5-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 15ba6be0-f1ce-43ed-9a72-e4de0db875e5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4C([C@H]([C@@H](C(O4)CO)O)O)O)O
• InChI: InChI=1S/C23H24O12/c1-31-15-3-9(4-16(32-2)19(15)27)13-7-12(26)18-11(25)5-10(6-14(18)34-13)33-23-22(30)21(29)20(28)17(8-24)35-23/h3-7,17,20-25,27-30H,8H2,1-2H3/t17?,20-,21+,22?,23-/m1/s1
• InChI Key: JGXFMIJHKASCIZ-YFNQFTQVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₁₂
• Molecular Weight: 492.40 g/mol
• Exact Mass: 492.12677620 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.07
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• LMPK12110860

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.8781	87.81%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.5520	55.20%
OATP1B1 inhibitior	+	0.9285	92.85%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5664	56.64%
P-glycoprotein inhibitior	-	0.5222	52.22%
P-glycoprotein substrate	-	0.6291	62.91%
CYP3A4 substrate	+	0.5717	57.17%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.6144	61.44%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9096	90.96%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	+	0.5036	50.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.6564	65.64%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8341	83.41%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.7382	73.82%
Androgen receptor binding	+	0.5923	59.23%
Thyroid receptor binding	+	0.5581	55.81%
Glucocorticoid receptor binding	+	0.5771	57.71%
Aromatase binding	+	0.5529	55.29%
PPAR gamma	+	0.7121	71.21%
Honey bee toxicity	-	0.7077	70.77%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6949	69.49%
Fish aquatic toxicity	+	0.7522	75.22%

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	99.36%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.54%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.07%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.47%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.74%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.59%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.48%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.00%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.87%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.40%	95.56%
CHEMBL3194	P02766	Transthyretin	88.17%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.74%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	86.72%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.69%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.57%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.43%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.22%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.99%	90.71%
CHEMBL220	P22303	Acetylcholinesterase	81.73%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.37%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.04%	95.89%

Plants that contains it

• Hyparrhenia hirta
• Saccharum officinarum
• Sedum sarmentosum
• Setaria italica

Cross-Links

• PubChem: 44258267
• NPASS: NPC147301
• LOTUS: LTS0239428
• wikiData: Q104395975