(2R,3R)-2-[(3aS,3bS,8aS)-3-[(2R,3R)-3,4-Dihydro-3,5,7-trihydroxy-2H-1-benzopyran-2-yl]-3a,6,8,8a-tetrahydro-5,7,8a-trihydroxy-1,6,8-trioxocyclopent[a]inden-3b(1H)-yl]-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

Details

• Internal ID: 44994f23-a9a3-48c3-bfe6-494eb0364e4b
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives > Gallic acid and derivatives > Galloyl esters
• IUPAC Name: [(2R,3R)-2-[(3aS,8aS,8bS)-3a,5,7-trihydroxy-3,4,6-trioxo-1-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]-8bH-cyclopenta[a]inden-8a-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=O)C4(C3C5(C=C(C(=O)C(=C5C4=O)O)O)C6C(CC7=C(C=C(C=C7O6)O)O)OC(=O)C8=CC(=C(C(=C8)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=O)[C@]4([C@@H]3[C@]5(C=C(C(=O)C(=C5C4=O)O)O)[C@@H]6[C@@H](CC7=C(C=C(C=C7O6)O)O)OC(=O)C8=CC(=C(C(=C8)O)O)O)O)O
• InChI: InChI=1S/C37H28O18/c38-12-3-17(40)14-7-21(44)31(53-23(14)5-12)16-9-26(46)37(52)32(16)36(10-22(45)29(48)30(49)27(36)33(37)50)34-25(8-15-18(41)4-13(39)6-24(15)54-34)55-35(51)11-1-19(42)28(47)20(43)2-11/h1-6,9-10,21,25,31-32,34,38-45,47,49,52H,7-8H2/t21-,25-,31-,32+,34+,36-,37-/m1/s1
• InChI Key: WCQMIZTZMRUYPY-ZDJLAWDKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₂₈O₁₈
• Molecular Weight: 760.60 g/mol
• Exact Mass: 760.12756404 g/mol
• Topological Polar Surface Area (TPSA): 319.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.78
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 4

Synonyms

• (2R,3R)-2-[(3aS,3bS,8aS)-3-[(2R,3R)-3,4-Dihydro-3,5,7-trihydroxy-2H-1-benzopyran-2-yl]-3a,6,8,8a-tetrahydro-5,7,8a-trihydroxy-1,6,8-trioxocyclopent[a]inden-3b(1H)-yl]-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
• 201998-49-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9396	93.96%
Caco-2	-	0.8930	89.30%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6585	65.85%
OATP2B1 inhibitior	-	0.7056	70.56%
OATP1B1 inhibitior	-	0.3163	31.63%
OATP1B3 inhibitior	+	0.9235	92.35%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7227	72.27%
P-glycoprotein inhibitior	+	0.7388	73.88%
P-glycoprotein substrate	+	0.5821	58.21%
CYP3A4 substrate	+	0.7078	70.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8599	85.99%
CYP3A4 inhibition	-	0.7352	73.52%
CYP2C9 inhibition	-	0.5615	56.15%
CYP2C19 inhibition	-	0.6092	60.92%
CYP2D6 inhibition	-	0.8778	87.78%
CYP1A2 inhibition	-	0.9086	90.86%
CYP2C8 inhibition	+	0.7197	71.97%
CYP inhibitory promiscuity	-	0.8327	83.27%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4714	47.14%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.8871	88.71%
Skin irritation	-	0.7050	70.50%
Skin corrosion	-	0.9265	92.65%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7365	73.65%
Micronuclear	+	0.8059	80.59%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.7750	77.50%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.2856	28.56%
Estrogen receptor binding	+	0.7817	78.17%
Androgen receptor binding	+	0.7657	76.57%
Thyroid receptor binding	+	0.5553	55.53%
Glucocorticoid receptor binding	+	0.5993	59.93%
Aromatase binding	-	0.4902	49.02%
PPAR gamma	+	0.7342	73.42%
Honey bee toxicity	-	0.6868	68.68%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5650	56.50%
Fish aquatic toxicity	+	0.9750	97.50%

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	99.15%	91.11%
CHEMBL4302	P08183	P-glycoprotein 1	96.33%	92.98%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	96.24%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.09%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.79%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.54%	98.95%
CHEMBL3194	P02766	Transthyretin	91.79%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.65%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.48%	93.40%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	89.33%	97.53%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.35%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	87.73%	91.19%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.12%	83.00%
CHEMBL2535	P11166	Glucose transporter	86.62%	98.75%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.50%	96.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.75%	92.94%
CHEMBL1951	P21397	Monoamine oxidase A	85.70%	91.49%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.40%	85.11%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.65%	94.42%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.27%	91.07%
CHEMBL1929	P47989	Xanthine dehydrogenase	82.85%	96.12%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.06%	85.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.83%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.79%	95.89%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.52%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.96%	94.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.83%	96.37%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.17%	93.04%

Plants that contains it

• Camellia sinensis

Cross-Links

• PubChem: 132472926
• LOTUS: LTS0149420
• wikiData: Q105302018