[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl] 3,4,5-trihydroxy-2-(6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl)benzoate

Details

• Internal ID: 44a22736-4f7b-445f-8bda-de497ed58bad
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl] 3,4,5-trihydroxy-2-(6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl)benzoate
• SMILES (Canonical): C1=C2C3=C(C(=C1O)O)OC(=O)C4=C3C(=C(C(=C4C5=C(C(=C(C=C5C(=O)OC6C(OC(C(C6O)O)O)CO)O)O)O)O)O)OC2=O
• SMILES (Isomeric): C1=C2C3=C(C(=C1O)O)OC(=O)C4=C3C(=C(C(=C4C5=C(C(=C(C=C5C(=O)O[C@@H]6[C@H](O[C@H]([C@@H]([C@H]6O)O)O)CO)O)O)O)O)O)OC2=O
• InChI: InChI=1S/C27H20O18/c28-3-8-21(19(36)20(37)27(41)42-8)43-24(38)4-1-6(29)14(31)16(33)9(4)11-13-12-10-5(25(39)44-23(12)18(35)17(11)34)2-7(30)15(32)22(10)45-26(13)40/h1-2,8,19-21,27-37,41H,3H2/t8-,19-,20-,21-,27-/m1/s1
• InChI Key: KLGPORNWEXMEEM-PFLNWGCMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₀O₁₈
• Molecular Weight: 632.40 g/mol
• Exact Mass: 632.06496378 g/mol
• Topological Polar Surface Area (TPSA): 311.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -0.95
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6297	62.97%
Caco-2	-	0.9299	92.99%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5955	59.55%
OATP2B1 inhibitior	-	0.5548	55.48%
OATP1B1 inhibitior	+	0.7971	79.71%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6112	61.12%
P-glycoprotein inhibitior	-	0.5565	55.65%
P-glycoprotein substrate	-	0.6852	68.52%
CYP3A4 substrate	+	0.6092	60.92%
CYP2C9 substrate	-	0.8094	80.94%
CYP2D6 substrate	-	0.8543	85.43%
CYP3A4 inhibition	-	0.8426	84.26%
CYP2C9 inhibition	-	0.8428	84.28%
CYP2C19 inhibition	-	0.9296	92.96%
CYP2D6 inhibition	-	0.9485	94.85%
CYP1A2 inhibition	-	0.9298	92.98%
CYP2C8 inhibition	+	0.6012	60.12%
CYP inhibitory promiscuity	-	0.7831	78.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7236	72.36%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.8625	86.25%
Skin irritation	-	0.8250	82.50%
Skin corrosion	-	0.9624	96.24%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6428	64.28%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9107	91.07%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.9318	93.18%
Acute Oral Toxicity (c)	III	0.3880	38.80%
Estrogen receptor binding	+	0.7745	77.45%
Androgen receptor binding	+	0.6848	68.48%
Thyroid receptor binding	-	0.5114	51.14%
Glucocorticoid receptor binding	+	0.5576	55.76%
Aromatase binding	-	0.5067	50.67%
PPAR gamma	+	0.6725	67.25%
Honey bee toxicity	-	0.8049	80.49%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8593	85.93%

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	99.69%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.68%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.77%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.79%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.66%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.14%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.39%	86.92%
CHEMBL3194	P02766	Transthyretin	88.48%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	88.46%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.97%	96.21%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.84%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.47%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.08%	99.15%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.52%	94.42%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.40%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.36%	97.36%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.80%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.68%	95.89%

Plants that contains it

• Terminalia chebula

Cross-Links

• PubChem: 101587737
• LOTUS: LTS0139979
• wikiData: Q104397099