(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(1S,2S)-1-(3,4-dihydroxyphenyl)-2-hydroxy-3-(2,4,6-trihydroxyphenyl)propyl]-3,4-dihydro-2H-chromene-3,5,7-triol

Details

• Internal ID: c8ca3bbf-fbd4-4910-a38c-07cef7e84d68
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(1S,2S)-1-(3,4-dihydroxyphenyl)-2-hydroxy-3-(2,4,6-trihydroxyphenyl)propyl]-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC(=C2C(C3=CC(=C(C=C3)O)O)C(CC4=C(C=C(C=C4O)O)O)O)O)O)C5=CC(=C(C=C5)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@H](C3=CC(=C(C=C3)O)O)[C@H](CC4=C(C=C(C=C4O)O)O)O)O)O)C5=CC(=C(C=C5)O)O)O
• InChI: InChI=1S/C30H28O12/c31-14-7-19(34)15(20(35)8-14)9-24(39)27(12-1-3-17(32)22(37)5-12)28-25(40)11-21(36)16-10-26(41)29(42-30(16)28)13-2-4-18(33)23(38)6-13/h1-8,11,24,26-27,29,31-41H,9-10H2/t24-,26-,27+,29+/m0/s1
• InChI Key: AAOPKIFUFWCDQZ-VIUUMSQESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₈O₁₂
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.15807632 g/mol
• Topological Polar Surface Area (TPSA): 232.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 12
• H-Bond Donor: 11
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8516	85.16%
Caco-2	-	0.8940	89.40%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.4431	44.31%
OATP2B1 inhibitior	+	0.5721	57.21%
OATP1B1 inhibitior	+	0.8854	88.54%
OATP1B3 inhibitior	+	0.9296	92.96%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9069	90.69%
P-glycoprotein inhibitior	+	0.6824	68.24%
P-glycoprotein substrate	-	0.5793	57.93%
CYP3A4 substrate	+	0.5828	58.28%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	+	0.5264	52.64%
CYP3A4 inhibition	-	0.8156	81.56%
CYP2C9 inhibition	-	0.9113	91.13%
CYP2C19 inhibition	-	0.8950	89.50%
CYP2D6 inhibition	-	0.9204	92.04%
CYP1A2 inhibition	-	0.9235	92.35%
CYP2C8 inhibition	+	0.5896	58.96%
CYP inhibitory promiscuity	-	0.7318	73.18%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6049	60.49%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.8346	83.46%
Skin irritation	-	0.6310	63.10%
Skin corrosion	-	0.9364	93.64%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9524	95.24%
Micronuclear	+	0.7918	79.18%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.7421	74.21%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.9234	92.34%
Acute Oral Toxicity (c)	IV	0.5636	56.36%
Estrogen receptor binding	+	0.7816	78.16%
Androgen receptor binding	+	0.7595	75.95%
Thyroid receptor binding	+	0.6471	64.71%
Glucocorticoid receptor binding	+	0.5719	57.19%
Aromatase binding	-	0.5241	52.41%
PPAR gamma	+	0.7564	75.64%
Honey bee toxicity	-	0.5977	59.77%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7367	73.67%

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	99.64%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.61%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.55%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.92%	97.09%
CHEMBL233	P35372	Mu opioid receptor	91.57%	97.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.56%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.20%	99.15%
CHEMBL2535	P11166	Glucose transporter	88.23%	98.75%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.12%	96.12%
CHEMBL2581	P07339	Cathepsin D	87.77%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.37%	94.45%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	85.61%	96.37%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.39%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.36%	93.40%
CHEMBL3401	O75469	Pregnane X receptor	83.95%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.63%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.20%	95.56%
CHEMBL4208	P20618	Proteasome component C5	82.68%	90.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.40%	83.10%

Plants that contains it

• Uncaria gambir

Cross-Links

• PubChem: 101406540
• NPASS: NPC236898