7-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one

Details

• Internal ID: f37a74d9-1500-4eda-b720-f1ea5a4d2870
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)COC5C(C(C(O5)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-37-16-4-10(2-3-12(16)29)15-7-14(31)20-13(30)5-11(6-17(20)40-15)39-27-25(36)23(34)22(33)19(42-27)9-38-26-24(35)21(32)18(8-28)41-26/h2-7,18-19,21-30,32-36H,8-9H2,1H3/t18-,19-,21-,22-,23+,24-,25-,26-,27-/m1/s1
• InChI Key: WGQZBBOLNCUXLC-OVYGZGMLSA-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): 234.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.48
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5974	59.74%
Caco-2	-	0.9225	92.25%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6848	68.48%
OATP2B1 inhibitior	-	0.5683	56.83%
OATP1B1 inhibitior	+	0.9252	92.52%
OATP1B3 inhibitior	+	0.9746	97.46%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6923	69.23%
P-glycoprotein inhibitior	-	0.6844	68.44%
P-glycoprotein substrate	+	0.5303	53.03%
CYP3A4 substrate	+	0.5774	57.74%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.8638	86.38%
CYP2C9 inhibition	-	0.8003	80.03%
CYP2C19 inhibition	-	0.7529	75.29%
CYP2D6 inhibition	-	0.9197	91.97%
CYP1A2 inhibition	-	0.8921	89.21%
CYP2C8 inhibition	+	0.7582	75.82%
CYP inhibitory promiscuity	+	0.5065	50.65%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5707	57.07%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9221	92.21%
Skin irritation	-	0.8306	83.06%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	-	0.5492	54.92%
Human Ether-a-go-go-Related Gene inhibition	+	0.7284	72.84%
Micronuclear	+	0.6833	68.33%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.8970	89.70%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7686	76.86%
Acute Oral Toxicity (c)	III	0.7481	74.81%
Estrogen receptor binding	+	0.7966	79.66%
Androgen receptor binding	+	0.5653	56.53%
Thyroid receptor binding	-	0.5302	53.02%
Glucocorticoid receptor binding	-	0.4679	46.79%
Aromatase binding	+	0.5972	59.72%
PPAR gamma	+	0.7226	72.26%
Honey bee toxicity	-	0.7171	71.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.7431	74.31%

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	99.32%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.55%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.83%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.59%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.51%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.50%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.95%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.54%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.23%	86.33%
CHEMBL220	P22303	Acetylcholinesterase	91.84%	94.45%
CHEMBL3194	P02766	Transthyretin	89.61%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.04%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.20%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.24%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.93%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.18%	96.21%
CHEMBL1907	P15144	Aminopeptidase N	85.10%	93.31%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.87%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.41%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.25%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.42%	97.36%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.76%	96.00%

Plants that contains it

• Phlomis nissolii

Cross-Links

• PubChem: 162969049
• LOTUS: LTS0067815
• wikiData: Q105304822