2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	3cb5221a-313e-408e-8ecf-75e50fbcf8f9
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
IUPAC Name	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
SMILES (Canonical)	CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
SMILES (Isomeric)	C[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
InChI	InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m1/s1
InChI Key	OXGUCUVFOIWWQJ-JHPRLSDPSA-N
Popularity	6 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₁H₂₀O₁₁
Molecular Weight	448.40 g/mol
Exact Mass	448.10056145 g/mol
Topological Polar Surface Area (TPSA)	186.00 Å²
XlogP	0.90
Atomic LogP (AlogP)	0.49
H-Bond Acceptor	11
H-Bond Donor	7
Rotatable Bonds	3

Synonyms

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SCHEMBL2290545

CHEMBL2262641

BDBM50129557

J3.637.493D

2-(3,4-Dihydroxyphenyl)-3-(alpha-D-rhamnopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one

InChI=1/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m1/s

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8357	83.57%
Caco-2	-	0.7858	78.58%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7163	71.63%
OATP2B1 inhibitior	+	0.5902	59.02%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9188	91.88%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6264	62.64%
P-glycoprotein inhibitior	-	0.5351	53.51%
P-glycoprotein substrate	-	0.6786	67.86%
CYP3A4 substrate	+	0.6264	62.64%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.7109	71.09%
CYP2C9 inhibition	-	0.8538	85.38%
CYP2C19 inhibition	-	0.8339	83.39%
CYP2D6 inhibition	-	0.9547	95.47%
CYP1A2 inhibition	-	0.5306	53.06%
CYP2C8 inhibition	+	0.9061	90.61%
CYP inhibitory promiscuity	-	0.5648	56.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.7424	74.24%
Skin irritation	-	0.6220	62.20%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	+	0.5863	58.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.6352	63.52%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8874	88.74%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8191	81.91%
Acute Oral Toxicity (c)	III	0.5184	51.84%
Estrogen receptor binding	+	0.6589	65.89%
Androgen receptor binding	+	0.7443	74.43%
Thyroid receptor binding	+	0.5667	56.67%
Glucocorticoid receptor binding	+	0.7217	72.17%
Aromatase binding	-	0.5140	51.40%
PPAR gamma	+	0.6941	69.41%
Honey bee toxicity	-	0.7943	79.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5050	50.50%
Fish aquatic toxicity	+	0.9457	94.57%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1900	P15121	Aldose reductase	150 nM	IC50	via Super-PRED
CHEMBL205	P00918	Carbonic anhydrase II	6367.7 nM	Ki	PMID: 26498393
CHEMBL3729	P22748	Carbonic anhydrase IV	67.3 nM 67.3 nM	Ki Ki	PMID: 26498393 via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	3.9 nM 3.9 nM	Ki Ki	PMID: 26498393 via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	43.5 nM 43.5 nM	Ki Ki	PMID: 26498393 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.27%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.14%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.95%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.65%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.47%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.04%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	92.01%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.54%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.50%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.82%	95.56%
CHEMBL3194	P02766	Transthyretin	87.42%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.11%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.55%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.06%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.30%	95.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.11%	99.23%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.02%	93.65%
CHEMBL4208	P20618	Proteasome component C5	82.43%	90.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.26%	80.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.95%	97.36%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Abies lasiocarpa var. lasiocarpa

Caralluma stalagmifera