8-[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one

Details

• Internal ID: 4c78d75f-bb35-4b9f-9901-37adb403f747
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=C(C2=C(C(=C1)O)C(=O)C=C(O2)C3=CC=C(C=C3)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(C(CO5)O)O)O
• SMILES (Isomeric): COC1=C(C2=C(C(=C1)O)C(=O)C=C(O2)C3=CC=C(C=C3)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](CO5)O)O)O
• InChI: InChI=1S/C27H30O14/c1-37-16-7-13(31)18-12(30)6-15(10-2-4-11(29)5-3-10)39-24(18)19(16)25-26(22(35)21(34)17(8-28)40-25)41-27-23(36)20(33)14(32)9-38-27/h2-7,14,17,20-23,25-29,31-36H,8-9H2,1H3/t14-,17-,20+,21+,22-,23+,25-,26+,27+/m0/s1
• InChI Key: YQIWCUKZIPUVPY-KISRDTOPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₄
• Molecular Weight: 578.50 g/mol
• Exact Mass: 578.16355563 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.14
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4761	47.61%
Caco-2	-	0.9028	90.28%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5114	51.14%
OATP2B1 inhibitior	-	0.7076	70.76%
OATP1B1 inhibitior	+	0.8446	84.46%
OATP1B3 inhibitior	+	0.9679	96.79%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8710	87.10%
P-glycoprotein inhibitior	-	0.5924	59.24%
P-glycoprotein substrate	+	0.5084	50.84%
CYP3A4 substrate	+	0.6718	67.18%
CYP2C9 substrate	-	0.8389	83.89%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9417	94.17%
CYP2C9 inhibition	-	0.9488	94.88%
CYP2C19 inhibition	-	0.9370	93.70%
CYP2D6 inhibition	-	0.9411	94.11%
CYP1A2 inhibition	-	0.9224	92.24%
CYP2C8 inhibition	+	0.6816	68.16%
CYP inhibitory promiscuity	-	0.8596	85.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6677	66.77%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9321	93.21%
Skin irritation	-	0.8242	82.42%
Skin corrosion	-	0.9582	95.82%
Ames mutagenesis	+	0.6536	65.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.3747	37.47%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9265	92.65%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8534	85.34%
Acute Oral Toxicity (c)	III	0.7135	71.35%
Estrogen receptor binding	+	0.8384	83.84%
Androgen receptor binding	+	0.7692	76.92%
Thyroid receptor binding	+	0.5354	53.54%
Glucocorticoid receptor binding	+	0.6419	64.19%
Aromatase binding	+	0.6225	62.25%
PPAR gamma	+	0.7361	73.61%
Honey bee toxicity	-	0.6973	69.73%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.4193	41.93%

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	99.43%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.63%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.23%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.49%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.28%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.32%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.31%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.56%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.86%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.44%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.87%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.69%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.33%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.15%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.88%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.49%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.84%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.61%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.26%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.60%	97.28%
CHEMBL3401	O75469	Pregnane X receptor	81.30%	94.73%

Plants that contains it

• Deschampsia antarctica

Cross-Links

• PubChem: 163060359
• LOTUS: LTS0001605
• wikiData: Q105352236