(S)-3',5-Dihydroxy-4'-methoxy-7-[2-O,6-O-di(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]flavanone

Details

• Internal ID: afcc75b0-6caf-4f76-8f4f-2195ace87a0a
• 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-(3-hydroxy-4-methoxyphenyl)-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)OC)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)OC)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/C34H44O19/c1-11-23(38)26(41)29(44)32(48-11)47-10-21-25(40)28(43)31(53-33-30(45)27(42)24(39)12(2)49-33)34(52-21)50-14-7-16(36)22-17(37)9-19(51-20(22)8-14)13-4-5-18(46-3)15(35)6-13/h4-8,11-12,19,21,23-36,38-45H,9-10H2,1-3H3/t11-,12-,19-,21+,23-,24-,25+,26+,27+,28-,29+,30+,31+,32+,33-,34+/m0/s1
• InChI Key: LMWHBZYEUQWDBE-WDBBAESJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₄O₁₉
• Molecular Weight: 756.70 g/mol
• Exact Mass: 756.24767917 g/mol
• Topological Polar Surface Area (TPSA): 293.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.30
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

• (2S)-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-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
• (S)-3',5-Dihydroxy-4'-methoxy-7-[2-O,6-O-di(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]flavanone
• 97218-30-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4796	47.96%
Caco-2	-	0.8890	88.90%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6680	66.80%
OATP2B1 inhibitior	-	0.8606	86.06%
OATP1B1 inhibitior	+	0.9399	93.99%
OATP1B3 inhibitior	+	0.9137	91.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6897	68.97%
P-glycoprotein inhibitior	-	0.6352	63.52%
P-glycoprotein substrate	+	0.5621	56.21%
CYP3A4 substrate	+	0.6596	65.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	-	0.9310	93.10%
CYP2C9 inhibition	-	0.9351	93.51%
CYP2C19 inhibition	-	0.9301	93.01%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.9113	91.13%
CYP2C8 inhibition	+	0.6191	61.91%
CYP inhibitory promiscuity	-	0.6965	69.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6809	68.09%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9145	91.45%
Skin irritation	-	0.8382	83.82%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7570	75.70%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.9454	94.54%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.7862	78.62%
Acute Oral Toxicity (c)	III	0.6850	68.50%
Estrogen receptor binding	+	0.8100	81.00%
Androgen receptor binding	-	0.7232	72.32%
Thyroid receptor binding	+	0.5653	56.53%
Glucocorticoid receptor binding	+	0.5887	58.87%
Aromatase binding	-	0.4872	48.72%
PPAR gamma	+	0.7098	70.98%
Honey bee toxicity	-	0.6705	67.05%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.8533	85.33%

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	99.25%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.30%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.23%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.84%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.06%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.76%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.12%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.08%	95.89%
CHEMBL4208	P20618	Proteasome component C5	92.06%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.31%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.77%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.29%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	88.41%	91.49%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.62%	96.21%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.46%	94.80%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.11%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	84.82%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.33%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.25%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.94%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.85%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.49%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.73%	96.00%

Plants that contains it

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

Cross-Links

• PubChem: 102316658
• NPASS: NPC15049
• LOTUS: LTS0160534
• wikiData: Q105154162