2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 73ebe73a-8a12-4d29-ab7c-403118a61cf2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC(=C(C2=O)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O)C5=CC(=C(C=C5)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC(=C(C2=O)O[C@@H]3[C@H]([C@@H]([C@@H]([C@@H](O3)CO[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)O)O)C5=CC(=C(C=C5)O)O)O
• InChI: InChI=1S/C28H32O17/c1-40-10-5-13(32)17-14(6-10)42-25(9-2-3-11(30)12(31)4-9)26(20(17)35)45-28-24(39)22(37)19(34)16(44-28)8-41-27-23(38)21(36)18(33)15(7-29)43-27/h2-6,15-16,18-19,21-24,27-34,36-39H,7-8H2,1H3/t15-,16+,18+,19-,21+,22-,23-,24+,27-,28-/m1/s1
• InChI Key: VVNAVFMRGMPHSJ-OQLPSISJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₇
• Molecular Weight: 640.50 g/mol
• Exact Mass: 640.16394955 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.41
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.9225	92.25%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.5734	57.34%
OATP1B1 inhibitior	+	0.9162	91.62%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5649	56.49%
P-glycoprotein inhibitior	-	0.5367	53.67%
P-glycoprotein substrate	-	0.6268	62.68%
CYP3A4 substrate	+	0.6357	63.57%
CYP2C9 substrate	-	0.8415	84.15%
CYP2D6 substrate	-	0.8515	85.15%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.8127	81.27%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9062	90.62%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6858	68.58%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6073	60.73%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8060	80.60%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8184	81.84%
Androgen receptor binding	+	0.6482	64.82%
Thyroid receptor binding	+	0.5134	51.34%
Glucocorticoid receptor binding	-	0.4715	47.15%
Aromatase binding	+	0.5912	59.12%
PPAR gamma	+	0.7139	71.39%
Honey bee toxicity	-	0.7751	77.51%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.6698	66.98%

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	99.63%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.76%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.42%	99.15%
CHEMBL2581	P07339	Cathepsin D	95.79%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.98%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.67%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.07%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.76%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.17%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.84%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.90%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.85%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.97%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.99%	86.92%
CHEMBL1951	P21397	Monoamine oxidase A	86.85%	91.49%
CHEMBL4208	P20618	Proteasome component C5	82.51%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.44%	96.00%

Plants that contains it

• Senna septemtrionalis

Cross-Links

• PubChem: 163024549
• LOTUS: LTS0275362
• wikiData: Q105297732