5-hydroxy-2-(4-hydroxyphenyl)-8-methoxy-3,7-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one

Details

• Internal ID: abc196e2-607d-4715-bb61-2e02f7975e0b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-8-methoxy-3,7-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• SMILES (Canonical): COC1=C(C=C(C2=C1OC(=C(C2=O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC=C(C=C4)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C2=C1OC(=C(C2=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC=C(C=C4)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C28H32O17/c1-40-24-12(41-27-21(38)19(36)16(33)13(7-29)42-27)6-11(32)15-18(35)26(23(44-25(15)24)9-2-4-10(31)5-3-9)45-28-22(39)20(37)17(34)14(8-30)43-28/h2-6,13-14,16-17,19-22,27-34,36-39H,7-8H2,1H3/t13-,14-,16-,17-,19+,20+,21-,22-,27-,28+/m1/s1
• InChI Key: CFIHXLIHVDSMJY-IJBXCHOPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₇
• Molecular Weight: 640.50 g/mol
• Exact Mass: 640.16394955 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -2.76
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.9134	91.34%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.5705	57.05%
OATP1B1 inhibitior	+	0.9078	90.78%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8652	86.52%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.6588	65.88%
CYP3A4 substrate	+	0.6018	60.18%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.7205	72.05%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9022	90.22%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5746	57.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7330	73.30%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6037	60.37%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.7919	79.19%
Androgen receptor binding	+	0.6320	63.20%
Thyroid receptor binding	-	0.5390	53.90%
Glucocorticoid receptor binding	+	0.5764	57.64%
Aromatase binding	+	0.5659	56.59%
PPAR gamma	+	0.6865	68.65%
Honey bee toxicity	-	0.7865	78.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.6698	66.98%

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	99.32%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.81%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.79%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.54%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.06%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.80%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.25%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.14%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.53%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.25%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.67%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.05%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.27%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.47%	96.21%
CHEMBL3194	P02766	Transthyretin	80.81%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.75%	95.89%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.43%	95.64%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.06%	95.78%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.05%	95.89%

Plants that contains it

• Sedum sarmentosum

Cross-Links

• PubChem: 102574415
• LOTUS: LTS0215087
• wikiData: Q104956583