(2R)-8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

Details

• Internal ID: da87e8e5-0bd0-4c4a-a8da-a192c1e2b564
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: (2R)-8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2C3=C4C(=C(C=C3O)O)C(=O)CC(O4)C5=CC=C(C=C5)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2C3=C4C(=C(C=C3O)O)C(=O)C[C@@H](O4)C5=CC=C(C=C5)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H32O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-6,9,15-16,19-23,25-31,33-37H,7-8H2,1H3/t9-,15+,16+,19-,20+,21+,22-,23+,25-,26+,27-/m0/s1
• InChI Key: LCTOQECBRZFOCD-MXWZVQRBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₄
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.17920569 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.12
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 5

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	-	0.9134	91.34%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.9429	94.29%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.8486	84.86%
OATP1B1 inhibitior	+	0.8627	86.27%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7086	70.86%
P-glycoprotein inhibitior	-	0.7241	72.41%
P-glycoprotein substrate	-	0.6839	68.39%
CYP3A4 substrate	+	0.6461	64.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8502	85.02%
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	+	0.5298	52.98%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9131	91.31%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5299	52.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.6595	65.95%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6201	62.01%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.8007	80.07%
Androgen receptor binding	+	0.6333	63.33%
Thyroid receptor binding	+	0.5341	53.41%
Glucocorticoid receptor binding	+	0.5951	59.51%
Aromatase binding	+	0.5566	55.66%
PPAR gamma	+	0.7032	70.32%
Honey bee toxicity	-	0.7468	74.68%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	99.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.39%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.58%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.54%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.44%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.71%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.41%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.61%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.65%	94.00%
CHEMBL4208	P20618	Proteasome component C5	86.50%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.94%	96.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.26%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.11%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	81.98%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.70%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.65%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.53%	97.36%

Plants that contains it

• Eriobotrya japonica

Cross-Links

• PubChem: 10507459
• LOTUS: LTS0010702
• wikiData: Q105149981