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

Details

• Internal ID: 10720e26-0410-428d-8399-e7d9c221162c
• 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,6S)-3,4,5-trihydroxy-6-[2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): CC1=CCC(CC1)C(C)(C)OC2C(C(C(C(O2)COC(=O)C3=CC(=C(C(=C3)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)COC(=O)C3=CC(=C(C(=C3)O)O)O)O)O)O
• InChI: InChI=1S/C23H32O10/c1-11-4-6-13(7-5-11)23(2,3)33-22-20(29)19(28)18(27)16(32-22)10-31-21(30)12-8-14(24)17(26)15(25)9-12/h4,8-9,13,16,18-20,22,24-29H,5-7,10H2,1-3H3/t13-,16+,18+,19-,20+,22-/m0/s1
• InChI Key: SGZVUALRBMIRIV-AZAWAHRISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₂O₁₀
• Molecular Weight: 468.50 g/mol
• Exact Mass: 468.19954721 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.31
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• 1-[(1R)-4-Methyl-3-cyclohexenyl]-1-methylethyl 6-O-galloyl-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8458	84.58%
Caco-2	-	0.8407	84.07%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8991	89.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7971	79.71%
OATP1B3 inhibitior	-	0.2218	22.18%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	-	0.7876	78.76%
P-glycoprotein inhibitior	-	0.5761	57.61%
P-glycoprotein substrate	-	0.7943	79.43%
CYP3A4 substrate	+	0.6393	63.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8578	85.78%
CYP3A4 inhibition	-	0.8497	84.97%
CYP2C9 inhibition	-	0.5088	50.88%
CYP2C19 inhibition	+	0.5078	50.78%
CYP2D6 inhibition	-	0.8740	87.40%
CYP1A2 inhibition	+	0.6725	67.25%
CYP2C8 inhibition	+	0.6931	69.31%
CYP inhibitory promiscuity	-	0.7340	73.40%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7141	71.41%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9379	93.79%
Skin irritation	-	0.7513	75.13%
Skin corrosion	-	0.9592	95.92%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4789	47.89%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8030	80.30%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.9433	94.33%
Acute Oral Toxicity (c)	III	0.5808	58.08%
Estrogen receptor binding	+	0.7017	70.17%
Androgen receptor binding	+	0.6463	64.63%
Thyroid receptor binding	+	0.6350	63.50%
Glucocorticoid receptor binding	+	0.6446	64.46%
Aromatase binding	+	0.5187	51.87%
PPAR gamma	+	0.6324	63.24%
Honey bee toxicity	-	0.8961	89.61%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9961	99.61%

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	99.12%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	95.00%	94.73%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.00%	95.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.17%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.21%	96.09%
CHEMBL5255	O00206	Toll-like receptor 4	91.28%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.99%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.79%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.67%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.10%	97.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.88%	83.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.18%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.62%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.21%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.08%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.85%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.40%	90.71%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.88%	97.21%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.59%	95.64%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.40%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.36%	96.61%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.36%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.28%	95.56%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.06%	90.24%

Plants that contains it

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

Cross-Links

• PubChem: 10695593
• NPASS: NPC156624
• LOTUS: LTS0092713
• wikiData: Q105252745