[(2R,3S,4S,5R,6R)-6-[[(1R)-7,8-dihydroxy-4-oxo-2,3-dihydro-1H-naphthalen-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Details

• Internal ID: 19163cb9-6515-4d04-afa5-afa94bf06b7c
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives > Gallic acid and derivatives > Galloyl esters
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(1R)-7,8-dihydroxy-4-oxo-2,3-dihydro-1H-naphthalen-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1CC(=O)C2=C(C1OC3C(C(C(C(O3)COC(=O)C4=CC(=C(C(=C4)O)O)O)O)O)O)C(=C(C=C2)O)O
• SMILES (Isomeric): C1CC(=O)C2=C([C@@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C4=CC(=C(C(=C4)O)O)O)O)O)O)C(=C(C=C2)O)O
• InChI: InChI=1S/C23H24O13/c24-10-3-4-14(16-9(10)1-2-11(25)18(16)29)35-23-21(32)20(31)19(30)15(36-23)7-34-22(33)8-5-12(26)17(28)13(27)6-8/h1-2,5-6,14-15,19-21,23,25-32H,3-4,7H2/t14-,15-,19-,20+,21-,23-/m1/s1
• InChI Key: BIEMAGMUKHVOKR-CEGPBPMPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₁₃
• Molecular Weight: 508.40 g/mol
• Exact Mass: 508.12169082 g/mol
• Topological Polar Surface Area (TPSA): 224.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.09
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6991	69.91%
Caco-2	-	0.9096	90.96%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6751	67.51%
OATP2B1 inhibitior	-	0.7072	70.72%
OATP1B1 inhibitior	+	0.7427	74.27%
OATP1B3 inhibitior	+	0.9087	90.87%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5479	54.79%
P-glycoprotein inhibitior	-	0.5318	53.18%
P-glycoprotein substrate	-	0.7491	74.91%
CYP3A4 substrate	+	0.6098	60.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8597	85.97%
CYP3A4 inhibition	-	0.9011	90.11%
CYP2C9 inhibition	-	0.6362	63.62%
CYP2C19 inhibition	-	0.7230	72.30%
CYP2D6 inhibition	-	0.9299	92.99%
CYP1A2 inhibition	-	0.7580	75.80%
CYP2C8 inhibition	+	0.6696	66.96%
CYP inhibitory promiscuity	-	0.8994	89.94%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6968	69.68%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8613	86.13%
Skin irritation	-	0.8196	81.96%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.5101	51.01%
Human Ether-a-go-go-Related Gene inhibition	-	0.4819	48.19%
Micronuclear	-	0.5008	50.08%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8825	88.25%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.9373	93.73%
Acute Oral Toxicity (c)	III	0.5985	59.85%
Estrogen receptor binding	+	0.7539	75.39%
Androgen receptor binding	+	0.6856	68.56%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5392	53.92%
Aromatase binding	-	0.5503	55.03%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8657	86.57%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8759	87.59%

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	99.58%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.10%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.80%	98.95%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	94.22%	83.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.85%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.49%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	90.42%	92.50%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.02%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.53%	99.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.46%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.18%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.68%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.50%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.94%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.29%	92.94%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.87%	95.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.62%	92.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.06%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.68%	95.56%
CHEMBL3194	P02766	Transthyretin	84.60%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.59%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.47%	95.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.65%	94.33%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.50%	90.24%
CHEMBL4208	P20618	Proteasome component C5	80.08%	90.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.00%	93.04%

Plants that contains it

• Juglans sigillata

Cross-Links

• PubChem: 162944937
• LOTUS: LTS0000364
• wikiData: Q104936409