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

Details

• Internal ID: 047d611d-09e0-4542-84eb-38deb5e687f8
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-methyloxan-3-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)O)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)CO)O)O)O)C5=CC=C(C=C5)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC2=CC(=C3C(=C2)OC(=C(C3=O)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O)C5=CC=C(C=C5)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-9-17(31)21(35)25(26(37)38-9)39-12-6-13(30)16-14(7-12)40-23(10-2-4-11(29)5-3-10)24(19(16)33)42-27-22(36)20(34)18(32)15(8-28)41-27/h2-7,9,15,17-18,20-22,25-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20-,21+,22+,25-,26-,27-/m1/s1
• InChI Key: CZQIIQOHWPMHTC-WSEGJXNRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.74
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9174	91.74%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5585	55.85%
OATP1B1 inhibitior	+	0.8857	88.57%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8010	80.10%
P-glycoprotein inhibitior	-	0.5279	52.79%
P-glycoprotein substrate	-	0.5476	54.76%
CYP3A4 substrate	+	0.6469	64.69%
CYP2C9 substrate	-	0.8457	84.57%
CYP2D6 substrate	-	0.8538	85.38%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.7495	74.95%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8953	89.53%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5963	59.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.6703	67.03%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8795	87.95%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7467	74.67%
Androgen receptor binding	+	0.6298	62.98%
Thyroid receptor binding	-	0.5284	52.84%
Glucocorticoid receptor binding	+	0.5728	57.28%
Aromatase binding	-	0.5137	51.37%
PPAR gamma	+	0.6937	69.37%
Honey bee toxicity	-	0.7601	76.01%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.8289	82.89%

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	99.01%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.58%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.44%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.95%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.56%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.07%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.94%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.63%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	90.38%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.88%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.94%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.56%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.49%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.34%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.13%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.03%	95.78%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.47%	96.21%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.71%	94.80%
CHEMBL242	Q92731	Estrogen receptor beta	80.80%	98.35%
CHEMBL4208	P20618	Proteasome component C5	80.37%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.25%	94.45%

Plants that contains it

• Reseda duriaeana

Cross-Links

• PubChem: 162948316
• LOTUS: LTS0015159
• wikiData: Q104972979