11-o-Galloylbergenin

Details

• Internal ID: 8ca4a264-e7fb-4c49-becd-c8268eebdb0f
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives > Gallic acid and derivatives > Galloyl esters
• IUPAC Name: [(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-9-methoxy-6-oxo-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): COC1=C(C=C2C(=C1O)C3C(C(C(C(O3)COC(=O)C4=CC(=C(C(=C4)O)O)O)O)O)OC2=O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C4=CC(=C(C(=C4)O)O)O)O)O)OC2=O)O
• InChI: InChI=1S/C21H20O13/c1-31-17-10(24)4-7-12(15(17)27)18-19(34-21(7)30)16(28)14(26)11(33-18)5-32-20(29)6-2-8(22)13(25)9(23)3-6/h2-4,11,14,16,18-19,22-28H,5H2,1H3/t11-,14-,16+,18+,19-/m1/s1
• InChI Key: CDRRULDABVKKHU-YQBPHPIXSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₃
• Molecular Weight: 480.40 g/mol
• Exact Mass: 480.09039069 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.22
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• CHEMBL1808739
• 82958-44-9
• DTXSID101315277
• HY-N1023
• BDBM50349520
• AKOS040756354
• CS-0016259

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6437	64.37%
Caco-2	-	0.8500	85.00%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5718	57.18%
OATP2B1 inhibitior	-	0.8447	84.47%
OATP1B1 inhibitior	-	0.6920	69.20%
OATP1B3 inhibitior	+	0.9743	97.43%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5870	58.70%
P-glycoprotein inhibitior	-	0.5825	58.25%
P-glycoprotein substrate	-	0.8098	80.98%
CYP3A4 substrate	+	0.6005	60.05%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.8268	82.68%
CYP3A4 inhibition	-	0.9087	90.87%
CYP2C9 inhibition	-	0.8892	88.92%
CYP2C19 inhibition	-	0.8992	89.92%
CYP2D6 inhibition	-	0.9374	93.74%
CYP1A2 inhibition	-	0.8779	87.79%
CYP2C8 inhibition	+	0.4653	46.53%
CYP inhibitory promiscuity	-	0.8844	88.44%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6669	66.69%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8278	82.78%
Skin irritation	-	0.8266	82.66%
Skin corrosion	-	0.9533	95.33%
Ames mutagenesis	-	0.5008	50.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.7339	73.39%
Micronuclear	+	0.6792	67.92%
Hepatotoxicity	-	0.5842	58.42%
skin sensitisation	-	0.9231	92.31%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9196	91.96%
Acute Oral Toxicity (c)	III	0.6901	69.01%
Estrogen receptor binding	+	0.6227	62.27%
Androgen receptor binding	+	0.6376	63.76%
Thyroid receptor binding	-	0.5410	54.10%
Glucocorticoid receptor binding	+	0.6637	66.37%
Aromatase binding	-	0.5793	57.93%
PPAR gamma	+	0.5463	54.63%
Honey bee toxicity	-	0.8629	86.29%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8319	83.19%

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	98.85%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.87%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.79%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.30%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.78%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	88.02%	94.73%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.84%	83.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.04%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.73%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.49%	98.95%
CHEMBL2535	P11166	Glucose transporter	84.52%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.85%	99.23%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.63%	95.64%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.10%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.06%	96.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.84%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.36%	95.56%
CHEMBL4208	P20618	Proteasome component C5	80.24%	90.00%

Plants that contains it

• Aframomum limbatum
• Andrographis paniculata
• Aristolochia zollingeriana
• Astilbe rubra
• Balanophora involucrata
• Bartramia pomiformis
• Beilschmiedia anacardioides
• Cedrus libani
• Cephalaria kotschyi
• Cerinthe minor
• Craspidospermum verticillatum
• Dioscorea japonica
• Ehretia dicksonii
• Hypericum ascyron
• Ixeris stolonifera
• Jacobaea renardii
• Khaya ivorensis
• Khaya senegalensis
• Larix gmelinii var. gmelinii
• Lotus japonicus
• Lupinus verbasciformis
• Mallotus japonicus
• Melaleuca rhaphiophylla
• Senna siamea
• Sextonia rubra
• Triaenophora rupestris
• Virola multinervia

Cross-Links

• PubChem: 56680102
• NPASS: NPC24627
• ChEMBL: CHEMBL1808739
• LOTUS: LTS0026870
• wikiData: Q104955096