3,4,4'-Tri-O-methylellagic acid

Details

• Internal ID: f98b9842-f384-4bb8-9a9b-0bb4d8af8437
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 7-hydroxy-6,13,14-trimethoxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
• SMILES (Canonical): COC1=C(C2=C3C(=C1)C(=O)OC4=C3C(=CC(=C4OC)OC)C(=O)O2)O
• SMILES (Isomeric): COC1=C(C2=C3C(=C1)C(=O)OC4=C3C(=CC(=C4OC)OC)C(=O)O2)O
• InChI: InChI=1S/C17H12O8/c1-21-8-4-6-10-11-7(16(19)24-14(10)12(8)18)5-9(22-2)13(23-3)15(11)25-17(6)20/h4-5,18H,1-3H3
• InChI Key: NDXSDWFOYZXARW-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂O₈
• Molecular Weight: 344.30 g/mol
• Exact Mass: 344.05321734 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.22
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• DTXSID401301904
• 3,4,4'-Tri-O-methylellagic acid
• 3,3',4'-tri-o-methylellagic acid
• BDBM50428426

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9286	92.86%
Caco-2	+	0.6160	61.60%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6902	69.02%
OATP2B1 inhibitior	-	0.7192	71.92%
OATP1B1 inhibitior	+	0.9268	92.68%
OATP1B3 inhibitior	+	0.9153	91.53%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8255	82.55%
P-glycoprotein inhibitior	-	0.5710	57.10%
P-glycoprotein substrate	-	0.8989	89.89%
CYP3A4 substrate	-	0.5382	53.82%
CYP2C9 substrate	-	0.8431	84.31%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	-	0.8835	88.35%
CYP2C9 inhibition	-	0.9860	98.60%
CYP2C19 inhibition	-	0.9683	96.83%
CYP2D6 inhibition	-	0.9420	94.20%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.5892	58.92%
CYP inhibitory promiscuity	-	0.8735	87.35%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4837	48.37%
Eye corrosion	-	0.9806	98.06%
Eye irritation	+	0.7460	74.60%
Skin irritation	-	0.7433	74.33%
Skin corrosion	-	0.9778	97.78%
Ames mutagenesis	+	0.5136	51.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.7046	70.46%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9343	93.43%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9078	90.78%
Acute Oral Toxicity (c)	II	0.6873	68.73%
Estrogen receptor binding	+	0.7175	71.75%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5425	54.25%
Glucocorticoid receptor binding	+	0.8340	83.40%
Aromatase binding	+	0.7490	74.90%
PPAR gamma	+	0.7030	70.30%
Honey bee toxicity	-	0.8933	89.33%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5449	54.49%
Fish aquatic toxicity	+	0.9282	92.82%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	44100 nM	Ki	PMID: 22892213
CHEMBL3594	Q16790	Carbonic anhydrase IX	17400 nM	Ki	PMID: 22892213
CHEMBL2326	P43166	Carbonic anhydrase VII	8580 nM	Ki	PMID: 22892213
CHEMBL3242	O43570	Carbonic anhydrase XII	7420 nM	Ki	PMID: 22892213
CHEMBL3912	Q8N1Q1	Carbonic anhydrase XIII	5970 nM	Ki	PMID: 22892213

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.89%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.08%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.81%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.36%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.90%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.67%	89.34%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	86.56%	98.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.92%	94.45%
CHEMBL2535	P11166	Glucose transporter	84.39%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.64%	99.17%
CHEMBL2581	P07339	Cathepsin D	81.02%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.99%	99.23%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.75%	94.42%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.51%	92.62%

Plants that contains it

• Aframomum limbatum
• Aglaia elaeagnoidea
• Andrographis paniculata
• Aristolochia littoralis
• Aristolochia zollingeriana
• Astragalus gummifer
• Balanophora involucrata
• Bartramia pomiformis
• Beilschmiedia anacardioides
• Cardiospermum halicacabum
• Cedrus libani
• Centaurea nigrescens
• Cephalaria kotschyi
• Cerinthe minor
• Cirsium japonicum
• Coreopsis fasciculata
• Craspidospermum verticillatum
• Crepis foetida
• Crinum viviparum
• Cuphea carthagenensis
• Cupressus pendula
• Dioscorea japonica
• Dioscoreophyllum cumminsii
• Dorstenia lindeniana
• Ehretia dicksonii
• Erigeron canadensis
• Euphorbia segetalis
• Garcinia celebica
• Hypericum ascyron
• Ixeris stolonifera
• Jacobaea renardii
• Khaya ivorensis
• Khaya senegalensis
• Laguncularia racemosa
• Larix gmelinii var. gmelinii
• Lotus japonicus
• Lupinus verbasciformis
• Mallotus japonicus
• Melaleuca rhaphiophylla
• Ozoroa insignis
• Parastrephia lepidophylla
• Penstemon secundiflorus
• Phedimus kamtschaticus
• Phlogacanthus thyrsiformis
• Phytolacca acinosa
• Piper arboreum
• Pouzolzia occidentalis
• Punica granatum
• Ruta microcarpa
• Selinum carvifolium
• Senna siamea
• Sextonia rubra
• Sidastrum multiflorum
• Syncolostemon parviflorus
• Terminalia ivorensis
• Thuja plicata
• Triaenophora rupestris
• Triglochin maritima
• Urtica triangularis
• Virola multinervia
• Zanthoxylum schreberi

Cross-Links

• PubChem: 11674590
• NPASS: NPC267627
• ChEMBL: CHEMBL2334354
• LOTUS: LTS0145372
• wikiData: Q105177777