(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-2,3-dihydrochromen-4-one

Details

• Internal ID: a269438b-8893-4015-b1c2-3881e9a052c4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: (2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C1=O)C(=CC(=C2)O)OC3C(C(C(OC3O)CO)O)O)C4=CC(=C(C=C4)O)O
• SMILES (Isomeric): C1[C@H](OC2=C(C1=O)C(=CC(=C2)O)O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3O)CO)O)O)C4=CC(=C(C=C4)O)O
• InChI: InChI=1S/C21H22O11/c22-7-16-18(27)19(28)20(21(29)32-16)31-15-5-9(23)4-14-17(15)12(26)6-13(30-14)8-1-2-10(24)11(25)3-8/h1-5,13,16,18-25,27-29H,6-7H2/t13-,16+,18+,19-,20+,21+/m0/s1
• InChI Key: HLWFWCCEDRONPH-ITSUVCJSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₁
• Molecular Weight: 450.40 g/mol
• Exact Mass: 450.11621151 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.31
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9303	93.03%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	-	0.5646	56.46%
OATP1B1 inhibitior	+	0.9227	92.27%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.7297	72.97%
P-glycoprotein substrate	-	0.8324	83.24%
CYP3A4 substrate	+	0.5982	59.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8170	81.70%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	-	0.5832	58.32%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8379	83.79%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5739	57.39%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.4831	48.31%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7267	72.67%
Androgen receptor binding	+	0.5413	54.13%
Thyroid receptor binding	+	0.5923	59.23%
Glucocorticoid receptor binding	+	0.5505	55.05%
Aromatase binding	+	0.5465	54.65%
PPAR gamma	+	0.6226	62.26%
Honey bee toxicity	-	0.7013	70.13%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.8218	82.18%

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%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.14%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.11%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.54%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.86%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.77%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.94%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.40%	95.56%
CHEMBL3194	P02766	Transthyretin	88.77%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.15%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.78%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.96%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	85.82%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	85.64%	83.82%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.51%	95.78%
CHEMBL4208	P20618	Proteasome component C5	84.63%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.42%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.00%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.53%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	82.01%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.27%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.98%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	80.53%	95.93%

Plants that contains it

• Cyclopia intermedia

Cross-Links

• PubChem: 163011943
• LOTUS: LTS0069705
• wikiData: Q105030355