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

Details

• Internal ID: d2b13d89-4abe-4f2f-9c80-a76ba8b5fe53
• 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,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1C(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): C1[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/C20H18O11/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/h1-5,12,15,17,20-26,28H,6H2/t12-,15-,17+,20+/m0/s1
• InChI Key: PZZRDJXEMZMZFD-JNEVDQRJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₁₁
• Molecular Weight: 434.30 g/mol
• Exact Mass: 434.08491139 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.10
• 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	-	0.8670	86.70%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5933	59.33%
OATP2B1 inhibitior	+	0.5893	58.93%
OATP1B1 inhibitior	+	0.9439	94.39%
OATP1B3 inhibitior	+	0.7973	79.73%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5164	51.64%
P-glycoprotein inhibitior	-	0.5481	54.81%
P-glycoprotein substrate	-	0.6956	69.56%
CYP3A4 substrate	+	0.6455	64.55%
CYP2C9 substrate	-	0.6831	68.31%
CYP2D6 substrate	-	0.8574	85.74%
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	+	0.8996	89.96%
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	-	0.7088	70.88%
Skin irritation	-	0.7662	76.62%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5363	53.63%
Micronuclear	+	0.7833	78.33%
Hepatotoxicity	+	0.5177	51.77%
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	-	0.9256	92.56%
Acute Oral Toxicity (c)	III	0.4631	46.31%
Estrogen receptor binding	+	0.7730	77.30%
Androgen receptor binding	+	0.8015	80.15%
Thyroid receptor binding	-	0.5328	53.28%
Glucocorticoid receptor binding	+	0.7132	71.32%
Aromatase binding	+	0.5692	56.92%
PPAR gamma	+	0.6902	69.02%
Honey bee toxicity	-	0.7070	70.70%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5450	54.50%
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	99.59%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.69%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.00%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.01%	99.15%
CHEMBL2581	P07339	Cathepsin D	92.76%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.92%	94.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	89.53%	96.12%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.76%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.89%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.86%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.43%	95.78%
CHEMBL3194	P02766	Transthyretin	86.95%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.73%	95.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.08%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.84%	86.33%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	85.22%	95.53%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.29%	99.23%
CHEMBL4208	P20618	Proteasome component C5	80.82%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.66%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.46%	96.09%

Plants that contains it

• Allium neapolitanum
• Amelanchier spicata
• Angelica taiwaniana
• Aster koraiensis
• Bellium bellidioides
• Centaurea calcitrapa
• Clutia lanceolata
• Cycas armstrongii
• Cycas revoluta
• Cynara humilis
• Dasiphora fruticosa
• Delphinium hohenackeri
• Dipodium squamatum
• Elegia deusta
• Ephedra aphylla
• Erica glauca
• Foeniculum vulgare
• Galium atherodes
• Garcinia intermedia
• Hydrocotyle leucocephala
• Hypericum perforatum
• Hypericum scabrum
• Jacobaea vulgaris
• Kielmeyera coriacea
• Kitagawia praeruptora
• Leucas neufliseana
• Licaria armeniaca
• Lithospermum officinale
• Litsea glutinosa
• Mammillaria magnimamma
• Munronia pinnata
• Oncosiphon suffruticosus
• Phoebe formosana
• Pilularia globulifera
• Platonia insignis
• Plectocephalus chilensis
• Plectranthus parishii
• Psittacanthus cucullaris
• Quercus suber
• Salvia munzii
• Sarcococca coriacea
• Solanum villosum
• Sophora koreensis
• Synotis cappa
• Tabebuia heterophylla
• Tephrosia vogelii
• Trachelospermum lucidum
• Trichilia hirta
• Typha domingensis
• Ulmus americana
• Wikstroemia chamaedaphne
• Wollastonia dentata
• Zanthoxylum bungeanum

Cross-Links

• PubChem: 5317847
• NPASS: NPC98143
• LOTUS: LTS0052031
• wikiData: Q105217269