[(1R,19S,21R,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.04,9.010,15]tricosa-4,6,8,10,12,14-hexaen-21-yl] 3,4,5-trihydroxybenzoate

Details

• Internal ID: fecb4fc0-38b4-41d2-a50b-710aaabbb1f2
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [(1R,19S,21R,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.04,9.010,15]tricosa-4,6,8,10,12,14-hexaen-21-yl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1C2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)O)OC(=O)C4=CC(=C(C(=C4C5=C(C(=C(C=C5C(=O)O1)O)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]2[C@H]([C@H]([C@H]([C@H](O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)O)OC(=O)C4=CC(=C(C(=C4C5=C(C(=C(C=C5C(=O)O1)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H22O18/c28-9-1-6(2-10(29)16(9)32)24(39)45-27-22(38)23-19(35)13(43-27)5-42-25(40)7-3-11(30)17(33)20(36)14(7)15-8(26(41)44-23)4-12(31)18(34)21(15)37/h1-4,13,19,22-23,27-38H,5H2/t13-,19+,22+,23+,27+/m0/s1
• InChI Key: TUSDEZXZIZRFGC-AYCRMCRVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₂O₁₈
• Molecular Weight: 634.50 g/mol
• Exact Mass: 634.08061385 g/mol
• Topological Polar Surface Area (TPSA): 311.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.30
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6364	63.64%
Caco-2	-	0.9021	90.21%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5868	58.68%
OATP2B1 inhibitior	-	0.5560	55.60%
OATP1B1 inhibitior	+	0.7421	74.21%
OATP1B3 inhibitior	+	0.9166	91.66%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6075	60.75%
P-glycoprotein inhibitior	+	0.6416	64.16%
P-glycoprotein substrate	-	0.7530	75.30%
CYP3A4 substrate	+	0.6123	61.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8374	83.74%
CYP3A4 inhibition	-	0.9116	91.16%
CYP2C9 inhibition	-	0.9083	90.83%
CYP2C19 inhibition	-	0.8377	83.77%
CYP2D6 inhibition	-	0.9575	95.75%
CYP1A2 inhibition	-	0.8596	85.96%
CYP2C8 inhibition	+	0.5841	58.41%
CYP inhibitory promiscuity	-	0.9485	94.85%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7032	70.32%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8200	82.00%
Skin irritation	-	0.7789	77.89%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7560	75.60%
Micronuclear	+	0.7833	78.33%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8461	84.61%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8778	87.78%
Acute Oral Toxicity (c)	III	0.4887	48.87%
Estrogen receptor binding	+	0.7861	78.61%
Androgen receptor binding	+	0.6582	65.82%
Thyroid receptor binding	-	0.5478	54.78%
Glucocorticoid receptor binding	+	0.5426	54.26%
Aromatase binding	-	0.5687	56.87%
PPAR gamma	+	0.6836	68.36%
Honey bee toxicity	-	0.7992	79.92%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8983	89.83%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2392	P06746	DNA polymerase beta	158.5 nM	Potency	via Super-PRED
CHEMBL2362978	P43351	DNA repair protein RAD52 homolog	500 nM	IC50	via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	50.1 nM	Potency	via Super-PRED
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	100 nM	Potency	via Super-PRED
CHEMBL2095202	P63316	Troponin, cardiac muscle	676.76 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.51%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	91.61%	91.49%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	90.78%	83.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.25%	94.00%
CHEMBL2581	P07339	Cathepsin D	88.40%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.42%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.09%	95.56%
CHEMBL3194	P02766	Transthyretin	86.49%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.74%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.49%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.25%	99.23%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.78%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	82.45%	94.73%
CHEMBL4208	P20618	Proteasome component C5	81.55%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.05%	99.15%
CHEMBL2535	P11166	Glucose transporter	80.93%	98.75%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.32%	95.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.25%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.25%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.20%	92.50%

Plants that contains it

• Phyllanthus emblica
• Terminalia anogeissiana

Cross-Links

• PubChem: 162888061
• LOTUS: LTS0015830
• wikiData: Q105327795