3-[6-[[3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]-2,3,4-trihydroxyphenoxy]-4,5-dihydroxybenzoic acid

Details

• Internal ID: df5b9faf-47f7-44cc-abf2-b150a3de77fd
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 3-[6-[[3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]-2,3,4-trihydroxyphenoxy]-4,5-dihydroxybenzoic acid
• SMILES (Canonical): C1=C(C=C(C(=C1O)OC2C(C(C(C(O2)CO)O)O)O)O)COC(=O)C3=CC(=C(C(=C3OC4=CC(=CC(=C4O)O)C(=O)O)O)O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)COC(=O)C3=CC(=C(C(=C3OC4=CC(=CC(=C4O)O)C(=O)O)O)O)O
• InChI: InChI=1S/C27H26O18/c28-6-16-19(35)20(36)22(38)27(44-16)45-24-13(31)1-8(2-14(24)32)7-42-26(41)10-5-12(30)18(34)21(37)23(10)43-15-4-9(25(39)40)3-11(29)17(15)33/h1-5,16,19-20,22,27-38H,6-7H2,(H,39,40)/t16-,19-,20+,22-,27+/m1/s1
• InChI Key: XNGJTVXWNURNOS-OPVSPXBJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₆O₁₈
• Molecular Weight: 638.50 g/mol
• Exact Mass: 638.11191398 g/mol
• Topological Polar Surface Area (TPSA): 314.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.35
• H-Bond Acceptor: 17
• H-Bond Donor: 12
• Rotatable Bonds: 9

Synonyms

• 68735-76-2
• 4-[[[2-(5-Carboxy-2,3-dihydroxyphenoxy)-3,4,5-trihydroxybenzoyl]oxy]methyl]-2,6-dihydroxyphenyl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8486	84.86%
Caco-2	-	0.9057	90.57%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5987	59.87%
OATP2B1 inhibitior	-	0.5626	56.26%
OATP1B1 inhibitior	+	0.8236	82.36%
OATP1B3 inhibitior	+	0.9110	91.10%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.6746	67.46%
P-glycoprotein inhibitior	+	0.6035	60.35%
P-glycoprotein substrate	-	0.8397	83.97%
CYP3A4 substrate	+	0.5859	58.59%
CYP2C9 substrate	-	0.7962	79.62%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.8952	89.52%
CYP2C9 inhibition	-	0.8575	85.75%
CYP2C19 inhibition	-	0.9183	91.83%
CYP2D6 inhibition	-	0.9465	94.65%
CYP1A2 inhibition	-	0.9411	94.11%
CYP2C8 inhibition	+	0.7620	76.20%
CYP inhibitory promiscuity	-	0.8511	85.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7170	71.70%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.8641	86.41%
Skin irritation	-	0.8737	87.37%
Skin corrosion	-	0.9669	96.69%
Ames mutagenesis	-	0.7293	72.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.6752	67.52%
Micronuclear	+	0.5233	52.33%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8775	87.75%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7341	73.41%
Acute Oral Toxicity (c)	III	0.5828	58.28%
Estrogen receptor binding	+	0.7231	72.31%
Androgen receptor binding	+	0.7032	70.32%
Thyroid receptor binding	-	0.5373	53.73%
Glucocorticoid receptor binding	-	0.5778	57.78%
Aromatase binding	-	0.5256	52.56%
PPAR gamma	+	0.6407	64.07%
Honey bee toxicity	-	0.7879	78.79%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7250	72.50%
Fish aquatic toxicity	+	0.8255	82.55%

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	96.88%	91.11%
CHEMBL3194	P02766	Transthyretin	96.60%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.48%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	95.88%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.04%	94.73%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	89.92%	94.42%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.12%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.29%	86.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.31%	97.21%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.23%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.57%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.42%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.35%	95.89%
CHEMBL1811	P34995	Prostanoid EP1 receptor	82.00%	95.71%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.81%	87.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.69%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.36%	85.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.12%	96.95%

Plants that contains it

• Castanea mollissima
• Castanopsis sieboldii

Cross-Links

• PubChem: 102158505
• LOTUS: LTS0033196
• wikiData: Q105331631