Naringenin 7-O-(2'',6''-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside

Details

• Internal ID: d31422d2-38fe-4fcb-80e9-c79d6c929977
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-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)O)O)OC6C(C(C(C(O6)C)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)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)O[C@H]6[C@@H]([C@@H]([C@H]([C@@H](O6)C)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C33H42O18/c1-11-22(37)25(40)28(43)31(46-11)45-10-20-24(39)27(42)30(51-32-29(44)26(41)23(38)12(2)47-32)33(50-20)48-15-7-16(35)21-17(36)9-18(49-19(21)8-15)13-3-5-14(34)6-4-13/h3-8,11-12,18,20,22-35,37-44H,9-10H2,1-2H3/t11-,12-,18-,20+,22-,23-,24+,25+,26+,27-,28+,29+,30+,31+,32-,33+/m0/s1
• InChI Key: BRDVWIOUHLWIGN-WWFYINPHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₂O₁₈
• Molecular Weight: 726.70 g/mol
• Exact Mass: 726.23711449 g/mol
• Topological Polar Surface Area (TPSA): 284.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.31
• H-Bond Acceptor: 18
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
• 4H-1-benzopyran-4-one, 7-[[O-6-deoxy-.alpha.-L-mannopyranosyl-(1-->2)-O-[6-deoxy-.alpha.-L-mannopyranosyl-(1-->6)]-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-
• 7-[2-O,6-O-Bis(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]-2alpha-(4-hydroxyphenyl)-5-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4659	46.59%
Caco-2	-	0.8967	89.67%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7552	75.52%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9358	93.58%
OATP1B3 inhibitior	+	0.9107	91.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6512	65.12%
P-glycoprotein inhibitior	-	0.6894	68.94%
P-glycoprotein substrate	-	0.5760	57.60%
CYP3A4 substrate	+	0.6542	65.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	-	0.8904	89.04%
CYP2C9 inhibition	-	0.9134	91.34%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.8713	87.13%
CYP2C8 inhibition	+	0.5465	54.65%
CYP inhibitory promiscuity	-	0.6602	66.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7067	70.67%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9157	91.57%
Skin irritation	-	0.8277	82.77%
Skin corrosion	-	0.9610	96.10%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7050	70.50%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.9381	93.81%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.7481	74.81%
Acute Oral Toxicity (c)	III	0.6245	62.45%
Estrogen receptor binding	+	0.7865	78.65%
Androgen receptor binding	-	0.5838	58.38%
Thyroid receptor binding	+	0.5421	54.21%
Glucocorticoid receptor binding	+	0.5556	55.56%
Aromatase binding	-	0.5073	50.73%
PPAR gamma	+	0.7231	72.31%
Honey bee toxicity	-	0.7026	70.26%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5450	54.50%
Fish aquatic toxicity	+	0.9179	91.79%

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	99.59%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.01%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.33%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.25%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.22%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.64%	86.33%
CHEMBL4208	P20618	Proteasome component C5	91.70%	90.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.48%	94.80%
CHEMBL3401	O75469	Pregnane X receptor	91.18%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.78%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.89%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.19%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.66%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.93%	99.15%
CHEMBL226	P30542	Adenosine A1 receptor	84.87%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.16%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.98%	96.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.60%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.70%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	80.55%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.49%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.38%	86.92%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.16%	85.00%

Plants that contains it

• Asterolasia squamuligera
• Catharanthus roseus
• Cinnamomum chekiangense
• Citrus medica
• Moringa oleifera
• Pluchea dioscoridis
• Pyrola rotundifolia
• Stevia alpina

Cross-Links

• PubChem: 5278403
• NPASS: NPC185414
• LOTUS: LTS0000770
• wikiData: Q104944740