2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 47f4be0e-1516-4202-9c34-d9d798da5717
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C20H20O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17-26,28H,6H2/t12-,15+,17-,18?,19?,20+/m1/s1
• InChI Key: UKSPRKDZNYSFRL-PXOCLKCNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₁₁
• Molecular Weight: 436.40 g/mol
• Exact Mass: 436.10056145 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.35
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6780	67.80%
Caco-2	-	0.8760	87.60%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5933	59.33%
OATP2B1 inhibitior	+	0.5757	57.57%
OATP1B1 inhibitior	+	0.9484	94.84%
OATP1B3 inhibitior	+	0.7973	79.73%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5850	58.50%
P-glycoprotein inhibitior	-	0.6939	69.39%
P-glycoprotein substrate	-	0.8648	86.48%
CYP3A4 substrate	+	0.6037	60.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8488	84.88%
CYP3A4 inhibition	-	0.9103	91.03%
CYP2C9 inhibition	-	0.9494	94.94%
CYP2C19 inhibition	-	0.9283	92.83%
CYP2D6 inhibition	-	0.9097	90.97%
CYP1A2 inhibition	-	0.9062	90.62%
CYP2C8 inhibition	+	0.5091	50.91%
CYP inhibitory promiscuity	-	0.9169	91.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6637	66.37%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.6708	67.08%
Skin irritation	-	0.7662	76.62%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4679	46.79%
Micronuclear	+	0.7833	78.33%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8965	89.65%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6997	69.97%
Acute Oral Toxicity (c)	III	0.4631	46.31%
Estrogen receptor binding	+	0.7610	76.10%
Androgen receptor binding	+	0.6242	62.42%
Thyroid receptor binding	+	0.5175	51.75%
Glucocorticoid receptor binding	+	0.6383	63.83%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6352	63.52%
Honey bee toxicity	-	0.7596	75.96%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.8495	84.95%

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	99.69%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.44%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.91%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.66%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.52%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.91%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.91%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.45%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.42%	98.95%
CHEMBL2535	P11166	Glucose transporter	86.64%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.27%	94.45%
CHEMBL4208	P20618	Proteasome component C5	84.62%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.51%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.98%	86.33%
CHEMBL3194	P02766	Transthyretin	81.72%	90.71%

Plants that contains it

• Acer glabrum
• Alchornea cordifolia
• Artabotrys hexapetalus
• Asplenium viride
• Bergenia crassifolia
• Betula pendula
• Calluna vulgaris
• Chamaebatia foliolosa
• Cistus laurifolius
• Crossopteryx febrifuga
• Diplusodon astictus
• Erythroxylum pruinosum
• Erythroxylum ulei
• Eucalyptus consideniana
• Eucalyptus ovata
• Fallopia convolvulus
• Fuchsia boliviana
• Fuchsia paniculata
• Haematoxylum campechianum
• Hypericum androsaemum
• Hypericum erectum
• Hypericum perforatum
• Illicium difengpi
• Lathyrus pratensis
• Licania pittieri
• Moquilea pyrifolia
• Norantea guianensis
• Oenothera speciosa
• Parinari congensis
• Phlebodium aureum
• Polylepis incana
• Psidium guajava
• Pyrola chlorantha
• Rhododendron simsii
• Rosa gallica
• Sarracenia flava
• Senegalia polyacantha
• Stevia rebaudiana
• Stevia suaveolens
• Theobroma cacao
• Trachelospermum jasminoides
• Urospermum dalechampii
• Vaccinium macrocarpon
• Zanthoxylum bungeanum

Cross-Links

• PubChem: 5317364
• LOTUS: LTS0135293
• wikiData: Q105274879