3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxolan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one

Details

• Internal ID: 1f5172b7-4ea2-405e-b0a1-78ac68fef84a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxolan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC(=C(C2=O)OC3C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)C5=CC(=C(C=C5)O)OC)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC(=C(C2=O)O[C@H]3[C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)C5=CC(=C(C=C5)O)OC)O
• InChI: InChI=1S/C28H32O16/c1-38-11-6-13(31)18-15(7-11)41-25(10-3-4-12(30)14(5-10)39-2)26(21(18)34)44-28-23(36)20(33)17(43-28)9-40-27-24(37)22(35)19(32)16(8-29)42-27/h3-7,16-17,19-20,22-24,27-33,35-37H,8-9H2,1-2H3/t16-,17-,19-,20-,22+,23+,24-,27-,28+/m1/s1
• InChI Key: JXRZMKWWELOXOG-RYDBIISISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₆
• Molecular Weight: 624.50 g/mol
• Exact Mass: 624.16903493 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.47
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5738	57.38%
Caco-2	-	0.9065	90.65%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6853	68.53%
OATP2B1 inhibitior	-	0.5796	57.96%
OATP1B1 inhibitior	+	0.9048	90.48%
OATP1B3 inhibitior	+	0.9658	96.58%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5931	59.31%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.5881	58.81%
CYP3A4 substrate	+	0.6350	63.50%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.8249	82.49%
CYP2C9 inhibition	-	0.8289	82.89%
CYP2C19 inhibition	-	0.7821	78.21%
CYP2D6 inhibition	-	0.9289	92.89%
CYP1A2 inhibition	-	0.9073	90.73%
CYP2C8 inhibition	+	0.8243	82.43%
CYP inhibitory promiscuity	+	0.5201	52.01%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6193	61.93%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.8405	84.05%
Skin corrosion	-	0.9559	95.59%
Ames mutagenesis	-	0.5128	51.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4393	43.93%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	-	0.6573	65.73%
skin sensitisation	-	0.8944	89.44%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7817	78.17%
Acute Oral Toxicity (c)	III	0.7581	75.81%
Estrogen receptor binding	+	0.8401	84.01%
Androgen receptor binding	+	0.6283	62.83%
Thyroid receptor binding	+	0.5150	51.50%
Glucocorticoid receptor binding	+	0.6144	61.44%
Aromatase binding	+	0.5936	59.36%
PPAR gamma	+	0.7141	71.41%
Honey bee toxicity	-	0.7863	78.63%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.7803	78.03%

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	99.15%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.00%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.13%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.10%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.46%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.31%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.09%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.12%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.24%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.96%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.84%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	89.16%	94.73%
CHEMBL220	P22303	Acetylcholinesterase	88.90%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.54%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.09%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.29%	96.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.83%	95.78%
CHEMBL4208	P20618	Proteasome component C5	82.83%	90.00%
CHEMBL3194	P02766	Transthyretin	80.84%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.51%	92.62%

Plants that contains it

• Retama sphaerocarpa

Cross-Links

• PubChem: 162845162
• LOTUS: LTS0157219
• wikiData: Q105136757