Theaflavin 3

Details

• Internal ID: e3ee7657-b4f9-404a-8fca-2433fc5f77a5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Catechin gallates
• IUPAC Name: [(2R,3R)-2-[1-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-3,4,5-trihydroxy-6-oxobenzo[7]annulen-8-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)C(=C4C(=C3)C(=CC(=C4O)O)C5C(CC6=C(C=C(C=C6O5)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C(=CC(=C4O)O)[C@@H]5[C@@H](CC6=C(C=C(C=C6O5)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)O)O)O
• InChI: InChI=1S/C43H32O20/c44-17-7-23(46)21-12-33(62-42(58)15-3-25(48)36(54)26(49)4-15)40(60-31(21)9-17)14-1-19-20(11-30(53)39(57)35(19)38(56)29(52)2-14)41-34(13-22-24(47)8-18(45)10-32(22)61-41)63-43(59)16-5-27(50)37(55)28(51)6-16/h1-11,33-34,40-41,44-51,53-55,57H,12-13H2,(H,52,56)/t33-,34-,40-,41-/m1/s1
• InChI Key: ZEASWHWETFMWCV-ISBUVJFSSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₃₂O₂₀
• Molecular Weight: 868.70 g/mol
• Exact Mass: 868.14869341 g/mol
• Topological Polar Surface Area (TPSA): 351.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 4.18
• H-Bond Acceptor: 20
• H-Bond Donor: 13
• Rotatable Bonds: 6

Synonyms

• THEAFLAVIN3,3-DI-O-GALLATE
• AKOS040758746
• (2R,2'R,3R,3'R)-2,2'-(3,4,5-Trihydroxy-6-oxo-6H-benzo[7]annulene-1,8-diyl)bis(5,7-dihydroxychroman-3,2-diyl) bis(3,4,5-trihydroxybenzoate)
• (3,4,5-trihydroxy-6-oxo-6h-benzo[7]annulene-1,8-diyl)bis[(2r,3r)-5,7-dihydroxy-3,4-dihydro-2h-chromene-2,3-diyl] bis(3,4,5-trihydroxybenzoate)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7133	71.33%
Caco-2	-	0.8893	88.93%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5768	57.68%
OATP2B1 inhibitior	-	0.7065	70.65%
OATP1B1 inhibitior	-	0.6387	63.87%
OATP1B3 inhibitior	+	0.9658	96.58%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7146	71.46%
P-glycoprotein inhibitior	+	0.7345	73.45%
P-glycoprotein substrate	-	0.6026	60.26%
CYP3A4 substrate	+	0.6690	66.90%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.7884	78.84%
CYP3A4 inhibition	-	0.7173	71.73%
CYP2C9 inhibition	-	0.8544	85.44%
CYP2C19 inhibition	-	0.7533	75.33%
CYP2D6 inhibition	-	0.9573	95.73%
CYP1A2 inhibition	-	0.9260	92.60%
CYP2C8 inhibition	+	0.7970	79.70%
CYP inhibitory promiscuity	-	0.9381	93.81%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6773	67.73%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8785	87.85%
Skin irritation	-	0.6978	69.78%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7491	74.91%
Micronuclear	+	0.8559	85.59%
Hepatotoxicity	+	0.7754	77.54%
skin sensitisation	-	0.8713	87.13%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7747	77.47%
Acute Oral Toxicity (c)	II	0.3538	35.38%
Estrogen receptor binding	+	0.7572	75.72%
Androgen receptor binding	+	0.8152	81.52%
Thyroid receptor binding	+	0.5271	52.71%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5153	51.53%
PPAR gamma	+	0.6629	66.29%
Honey bee toxicity	-	0.7659	76.59%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6350	63.50%
Fish aquatic toxicity	+	0.9354	93.54%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	2754.23 nM	IC50	PMID: 23571415
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	4466.84 nM	IC50	PMID: 23571415

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.73%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.33%	91.49%
CHEMBL4302	P08183	P-glycoprotein 1	96.36%	92.98%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.59%	99.23%
CHEMBL3194	P02766	Transthyretin	93.35%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.11%	89.00%
CHEMBL2581	P07339	Cathepsin D	91.99%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.42%	97.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.21%	83.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.44%	86.33%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	90.36%	96.37%
CHEMBL2535	P11166	Glucose transporter	88.84%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.78%	95.56%
CHEMBL1929	P47989	Xanthine dehydrogenase	87.44%	96.12%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.25%	95.64%
CHEMBL1993	P26358	DNA (cytosine-5)-methyltransferase 1	87.01%	95.44%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.51%	99.17%
CHEMBL2056	P21728	Dopamine D1 receptor	85.34%	91.00%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	85.14%	95.55%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.20%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.73%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	81.18%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.70%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.67%	95.78%

Plants that contains it

• Zingiber officinale

Cross-Links

• PubChem: 467320
• NPASS: NPC112380
• ChEMBL: CHEMBL434864