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

Details

• Internal ID: f8b83b49-e165-4df6-8004-59066970e490
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3,5-dihydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O)C4=CC=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O)C4=CC=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-9-17(30)20(33)23(36)26(38-9)40-12-6-13(29)16-14(7-12)41-25(22(35)19(16)32)10-2-4-11(5-3-10)39-27-24(37)21(34)18(31)15(8-28)42-27/h2-7,9,15,17-18,20-21,23-24,26-31,33-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,23-,24+,26-,27+/m0/s1
• InChI Key: FYZRTNFFTKNBKH-LCCWYPFGSA-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	-	0.9009	90.09%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5562	55.62%
OATP1B1 inhibitior	+	0.9072	90.72%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6574	65.74%
P-glycoprotein inhibitior	-	0.5117	51.17%
P-glycoprotein substrate	-	0.5995	59.95%
CYP3A4 substrate	+	0.6297	62.97%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
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	+	0.7785	77.85%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9051	90.51%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5599	55.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.7309	73.09%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9376	93.76%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7266	72.66%
Androgen receptor binding	+	0.5569	55.69%
Thyroid receptor binding	-	0.5082	50.82%
Glucocorticoid receptor binding	-	0.4688	46.88%
Aromatase binding	+	0.5932	59.32%
PPAR gamma	+	0.7504	75.04%
Honey bee toxicity	-	0.7811	78.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5650	56.50%
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	99.63%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.97%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.77%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.15%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.95%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.87%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.06%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.20%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.57%	86.92%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.26%	95.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.08%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.01%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.48%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.24%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.43%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.67%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.22%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.17%	90.71%
CHEMBL3194	P02766	Transthyretin	80.44%	90.71%
CHEMBL4208	P20618	Proteasome component C5	80.11%	90.00%

Plants that contains it

• Pteridium aquilinum

Cross-Links

• PubChem: 163031453
• LOTUS: LTS0047717
• wikiData: Q105004816