(2S,3S)-8-[(R)-[(2S)-4,6-dihydroxy-2,3-dihydro-1-benzofuran-2-yl]-(3,4-dihydroxyphenyl)methyl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

Details

• Internal ID: 2953243f-dbd9-49db-85eb-d1fd6f26b9a0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: (2S,3S)-8-[(R)-[(2S)-4,6-dihydroxy-2,3-dihydro-1-benzofuran-2-yl]-(3,4-dihydroxyphenyl)methyl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC(=C2C(C3CC4=C(C=C(C=C4O3)O)O)C5=CC(=C(C=C5)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@@H](OC2=C1C(=CC(=C2[C@H]([C@@H]3CC4=C(C=C(C=C4O3)O)O)C5=CC(=C(C=C5)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• InChI: InChI=1S/C30H26O11/c31-14-7-19(34)15-10-26(40-25(15)8-14)27(12-1-3-17(32)21(36)5-12)28-23(38)11-20(35)16-9-24(39)29(41-30(16)28)13-2-4-18(33)22(37)6-13/h1-8,11,24,26-27,29,31-39H,9-10H2/t24-,26-,27-,29-/m0/s1
• InChI Key: YQTLJOBSWBOCRZ-CXXWFMJBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₆O₁₁
• Molecular Weight: 562.50 g/mol
• Exact Mass: 562.14751164 g/mol
• Topological Polar Surface Area (TPSA): 201.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 11
• H-Bond Donor: 9
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9217	92.17%
Caco-2	-	0.9001	90.01%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5905	59.05%
OATP2B1 inhibitior	-	0.5663	56.63%
OATP1B1 inhibitior	+	0.8597	85.97%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9324	93.24%
P-glycoprotein inhibitior	+	0.7200	72.00%
P-glycoprotein substrate	-	0.6487	64.87%
CYP3A4 substrate	+	0.5751	57.51%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	+	0.5264	52.64%
CYP3A4 inhibition	-	0.7748	77.48%
CYP2C9 inhibition	-	0.8402	84.02%
CYP2C19 inhibition	-	0.8339	83.39%
CYP2D6 inhibition	-	0.8578	85.78%
CYP1A2 inhibition	-	0.8328	83.28%
CYP2C8 inhibition	+	0.5531	55.31%
CYP inhibitory promiscuity	-	0.7472	74.72%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4774	47.74%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8365	83.65%
Skin irritation	-	0.6388	63.88%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9297	92.97%
Micronuclear	+	0.8159	81.59%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.7743	77.43%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6990	69.90%
Acute Oral Toxicity (c)	IV	0.4356	43.56%
Estrogen receptor binding	+	0.7755	77.55%
Androgen receptor binding	+	0.7898	78.98%
Thyroid receptor binding	+	0.6264	62.64%
Glucocorticoid receptor binding	+	0.5997	59.97%
Aromatase binding	-	0.5207	52.07%
PPAR gamma	+	0.7454	74.54%
Honey bee toxicity	-	0.6534	65.34%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.7493	74.93%

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	98.39%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.30%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.22%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.44%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.35%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.98%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.72%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.28%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	89.56%	96.12%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	88.68%	97.23%
CHEMBL2535	P11166	Glucose transporter	88.66%	98.75%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	88.61%	96.37%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	87.54%	85.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.18%	89.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	84.60%	97.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.29%	95.89%
CHEMBL236	P41143	Delta opioid receptor	84.21%	99.35%
CHEMBL3401	O75469	Pregnane X receptor	84.14%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.03%	95.56%
CHEMBL3194	P02766	Transthyretin	82.55%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.47%	90.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	82.06%	83.10%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.64%	93.99%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.67%	100.00%

Plants that contains it

• Uncaria gambir

Cross-Links

• PubChem: 101438322
• NPASS: NPC273791