CO3)(CO)OC(=O)C4=CC(=C(C=C4)O)OC)O
• InChI: InChI=1S/C28H36O16/c1-36-16-7-13(5-6-15(16)31)25(35)44-28(11-30)12-40-27(24(28)34)43-23-21(33)20(32)19(10-29)42-26(23)41-14-8-17(37-2)22(39-4)18(9-14)38-3/h5-9,19-21,23-24,26-27,29-34H,10-12H2,1-4H3/t19-,20-,21+,23-,24+,26-,27+,28-/m1/s1
• InChI Key: HLVCFVZCXITDLJ-NSUMHAEISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₁₆
• Molecular Weight: 628.60 g/mol
• Exact Mass: 628.20033506 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -1.07
• H-Bond Acceptor: 16
• H-Bond Donor: 6
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7216	72.16%
Caco-2	-	0.8640	86.40%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7265	72.65%
OATP2B1 inhibitior	-	0.7215	72.15%
OATP1B1 inhibitior	+	0.9020	90.20%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7034	70.34%
P-glycoprotein inhibitior	+	0.6574	65.74%
P-glycoprotein substrate	-	0.6386	63.86%
CYP3A4 substrate	+	0.6645	66.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8436	84.36%
CYP3A4 inhibition	-	0.8510	85.10%
CYP2C9 inhibition	-	0.8373	83.73%
CYP2C19 inhibition	-	0.8121	81.21%
CYP2D6 inhibition	-	0.9322	93.22%
CYP1A2 inhibition	-	0.8621	86.21%
CYP2C8 inhibition	+	0.7287	72.87%
CYP inhibitory promiscuity	-	0.6047	60.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5883	58.83%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9209	92.09%
Skin irritation	-	0.8529	85.29%
Skin corrosion	-	0.9561	95.61%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4028	40.28%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8568	85.68%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8018	80.18%
Acute Oral Toxicity (c)	III	0.7096	70.96%
Estrogen receptor binding	+	0.8126	81.26%
Androgen receptor binding	+	0.5637	56.37%
Thyroid receptor binding	+	0.5870	58.70%
Glucocorticoid receptor binding	+	0.7488	74.88%
Aromatase binding	+	0.6823	68.23%
PPAR gamma	+	0.7271	72.71%
Honey bee toxicity	-	0.7752	77.52%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.7077	70.77%

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	99.33%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.69%	96.09%
CHEMBL4208	P20618	Proteasome component C5	94.05%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.03%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.61%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.24%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.28%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.09%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.51%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.14%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.62%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.49%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.83%	92.94%
CHEMBL3194	P02766	Transthyretin	82.65%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.92%	95.83%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.85%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.63%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	80.20%	91.19%

Plants that contains it

• Markhamia stipulata
• Santisukia kerrii

Cross-Links

• PubChem: 101182720
• LOTUS: LTS0236176
• wikiData: Q105030315