[(2R,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-2-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxan-2-yl]methoxy]oxolan-3-yl] 3,4,5-trihydroxybenzoate

Details

• Internal ID: aca61759-1939-498f-87d5-1cccfafd5e78
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives > Gallic acid and derivatives > Galloyl esters
• IUPAC Name: [(2R,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-2-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxan-2-yl]methoxy]oxolan-3-yl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): CC1=CCC(CC1)C(C)(C)OC2C(C(C(C(O2)COC3C(C(C(O3)CO)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)O)O)O
• SMILES (Isomeric): CC1=CC[C@@H](CC1)C(C)(C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H](O3)CO)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)O)O)O
• InChI: InChI=1S/C28H40O14/c1-12-4-6-14(7-5-12)28(2,3)42-26-23(36)22(35)20(33)18(40-26)11-38-27-24(21(34)17(10-29)39-27)41-25(37)13-8-15(30)19(32)16(31)9-13/h4,8-9,14,17-18,20-24,26-27,29-36H,5-7,10-11H2,1-3H3/t14-,17-,18+,20+,21-,22-,23+,24+,26-,27+/m0/s1
• InChI Key: ZPXRVNRKZYBYHR-CRIMJPFASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₁₄
• Molecular Weight: 600.60 g/mol
• Exact Mass: 600.24180595 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• (4R)-8-[6-O-(2-O-Galloyl-alpha-L-arabinofuranosyl)-beta-D-glucopyranosyloxy]-p-mentha-1-ene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7718	77.18%
Caco-2	-	0.8768	87.68%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8821	88.21%
OATP2B1 inhibitior	-	0.8626	86.26%
OATP1B1 inhibitior	+	0.7673	76.73%
OATP1B3 inhibitior	+	0.8300	83.00%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5800	58.00%
P-glycoprotein inhibitior	-	0.4923	49.23%
P-glycoprotein substrate	-	0.6491	64.91%
CYP3A4 substrate	+	0.6677	66.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8595	85.95%
CYP3A4 inhibition	-	0.7962	79.62%
CYP2C9 inhibition	-	0.7090	70.90%
CYP2C19 inhibition	-	0.7515	75.15%
CYP2D6 inhibition	-	0.8868	88.68%
CYP1A2 inhibition	-	0.6915	69.15%
CYP2C8 inhibition	+	0.7251	72.51%
CYP inhibitory promiscuity	-	0.7246	72.46%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6239	62.39%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9286	92.86%
Skin irritation	-	0.7321	73.21%
Skin corrosion	-	0.9499	94.99%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6616	66.16%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8949	89.49%
Acute Oral Toxicity (c)	III	0.4993	49.93%
Estrogen receptor binding	+	0.7232	72.32%
Androgen receptor binding	+	0.6067	60.67%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5792	57.92%
Aromatase binding	+	0.6678	66.78%
PPAR gamma	+	0.6813	68.13%
Honey bee toxicity	-	0.8399	83.99%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9913	99.13%

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	99.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.67%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.97%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.96%	96.09%
CHEMBL5255	O00206	Toll-like receptor 4	92.28%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.76%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.52%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.35%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.02%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.49%	89.00%
CHEMBL4581	P52732	Kinesin-like protein 1	88.04%	93.18%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.13%	89.34%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.81%	95.89%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.37%	95.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.14%	100.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.74%	83.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.01%	80.78%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.61%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.49%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.72%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.62%	94.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.54%	97.21%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.03%	95.64%
CHEMBL1873	P00750	Tissue-type plasminogen activator	81.87%	93.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.52%	96.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.04%	97.36%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.99%	94.33%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.40%	98.75%
CHEMBL3194	P02766	Transthyretin	80.12%	90.71%

Plants that contains it

• Artemisia afra
• Epipactis palustris
• Pimenta dioica
• Rumex obtusifolius

Cross-Links

• PubChem: 24879406
• NPASS: NPC4747
• ChEMBL: CHEMBL500762
• LOTUS: LTS0218973
• wikiData: Q105381296