1-(5-Carboxy-2,3-dihydroxyphenoxy)-3-(6-carboxy-2,3,4-trihydroxyphenyl)-8-[[6,7,8,11,12,13,22-heptahydroxy-21-(hydroxymethyl)-3,16-dioxo-2,17,20-trioxatetracyclo[16.3.1.04,9.010,15]docosa-4,6,8,10,12,14-hexaen-19-yl]oxycarbonyl]-4,6-dihydroxydibenzo-p-dioxin-2-carboxylic acid

Details

• Internal ID: 856c7c8e-86c0-412d-836f-2cc68a49cd33
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 1-(5-carboxy-2,3-dihydroxyphenoxy)-3-(6-carboxy-2,3,4-trihydroxyphenyl)-8-[[6,7,8,11,12,13,22-heptahydroxy-21-(hydroxymethyl)-3,16-dioxo-2,17,20-trioxatetracyclo[16.3.1.04,9.010,15]docosa-4,6,8,10,12,14-hexaen-19-yl]oxycarbonyl]-4,6-dihydroxydibenzo-p-dioxin-2-carboxylic acid
• SMILES (Canonical): C1=C(C=C2C(=C1O)OC3=C(C(=C(C(=C3O2)OC4=CC(=CC(=C4O)O)C(=O)O)C(=O)O)C5=C(C(=C(C=C5C(=O)O)O)O)O)O)C(=O)OC6C7C(C(C(O6)CO)OC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O7)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=C(C=C2C(=C1O)OC3=C(C(=C(C(=C3O2)OC4=CC(=CC(=C4O)O)C(=O)O)C(=O)O)C5=C(C(=C(C=C5C(=O)O)O)O)O)O)C(=O)OC6C7C(C(C(O6)CO)OC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O7)O)O)O)O)O)O)O
• InChI: InChI=1S/C48H32O31/c49-8-21-37-35(63)40(78-47(72)13-7-17(53)30(58)33(61)24(13)23-12(46(71)77-37)6-16(52)29(57)32(23)60)48(75-21)79-45(70)10-2-18(54)36-20(4-10)74-41-38(73-19-3-9(42(64)65)1-14(50)27(19)55)26(44(68)69)25(34(62)39(41)76-36)22-11(43(66)67)5-15(51)28(56)31(22)59/h1-7,21,35,37,40,48-63H,8H2,(H,64,65)(H,66,67)(H,68,69)
• InChI Key: MZUSVKVKDSKMEX-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₃₂O₃₁
• Molecular Weight: 1104.70 g/mol
• Exact Mass: 1104.09275422 g/mol
• Topological Polar Surface Area (TPSA): 531.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.98
• H-Bond Acceptor: 28
• H-Bond Donor: 18
• Rotatable Bonds: 9

Synonyms

• alpha-D-Glucopyranose, cyclic 3,6-(3-(5-carboxy-2,3-dihydroxyphenoxy)-4,4',5,5'.6.6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylate) cyclic 2,4-(4,4',5,5',6,6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylate) 1-(3,4,5-trihydroxybenzoate), stereoisomer

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6297	62.97%
Caco-2	-	0.8675	86.75%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5955	59.55%
OATP2B1 inhibitior	-	0.5699	56.99%
OATP1B1 inhibitior	+	0.7399	73.99%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7057	70.57%
P-glycoprotein inhibitior	+	0.7340	73.40%
P-glycoprotein substrate	+	0.5061	50.61%
CYP3A4 substrate	+	0.6714	67.14%
CYP2C9 substrate	-	0.7969	79.69%
CYP2D6 substrate	-	0.8606	86.06%
CYP3A4 inhibition	-	0.8426	84.26%
CYP2C9 inhibition	-	0.8428	84.28%
CYP2C19 inhibition	-	0.9296	92.96%
CYP2D6 inhibition	-	0.9485	94.85%
CYP1A2 inhibition	-	0.9298	92.98%
CYP2C8 inhibition	+	0.8197	81.97%
CYP inhibitory promiscuity	-	0.7831	78.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7236	72.36%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.8921	89.21%
Skin irritation	-	0.8250	82.50%
Skin corrosion	-	0.9624	96.24%
Ames mutagenesis	-	0.6423	64.23%
Human Ether-a-go-go-Related Gene inhibition	+	0.7813	78.13%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9107	91.07%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6988	69.88%
Acute Oral Toxicity (c)	III	0.3880	38.80%
Estrogen receptor binding	+	0.7168	71.68%
Androgen receptor binding	+	0.6828	68.28%
Thyroid receptor binding	+	0.5339	53.39%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5847	58.47%
PPAR gamma	+	0.7324	73.24%
Honey bee toxicity	-	0.7091	70.91%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7450	74.50%
Fish aquatic toxicity	+	0.8593	85.93%

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	98.64%	91.11%
CHEMBL3194	P02766	Transthyretin	96.28%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.72%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.61%	99.23%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.61%	89.34%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	92.02%	87.67%
CHEMBL2581	P07339	Cathepsin D	91.86%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.68%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.17%	86.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	91.12%	94.42%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	90.34%	83.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.13%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.89%	95.50%
CHEMBL1811	P34995	Prostanoid EP1 receptor	89.58%	95.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.39%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	88.14%	94.73%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.13%	97.21%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.91%	95.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.36%	89.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.28%	95.78%
CHEMBL2535	P11166	Glucose transporter	84.21%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.43%	96.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.63%	93.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.36%	83.57%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.00%	96.37%

Plants that contains it

• Rosa henryi
• Rubus idaeus

Cross-Links

• PubChem: 16131110
• LOTUS: LTS0075542
• wikiData: Q105176077