5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-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: aa82dff8-54f3-4920-992b-ead6c3745e4d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-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)OC)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)OC)O)O)O
• InChI: InChI=1S/C28H32O16/c1-9-18(32)22(36)26(27(38)40-9)41-11-6-13(31)17-15(7-11)42-24(10-3-4-12(30)14(5-10)39-2)25(20(17)34)44-28-23(37)21(35)19(33)16(8-29)43-28/h3-7,9,16,18-19,21-23,26-33,35-38H,8H2,1-2H3/t9-,16+,18-,19+,21-,22+,23+,26-,27-,28-/m1/s1
• InChI Key: WTANZOWRBNXICR-CFBFOJJCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₆
• Molecular Weight: 624.50 g/mol
• Exact Mass: 624.16903493 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.74
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.9113	91.13%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.5734	57.34%
OATP1B1 inhibitior	+	0.9049	90.49%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7557	75.57%
P-glycoprotein inhibitior	-	0.5088	50.88%
P-glycoprotein substrate	+	0.5197	51.97%
CYP3A4 substrate	+	0.6547	65.47%
CYP2C9 substrate	-	0.8457	84.57%
CYP2D6 substrate	-	0.8538	85.38%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.7950	79.50%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9060	90.60%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5829	58.29%
Human Ether-a-go-go-Related Gene inhibition	+	0.6652	66.52%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.7448	74.48%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9176	91.76%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.7857	78.57%
Androgen receptor binding	+	0.5272	52.72%
Thyroid receptor binding	-	0.5517	55.17%
Glucocorticoid receptor binding	+	0.6444	64.44%
Aromatase binding	-	0.5252	52.52%
PPAR gamma	+	0.6414	64.14%
Honey bee toxicity	-	0.7399	73.99%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5649	56.49%
Fish aquatic toxicity	+	0.7522	75.22%

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	99.03%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.15%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.72%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.43%	91.49%
CHEMBL2581	P07339	Cathepsin D	94.87%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.84%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.53%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.49%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.60%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.17%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.39%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.55%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.47%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.88%	96.21%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.29%	95.78%
CHEMBL3401	O75469	Pregnane X receptor	84.13%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.29%	96.00%
CHEMBL4208	P20618	Proteasome component C5	82.81%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.47%	94.45%
CHEMBL3194	P02766	Transthyretin	81.25%	90.71%
CHEMBL220	P22303	Acetylcholinesterase	80.16%	94.45%

Plants that contains it

• Reseda villosa

Cross-Links

• PubChem: 162888844
• LOTUS: LTS0127078
• wikiData: Q105312234