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

Details

• Internal ID: 03037d2e-7570-481e-a473-2c31cc337150
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: 3,4,5-trihydroxy-8-[(2R,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]-1-[(2S,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]benzo[7]annulen-6-one
• 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)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)O)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-/m0/s1
• InChI Key: IPMYMEWFZKHGAX-RGTUZWOVSA-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: 0.60
• 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	-	0.9281	92.81%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.4977	49.77%
OATP2B1 inhibitior	+	0.5846	58.46%
OATP1B1 inhibitior	+	0.8567	85.67%
OATP1B3 inhibitior	+	0.9482	94.82%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8419	84.19%
P-glycoprotein inhibitior	+	0.7213	72.13%
P-glycoprotein substrate	-	0.7260	72.60%
CYP3A4 substrate	+	0.5976	59.76%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.6965	69.65%
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	+	0.5728	57.28%
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	-	0.7806	78.06%
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	+	0.8155	81.55%
Micronuclear	+	0.8659	86.59%
Hepatotoxicity	+	0.6305	63.05%
skin sensitisation	-	0.7743	77.43%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7098	70.98%
Acute Oral Toxicity (c)	IV	0.4162	41.62%
Estrogen receptor binding	+	0.8716	87.16%
Androgen receptor binding	+	0.7554	75.54%
Thyroid receptor binding	+	0.5494	54.94%
Glucocorticoid receptor binding	+	0.6181	61.81%
Aromatase binding	-	0.5529	55.29%
PPAR gamma	+	0.7153	71.53%
Honey bee toxicity	-	0.7977	79.77%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.7740	77.40%

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	99.79%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.85%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.67%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL1929	P47989	Xanthine dehydrogenase	92.28%	96.12%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	92.17%	95.55%
CHEMBL1951	P21397	Monoamine oxidase A	91.94%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.47%	99.23%
CHEMBL2581	P07339	Cathepsin D	90.95%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.43%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.87%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.68%	99.15%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.06%	96.37%
CHEMBL217	P14416	Dopamine D2 receptor	82.79%	95.62%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.82%	95.64%
CHEMBL2535	P11166	Glucose transporter	81.66%	98.75%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.34%	91.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.13%	100.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.07%	83.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.57%	86.33%
CHEMBL3194	P02766	Transthyretin	80.14%	90.71%

Plants that contains it

• Camellia sinensis

Cross-Links

• PubChem: 101324904
• NPASS: NPC124371