2-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]-3,5,7-trihydroxychromen-4-one

Details

• Internal ID: 08278698-d9be-4a58-bd24-6b6a4a63a0d5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 2-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]-3,5,7-trihydroxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C27H30O16/c28-7-14-17(32)20(35)23(38)26(41-14)43-25-21(36)18(33)15(8-29)42-27(25)39-11-3-1-9(2-4-11)24-22(37)19(34)16-12(31)5-10(30)6-13(16)40-24/h1-6,14-15,17-18,20-21,23,25-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,23-,25-,26+,27-/m1/s1
• InChI Key: LKCFMVKTPNASKS-KWERPHBTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.42
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9282	92.82%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5623	56.23%
OATP1B1 inhibitior	+	0.8881	88.81%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.4649	46.49%
P-glycoprotein inhibitior	-	0.6007	60.07%
P-glycoprotein substrate	-	0.6587	65.87%
CYP3A4 substrate	+	0.6598	65.98%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.8570	85.70%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9118	91.18%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7372	73.72%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9059	90.59%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7851	78.51%
Androgen receptor binding	+	0.6402	64.02%
Thyroid receptor binding	-	0.4888	48.88%
Glucocorticoid receptor binding	-	0.5812	58.12%
Aromatase binding	+	0.6719	67.19%
PPAR gamma	+	0.7879	78.79%
Honey bee toxicity	-	0.6987	69.87%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.72%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.71%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	96.29%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.26%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.90%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.64%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.83%	99.15%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	92.15%	83.57%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.18%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.71%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.54%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.25%	86.92%
CHEMBL3194	P02766	Transthyretin	89.69%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.77%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.89%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.12%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.74%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.24%	95.56%
CHEMBL1929	P47989	Xanthine dehydrogenase	83.23%	96.12%
CHEMBL4208	P20618	Proteasome component C5	82.98%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.51%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.54%	96.09%

Plants that contains it

• Evolvulus alsinoides

Cross-Links

• PubChem: 71720752
• LOTUS: LTS0101009
• wikiData: Q105152973