6-[(2S,3R,4S,5R)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one

Details

• Internal ID: e30cb088-c589-44ec-813c-afa55e001356
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 6-[(2S,3R,4S,5R)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)C4C(C(C(CO4)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)[C@H]4[C@@H]([C@H]([C@@H](CO4)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C28H32O14/c1-37-12-5-3-11(4-6-12)15-7-13(30)19-17(40-15)8-16(38-2)20(23(19)34)26-27(21(32)14(31)10-39-26)42-28-25(36)24(35)22(33)18(9-29)41-28/h3-8,14,18,21-22,24-29,31-36H,9-10H2,1-2H3/t14-,18-,21+,22-,24+,25-,26+,27-,28+/m1/s1
• InChI Key: URIBFXWZIUKTHQ-MLVDMZSRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₄
• Molecular Weight: 592.50 g/mol
• Exact Mass: 592.17920569 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.84
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8936	89.36%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5131	51.31%
OATP2B1 inhibitior	-	0.8418	84.18%
OATP1B1 inhibitior	+	0.7809	78.09%
OATP1B3 inhibitior	+	0.9648	96.48%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7448	74.48%
P-glycoprotein inhibitior	-	0.5536	55.36%
P-glycoprotein substrate	+	0.5433	54.33%
CYP3A4 substrate	+	0.6857	68.57%
CYP2C9 substrate	-	0.8389	83.89%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9256	92.56%
CYP2C9 inhibition	-	0.9546	95.46%
CYP2C19 inhibition	-	0.9465	94.65%
CYP2D6 inhibition	-	0.9421	94.21%
CYP1A2 inhibition	-	0.9248	92.48%
CYP2C8 inhibition	+	0.6536	65.36%
CYP inhibitory promiscuity	-	0.8563	85.63%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7040	70.40%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9343	93.43%
Skin irritation	-	0.8352	83.52%
Skin corrosion	-	0.9591	95.91%
Ames mutagenesis	+	0.6372	63.72%
Human Ether-a-go-go-Related Gene inhibition	+	0.7256	72.56%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.9283	92.83%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9762	97.62%
Acute Oral Toxicity (c)	III	0.7477	74.77%
Estrogen receptor binding	+	0.8700	87.00%
Androgen receptor binding	+	0.7640	76.40%
Thyroid receptor binding	+	0.5405	54.05%
Glucocorticoid receptor binding	+	0.6852	68.52%
Aromatase binding	+	0.6046	60.46%
PPAR gamma	+	0.7445	74.45%
Honey bee toxicity	-	0.7062	70.62%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.3639	36.39%

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	99.79%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.74%	85.14%
CHEMBL2581	P07339	Cathepsin D	98.02%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.85%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.88%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.37%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.11%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.12%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.71%	96.21%
CHEMBL220	P22303	Acetylcholinesterase	89.19%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.44%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.38%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.59%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.57%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.07%	99.15%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	86.03%	89.23%
CHEMBL4208	P20618	Proteasome component C5	85.42%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.66%	97.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.33%	95.83%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.60%	92.62%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.57%	83.57%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.55%	90.71%
CHEMBL2243	O00519	Anandamide amidohydrolase	81.77%	97.53%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.10%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.19%	99.17%

Plants that contains it

• Asterostigma riedelianum

Cross-Links

• PubChem: 162846240
• LOTUS: LTS0022958
• wikiData: Q105277790