5-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S)-3,4-dihydroxy-4-[(4-hydroxy-3,5-dimethoxybenzoyl)oxymethyl]oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxybenzoic acid

Details

• Internal ID: 0339e270-cf41-4c0f-82b0-de4a88e4d393
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 5-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S)-3,4-dihydroxy-4-[(4-hydroxy-3,5-dimethoxybenzoyl)oxymethyl]oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxybenzoic acid
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C(=O)OCC2(COC(C2O)OC3C(C(C(OC3OC4=CC(=C(C=C4)O)C(=O)O)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C(=O)OC[C@]2(CO[C@H]([C@@H]2O)O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3OC4=CC(=C(C=C4)O)C(=O)O)CO)O)O)O
• InChI: InChI=1S/C27H32O17/c1-38-15-5-11(6-16(39-2)18(15)30)24(36)40-9-27(37)10-41-26(22(27)33)44-21-20(32)19(31)17(8-28)43-25(21)42-12-3-4-14(29)13(7-12)23(34)35/h3-7,17,19-22,25-26,28-33,37H,8-10H2,1-2H3,(H,34,35)/t17-,19-,20+,21-,22+,25-,26+,27-/m1/s1
• InChI Key: VFEYSSLJKRGMAH-RCQOEAOESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₇
• Molecular Weight: 628.50 g/mol
• Exact Mass: 628.16394955 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.68
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7272	72.72%
Caco-2	-	0.8836	88.36%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6299	62.99%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.8689	86.89%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5168	51.68%
P-glycoprotein inhibitior	+	0.6411	64.11%
P-glycoprotein substrate	-	0.5669	56.69%
CYP3A4 substrate	+	0.6502	65.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8755	87.55%
CYP3A4 inhibition	-	0.8356	83.56%
CYP2C9 inhibition	-	0.8761	87.61%
CYP2C19 inhibition	-	0.8862	88.62%
CYP2D6 inhibition	-	0.9319	93.19%
CYP1A2 inhibition	-	0.8900	89.00%
CYP2C8 inhibition	+	0.7116	71.16%
CYP inhibitory promiscuity	-	0.8565	85.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6228	62.28%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9144	91.44%
Skin irritation	-	0.8461	84.61%
Skin corrosion	-	0.9449	94.49%
Ames mutagenesis	-	0.6623	66.23%
Human Ether-a-go-go-Related Gene inhibition	+	0.6773	67.73%
Micronuclear	+	0.5233	52.33%
Hepatotoxicity	-	0.6432	64.32%
skin sensitisation	-	0.8460	84.60%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.9088	90.88%
Acute Oral Toxicity (c)	III	0.7343	73.43%
Estrogen receptor binding	+	0.7880	78.80%
Androgen receptor binding	+	0.5332	53.32%
Thyroid receptor binding	-	0.5237	52.37%
Glucocorticoid receptor binding	+	0.6498	64.98%
Aromatase binding	+	0.6473	64.73%
PPAR gamma	+	0.6889	68.89%
Honey bee toxicity	-	0.7748	77.48%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7333	73.33%
Fish aquatic toxicity	+	0.6954	69.54%

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	99.43%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.00%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.80%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.77%	94.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	93.04%	94.42%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.74%	99.17%
CHEMBL4208	P20618	Proteasome component C5	91.73%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.05%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.34%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.24%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.97%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.60%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.05%	97.09%
CHEMBL2243	O00519	Anandamide amidohydrolase	87.53%	97.53%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.06%	92.94%
CHEMBL3194	P02766	Transthyretin	87.00%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.66%	92.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.45%	94.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.34%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.27%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.38%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	83.26%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.12%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	80.45%	95.93%

Plants that contains it

• Albizia lebbeck

Cross-Links

• PubChem: 101938056
• LOTUS: LTS0148581
• wikiData: Q105285184