[(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

Details

• Internal ID: 289092e0-6aa2-4231-b6f0-a07eb5a7b017
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl 4-hydroxy-3-methoxybenzoate
• SMILES (Canonical): CC12CC3(C4CC1(C4(C(O2)O3)COC(=O)C5=CC(=C(C=C5)O)OC)OC6C(C(C(C(O6)CO)O)O)O)O
• SMILES (Isomeric): C[C@]12C[C@@]3([C@@H]4C[C@]1([C@@]4([C@H](O2)O3)COC(=O)C5=CC(=C(C=C5)O)OC)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
• InChI: InChI=1S/C24H30O13/c1-21-8-23(31)14-6-24(21,35-19-17(29)16(28)15(27)13(7-25)34-19)22(14,20(36-21)37-23)9-33-18(30)10-3-4-11(26)12(5-10)32-2/h3-5,13-17,19-20,25-29,31H,6-9H2,1-2H3/t13-,14-,15-,16+,17-,19+,20-,21+,22+,23-,24+/m1/s1
• InChI Key: VMBNWSNNKXQGBU-KTBSYUCQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₁₃
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.16864101 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.64
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7826	78.26%
Caco-2	-	0.8472	84.72%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5602	56.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9146	91.46%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5419	54.19%
P-glycoprotein inhibitior	-	0.5318	53.18%
P-glycoprotein substrate	-	0.6011	60.11%
CYP3A4 substrate	+	0.6887	68.87%
CYP2C9 substrate	-	0.7992	79.92%
CYP2D6 substrate	-	0.8424	84.24%
CYP3A4 inhibition	-	0.7847	78.47%
CYP2C9 inhibition	-	0.9034	90.34%
CYP2C19 inhibition	-	0.8163	81.63%
CYP2D6 inhibition	-	0.9197	91.97%
CYP1A2 inhibition	-	0.8244	82.44%
CYP2C8 inhibition	+	0.7338	73.38%
CYP inhibitory promiscuity	-	0.9379	93.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6077	60.77%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9256	92.56%
Skin irritation	-	0.7637	76.37%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.7270	72.70%
skin sensitisation	-	0.8664	86.64%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8986	89.86%
Acute Oral Toxicity (c)	III	0.3816	38.16%
Estrogen receptor binding	+	0.8155	81.55%
Androgen receptor binding	+	0.7329	73.29%
Thyroid receptor binding	+	0.5903	59.03%
Glucocorticoid receptor binding	+	0.6506	65.06%
Aromatase binding	+	0.7409	74.09%
PPAR gamma	+	0.6990	69.90%
Honey bee toxicity	-	0.7884	78.84%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5466	54.66%
Fish aquatic toxicity	+	0.9475	94.75%

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	99.27%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.44%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.94%	86.33%
CHEMBL220	P22303	Acetylcholinesterase	92.48%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.73%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.43%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.33%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.51%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.30%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.39%	95.83%
CHEMBL4208	P20618	Proteasome component C5	86.69%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.17%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.78%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.37%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.31%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.34%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	83.27%	91.19%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.06%	96.90%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.59%	96.61%

Plants that contains it

• Paeonia suffruticosa

Cross-Links

• PubChem: 21631104
• NPASS: NPC119900