Eschweilenol C

Details

• Internal ID: 0d17960d-d11c-4b72-a6e8-395b2caeb23b
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 6,7,14-trihydroxy-13-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-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): CC1C(C(C(C(O1)OC2=C(C3=C4C(=C2)C(=O)OC5=C4C(=CC(=C5O)O)C(=O)O3)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C3=C4C(=C2)C(=O)OC5=C4C(=CC(=C5O)O)C(=O)O3)O)O)O)O
• InChI: InChI=1S/C20H16O12/c1-4-11(22)14(25)15(26)20(29-4)30-8-3-6-10-9-5(18(27)32-17(10)13(8)24)2-7(21)12(23)16(9)31-19(6)28/h2-4,11,14-15,20-26H,1H3/t4-,11-,14+,15+,20-/m0/s1
• InChI Key: NLOYJHDXNPMFKW-RGYXEVLJSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₆O₁₂
• Molecular Weight: 448.30 g/mol
• Exact Mass: 448.06417594 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.19
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

• 4-(alpha-Rhamnopyranosyl)ellagic acid
• 6,7,14-trihydroxy-13-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
• Ellagic acid deoxyhexoside
• CHEMBL516559
• CHEBI:167701
• BDBM50478560
• AKOS040735356
• 211371-02-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6842	68.42%
Caco-2	-	0.8774	87.74%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6405	64.05%
OATP2B1 inhibitior	+	0.5839	58.39%
OATP1B1 inhibitior	+	0.9230	92.30%
OATP1B3 inhibitior	+	0.9762	97.62%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7013	70.13%
P-glycoprotein inhibitior	-	0.7562	75.62%
P-glycoprotein substrate	-	0.7818	78.18%
CYP3A4 substrate	+	0.5350	53.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8627	86.27%
CYP3A4 inhibition	-	0.8636	86.36%
CYP2C9 inhibition	-	0.9246	92.46%
CYP2C19 inhibition	-	0.9045	90.45%
CYP2D6 inhibition	-	0.9634	96.34%
CYP1A2 inhibition	-	0.6077	60.77%
CYP2C8 inhibition	-	0.6466	64.66%
CYP inhibitory promiscuity	-	0.8580	85.80%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6362	63.62%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.8785	87.85%
Skin irritation	-	0.6354	63.54%
Skin corrosion	-	0.9116	91.16%
Ames mutagenesis	+	0.5462	54.62%
Human Ether-a-go-go-Related Gene inhibition	-	0.5540	55.40%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8753	87.53%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9008	90.08%
Acute Oral Toxicity (c)	III	0.5992	59.92%
Estrogen receptor binding	+	0.7067	70.67%
Androgen receptor binding	+	0.5387	53.87%
Thyroid receptor binding	+	0.5181	51.81%
Glucocorticoid receptor binding	+	0.8130	81.30%
Aromatase binding	-	0.4835	48.35%
PPAR gamma	+	0.6475	64.75%
Honey bee toxicity	-	0.8420	84.20%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5049	50.49%
Fish aquatic toxicity	+	0.9502	95.02%

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	99.67%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.70%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.22%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.47%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.39%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.48%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.84%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.74%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.17%	92.94%
CHEMBL3401	O75469	Pregnane X receptor	86.05%	94.73%
CHEMBL3194	P02766	Transthyretin	85.43%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.58%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.55%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.39%	99.23%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.21%	89.34%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.32%	83.57%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.06%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.52%	99.17%

Plants that contains it

• Aglaia elaeagnoidea
• Aristolochia littoralis
• Astragalus gummifer
• Cardiospermum halicacabum
• Centaurea nigrescens
• Cirsium japonicum
• Combretum griffithii var. yunnanense
• Coreopsis fasciculata
• Crepis foetida
• Crinum viviparum
• Cuphea carthagenensis
• Dioscoreophyllum cumminsii
• Dorstenia lindeniana
• Erigeron canadensis
• Eschweilera coriacea
• Euphorbia segetalis
• Garcinia celebica
• Myrciaria dubia
• Ozoroa insignis
• Parastrephia lepidophylla
• Penstemon secundiflorus
• Phedimus kamtschaticus
• Phlogacanthus thyrsiformis
• Phytolacca acinosa
• Piper arboreum
• Pouzolzia occidentalis
• Punica granatum
• Ruta microcarpa
• Selinum carvifolium
• Sidastrum multiflorum
• Siphoneugena densiflora
• Syncolostemon parviflorus
• Thuja plicata
• Triglochin maritima
• Urtica triangularis
• Zanthoxylum schreberi

Cross-Links

• PubChem: 10026656
• NPASS: NPC219600
• LOTUS: LTS0124075
• wikiData: Q104399184