3-hydroxy-2-(7-hydroxy-1,3-benzodioxol-5-yl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: dbb4838b-11dc-4e3b-ac0f-033a44f3fb46
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-hydroxy-2-(7-hydroxy-1,3-benzodioxol-5-yl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1OC2=CC(=CC(=C2O1)O)C3=C(C(=O)C4=C(O3)C=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C1OC2=CC(=CC(=C2O1)O)C3=C(C(=O)C4=C(O3)C=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C22H20O12/c23-6-14-16(26)17(27)19(29)22(34-14)32-9-1-2-10-12(5-9)33-20(18(28)15(10)25)8-3-11(24)21-13(4-8)30-7-31-21/h1-5,14,16-17,19,22-24,26-29H,6-7H2/t14-,16-,17+,19-,22-/m1/s1
• InChI Key: LTOSTBGJHNIWGF-XQUDQRHWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₁₂
• Molecular Weight: 476.40 g/mol
• Exact Mass: 476.09547607 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.22
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5949	59.49%
Caco-2	-	0.9381	93.81%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6301	63.01%
OATP2B1 inhibitior	-	0.5508	55.08%
OATP1B1 inhibitior	+	0.9401	94.01%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6027	60.27%
P-glycoprotein inhibitior	-	0.5509	55.09%
P-glycoprotein substrate	-	0.6906	69.06%
CYP3A4 substrate	+	0.6398	63.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8415	84.15%
CYP3A4 inhibition	-	0.5780	57.80%
CYP2C9 inhibition	-	0.8821	88.21%
CYP2C19 inhibition	-	0.7756	77.56%
CYP2D6 inhibition	-	0.8441	84.41%
CYP1A2 inhibition	-	0.8878	88.78%
CYP2C8 inhibition	+	0.5889	58.89%
CYP inhibitory promiscuity	+	0.5366	53.66%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5924	59.24%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8703	87.03%
Skin irritation	-	0.8047	80.47%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3975	39.75%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8767	87.67%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8260	82.60%
Acute Oral Toxicity (c)	III	0.5647	56.47%
Estrogen receptor binding	+	0.7232	72.32%
Androgen receptor binding	+	0.6280	62.80%
Thyroid receptor binding	+	0.5191	51.91%
Glucocorticoid receptor binding	-	0.4681	46.81%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7778	77.78%
Honey bee toxicity	-	0.7356	73.56%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8350	83.50%

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	99.92%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.98%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.19%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.08%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.61%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.89%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.33%	94.45%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	94.04%	83.57%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.58%	99.15%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.08%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.19%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.70%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.70%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	87.27%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.71%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.62%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.63%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.41%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.19%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.15%	96.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.02%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.48%	100.00%

Plants that contains it

• Cydonia oblonga

Cross-Links

• PubChem: 10576557
• LOTUS: LTS0021450
• wikiData: Q105157078