5-hydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one

Details

• Internal ID: aca00c56-11df-4e0b-9273-62b39f28a22e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)OC6C(C(C(C(O6)CO)O)O)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C33H42O19/c1-11-22(37)25(40)28(43)31(47-11)46-10-20-24(39)27(42)30(45)33(52-20)49-14-6-15(35)21-16(36)8-17(50-18(21)7-14)12-2-4-13(5-3-12)48-32-29(44)26(41)23(38)19(9-34)51-32/h2-7,11,17,19-20,22-35,37-45H,8-10H2,1H3/t11-,17?,19+,20+,22-,23+,24+,25+,26-,27-,28+,29+,30+,31+,32+,33+/m0/s1
• InChI Key: KQUWJUNIYQVHCG-ZLYYXHNSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₂O₁₉
• Molecular Weight: 742.70 g/mol
• Exact Mass: 742.23202911 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -3.69
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

• LMPK12140253
• 2-[4-(beta-D-Glucopyranosyloxy)phenyl]-7-[6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]-5-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5372	53.72%
Caco-2	-	0.8926	89.26%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6684	66.84%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.9327	93.27%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8842	88.42%
P-glycoprotein inhibitior	-	0.4890	48.90%
P-glycoprotein substrate	-	0.6783	67.83%
CYP3A4 substrate	+	0.6359	63.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8479	84.79%
CYP3A4 inhibition	-	0.9550	95.50%
CYP2C9 inhibition	-	0.9252	92.52%
CYP2C19 inhibition	-	0.9129	91.29%
CYP2D6 inhibition	-	0.9613	96.13%
CYP1A2 inhibition	-	0.8948	89.48%
CYP2C8 inhibition	+	0.4840	48.40%
CYP inhibitory promiscuity	-	0.6991	69.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6759	67.59%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9129	91.29%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8143	81.43%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.9289	92.89%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6305	63.05%
Acute Oral Toxicity (c)	III	0.5567	55.67%
Estrogen receptor binding	+	0.7918	79.18%
Androgen receptor binding	-	0.6230	62.30%
Thyroid receptor binding	-	0.4929	49.29%
Glucocorticoid receptor binding	-	0.4917	49.17%
Aromatase binding	+	0.5389	53.89%
PPAR gamma	+	0.7444	74.44%
Honey bee toxicity	-	0.7430	74.30%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.8024	80.24%

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	99.66%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.64%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.27%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.26%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.64%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.07%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.87%	94.00%
CHEMBL4208	P20618	Proteasome component C5	91.64%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.87%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.77%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.75%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.55%	94.73%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.06%	94.80%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.34%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.47%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.36%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.33%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	85.13%	95.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.05%	99.23%

Plants that contains it

• Citrus maxima

Cross-Links

• PubChem: 25080021
• NPASS: NPC73652