2-O,3-O-[4,4',5,5',6,6'-Hexahydroxy-1,1'-biphenyl-2,2'-diylbis(carbonyl)]-beta-D-glucopyranose

Details

• Internal ID: 260f7c32-6ea4-4183-abf4-c2f71d6f74dd
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: (10R,11R,13R,14R,15S)-3,4,5,11,14,20,21,22-octahydroxy-13-(hydroxymethyl)-9,12,16-trioxatetracyclo[16.4.0.02,7.010,15]docosa-1(22),2,4,6,18,20-hexaene-8,17-dione
• SMILES (Canonical): C1=C2C(=C(C(=C1O)O)O)C3=C(C(=C(C=C3C(=O)OC4C(C(C(OC4O)CO)O)OC2=O)O)O)O
• SMILES (Isomeric): C1=C2C(=C(C(=C1O)O)O)C3=C(C(=C(C=C3C(=O)O[C@@H]4[C@H]([C@@H]([C@H](O[C@H]4O)CO)O)OC2=O)O)O)O
• InChI: InChI=1S/C20H18O14/c21-3-8-13(26)16-17(20(31)32-8)34-19(30)5-2-7(23)12(25)15(28)10(5)9-4(18(29)33-16)1-6(22)11(24)14(9)27/h1-2,8,13,16-17,20-28,31H,3H2/t8-,13-,16+,17-,20-/m1/s1
• InChI Key: GEAGRKQCZVLNAU-FYHMHJJZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₁₄
• Molecular Weight: 482.30 g/mol
• Exact Mass: 482.06965524 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.28
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 1

Synonyms

• 2-O,3-O-[4,4',5,5',6,6'-Hexahydroxy-1,1'-biphenyl-2,2'-diylbis(carbonyl)]-beta-D-glucopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6723	67.23%
Caco-2	-	0.9045	90.45%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4685	46.85%
OATP2B1 inhibitior	+	0.5842	58.42%
OATP1B1 inhibitior	-	0.3843	38.43%
OATP1B3 inhibitior	+	0.9718	97.18%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8764	87.64%
P-glycoprotein inhibitior	-	0.7266	72.66%
P-glycoprotein substrate	-	0.9436	94.36%
CYP3A4 substrate	-	0.5232	52.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8424	84.24%
CYP3A4 inhibition	-	0.9286	92.86%
CYP2C9 inhibition	-	0.9306	93.06%
CYP2C19 inhibition	-	0.9383	93.83%
CYP2D6 inhibition	-	0.9633	96.33%
CYP1A2 inhibition	-	0.9491	94.91%
CYP2C8 inhibition	-	0.8680	86.80%
CYP inhibitory promiscuity	-	0.9600	96.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7351	73.51%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.6723	67.23%
Skin irritation	-	0.8013	80.13%
Skin corrosion	-	0.9599	95.99%
Ames mutagenesis	-	0.5823	58.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.5607	56.07%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.5915	59.15%
skin sensitisation	-	0.8749	87.49%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.5987	59.87%
Acute Oral Toxicity (c)	IV	0.3971	39.71%
Estrogen receptor binding	+	0.6034	60.34%
Androgen receptor binding	+	0.6193	61.93%
Thyroid receptor binding	-	0.6112	61.12%
Glucocorticoid receptor binding	-	0.5146	51.46%
Aromatase binding	-	0.6021	60.21%
PPAR gamma	+	0.5988	59.88%
Honey bee toxicity	-	0.8958	89.58%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8147	81.47%

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	99.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.76%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.96%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.61%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.87%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.47%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.06%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.54%	86.92%

Plants that contains it

• Aframomum limbatum
• Aglaia elaeagnoidea
• Alnus japonica
• Andrographis paniculata
• Aristolochia littoralis
• Aristolochia zollingeriana
• Astragalus gummifer
• Balanophora involucrata
• Bartramia pomiformis
• Beilschmiedia anacardioides
• Camellia japonica
• Cardiospermum halicacabum
• Castanopsis fissa
• Cedrus libani
• Centaurea nigrescens
• Cephalaria kotschyi
• Cerinthe minor
• Cirsium japonicum
• Coreopsis fasciculata
• Craspidospermum verticillatum
• Crepis foetida
• Crinum viviparum
• Cuphea carthagenensis
• Dioscorea japonica
• Dioscoreophyllum cumminsii
• Dorstenia lindeniana
• Ehretia dicksonii
• Elaeagnus umbellata
• Erigeron canadensis
• Euphorbia segetalis
• Euphorbia thymifolia
• Garcinia celebica
• Hypericum ascyron
• Ixeris stolonifera
• Jacobaea renardii
• Juglans regia
• Khaya ivorensis
• Khaya senegalensis
• Lagerstroemia speciosa
• Larix gmelinii var. gmelinii
• Lonicera caerulea
• Lotus japonicus
• Lupinus verbasciformis
• Mallotus japonicus
• Melaleuca rhaphiophylla
• Osbeckia chinensis
• Ozoroa insignis
• Paeonia lactiflora
• Parastrephia lepidophylla
• Penstemon secundiflorus
• Phedimus kamtschaticus
• Phlogacanthus thyrsiformis
• Phyllanthus emblica
• Phytolacca acinosa
• Piper arboreum
• Platycarya strobilacea
• Pleroma semidecandrum
• Pouzolzia occidentalis
• Punica granatum
• Rhoiptelea chiliantha
• Rubus sanctus
• Ruta microcarpa
• Selinum carvifolium
• Senna siamea
• Sextonia rubra
• Sidastrum multiflorum
• Stachyurus praecox
• Syncolostemon parviflorus
• Terminalia catappa
• Terminalia myriocarpa
• Thuja plicata
• Triaenophora rupestris
• Triglochin maritima
• Urtica triangularis
• Virola multinervia
• Zanthoxylum schreberi

Cross-Links

• PubChem: 11754973
• NPASS: NPC135222
• LOTUS: LTS0033259
• wikiData: Q105007054