1-O,3-O-Digalloyl-4-O,6-O-[(4,4',5,5',6,6'-hexahydroxy-2,2'-biphenylylene)biscarbonyl]-beta-D-glucopyranose

Details

• Internal ID: d588056d-2a6a-4971-8331-9f4d97d8c169
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [(10R,11R,12R,13S,15R)-3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-13-(3,4,5-trihydroxybenzoyl)oxy-9,14,17-trioxatetracyclo[17.4.0.02,7.010,15]tricosa-1(23),2,4,6,19,21-hexaen-11-yl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1C2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5C6=C(C(=C(C=C6C(=O)O1)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5C6=C(C(=C(C=C6C(=O)O1)O)O)O)O)O)O
• InChI: InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(48)55-29-27(47)34(56-31(49)9-3-14(37)22(42)15(38)4-9)53-18-7-52-32(50)10-5-16(39)23(43)25(45)19(10)20-11(33(51)54-28(18)29)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-47H,7H2/t18-,27-,28-,29-,34+/m1/s1
• InChI Key: NLDMNSXOCDLTTB-LQZDAVIGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₂₆O₂₂
• Molecular Weight: 786.60 g/mol
• Exact Mass: 786.09157245 g/mol
• Topological Polar Surface Area (TPSA): 377.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.69
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 4

Synonyms

• 1-O,3-O-Digalloyl-4-O,6-O-[(4,4',5,5',6,6'-hexahydroxy-2,2'-biphenylylene)biscarbonyl]-beta-D-glucopyranose
• 1-O,3-O-Digalloyl-4-O,6-O-[[(aS)-4,4',5,5',6,6'-hexahydroxybiphenyl-2,2'-diyl]biscarbonyl]-beta-D-glucopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6260	62.60%
Caco-2	-	0.8907	89.07%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6215	62.15%
OATP2B1 inhibitior	-	0.5609	56.09%
OATP1B1 inhibitior	+	0.7131	71.31%
OATP1B3 inhibitior	+	0.9124	91.24%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7396	73.96%
P-glycoprotein inhibitior	+	0.7297	72.97%
P-glycoprotein substrate	-	0.6890	68.90%
CYP3A4 substrate	+	0.6212	62.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8364	83.64%
CYP3A4 inhibition	-	0.8556	85.56%
CYP2C9 inhibition	-	0.8626	86.26%
CYP2C19 inhibition	-	0.8499	84.99%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	-	0.8350	83.50%
CYP2C8 inhibition	+	0.5286	52.86%
CYP inhibitory promiscuity	-	0.9047	90.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6996	69.96%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8552	85.52%
Skin irritation	-	0.7725	77.25%
Skin corrosion	-	0.9531	95.31%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7811	78.11%
Micronuclear	+	0.7933	79.33%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8273	82.73%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8619	86.19%
Acute Oral Toxicity (c)	III	0.5277	52.77%
Estrogen receptor binding	+	0.7515	75.15%
Androgen receptor binding	+	0.7123	71.23%
Thyroid receptor binding	-	0.5222	52.22%
Glucocorticoid receptor binding	-	0.4728	47.28%
Aromatase binding	-	0.6130	61.30%
PPAR gamma	+	0.6626	66.26%
Honey bee toxicity	-	0.8274	82.74%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	98.96%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.04%	91.49%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	92.84%	83.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.22%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.80%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.33%	95.64%
CHEMBL2581	P07339	Cathepsin D	88.06%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.92%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.44%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.63%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.99%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.25%	99.17%
CHEMBL3194	P02766	Transthyretin	84.78%	90.71%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.78%	96.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.42%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.58%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.05%	99.15%
CHEMBL4208	P20618	Proteasome component C5	81.00%	90.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.88%	95.17%
CHEMBL3401	O75469	Pregnane X receptor	80.68%	94.73%

Plants that contains it

• Aconitum sajanense
• Artemisia jacutica
• Balanophora japonica
• Balanophora laxiflora
• Bersama abyssinica
• Damnacanthus major
• Dryopteris aitoniana
• Hedyosmum arborescens
• Juglans regia
• Piper attenuatum
• Psorospermum adamauense
• Rubus sanctus
• Senna santanderensis
• Stauntonia hexaphylla
• Strychnos trinervis
• Syzygium aromaticum
• Vachellia tortilis subsp. raddiana

Cross-Links

• PubChem: 10056061
• NPASS: NPC302170
• LOTUS: LTS0109156
• wikiData: Q105181289