3,4,6-trihydroxy-8-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]-1-(3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl)benzo[7]annulen-5-one

Details

• Internal ID: f5fd7980-edc3-4f75-a970-af8d3d7a2070
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: 3,4,6-trihydroxy-8-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]-1-(3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl)benzo[7]annulen-5-one
• SMILES (Canonical): C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC4=C(C(=C(C=C4C5C(CC6=C(C=C(C=C6O5)O)O)O)O)O)C(=O)C(=C3)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC4=C(C(=C(C=C4C5C(CC6=C(C=C(C=C6O5)O)O)O)O)O)C(=O)C(=C3)O)O
• InChI: InChI=1S/C29H24O12/c30-11-3-17(32)15-8-21(36)28(40-23(15)5-11)10-1-13-14(7-20(35)27(39)25(13)26(38)19(34)2-10)29-22(37)9-16-18(33)4-12(31)6-24(16)41-29/h1-7,21-22,28-33,35-37,39H,8-9H2,(H,34,38)/t21-,22?,28-,29?/m1/s1
• InChI Key: IPMYMEWFZKHGAX-PNCIHEHXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₄O₁₂
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.12677620 g/mol
• Topological Polar Surface Area (TPSA): 218.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 12
• H-Bond Donor: 9
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9067	90.67%
Caco-2	-	0.9171	91.71%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4977	49.77%
OATP2B1 inhibitior	-	0.5547	55.47%
OATP1B1 inhibitior	+	0.9061	90.61%
OATP1B3 inhibitior	+	0.9482	94.82%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7883	78.83%
P-glycoprotein inhibitior	+	0.7273	72.73%
P-glycoprotein substrate	-	0.7689	76.89%
CYP3A4 substrate	+	0.5937	59.37%
CYP2C9 substrate	-	0.6050	60.50%
CYP2D6 substrate	-	0.7542	75.42%
CYP3A4 inhibition	+	0.5611	56.11%
CYP2C9 inhibition	-	0.9305	93.05%
CYP2C19 inhibition	-	0.9018	90.18%
CYP2D6 inhibition	-	0.9223	92.23%
CYP1A2 inhibition	-	0.8766	87.66%
CYP2C8 inhibition	+	0.5538	55.38%
CYP inhibitory promiscuity	-	0.9014	90.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6771	67.71%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8026	80.26%
Skin irritation	-	0.5981	59.81%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8955	89.55%
Micronuclear	+	0.8659	86.59%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.7743	77.43%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7125	71.25%
Acute Oral Toxicity (c)	IV	0.4162	41.62%
Estrogen receptor binding	+	0.8517	85.17%
Androgen receptor binding	+	0.7356	73.56%
Thyroid receptor binding	-	0.4909	49.09%
Glucocorticoid receptor binding	+	0.5693	56.93%
Aromatase binding	-	0.5615	56.15%
PPAR gamma	+	0.7431	74.31%
Honey bee toxicity	-	0.7956	79.56%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.7740	77.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4860	P10415	Apoptosis regulator Bcl-2	690 nM	Ki	via Super-PRED
CHEMBL1293224	P10636	Microtubule-associated protein tau	501.2 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	354.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.82%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.62%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.54%	94.45%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	92.89%	95.55%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.66%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.43%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.90%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.51%	97.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	87.19%	96.12%
CHEMBL1951	P21397	Monoamine oxidase A	85.65%	91.49%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.48%	95.64%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.68%	96.37%
CHEMBL3401	O75469	Pregnane X receptor	82.58%	94.73%
CHEMBL2535	P11166	Glucose transporter	82.07%	98.75%
CHEMBL217	P14416	Dopamine D2 receptor	81.85%	95.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.83%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.79%	99.15%
CHEMBL3194	P02766	Transthyretin	81.74%	90.71%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.54%	83.10%

Plants that contains it

• Camellia sinensis

Cross-Links

• PubChem: 136453467
• LOTUS: LTS0192787
• wikiData: Q104253497