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

Details

• Internal ID: 69a44a59-5983-458e-839b-d0d366dea677
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 5-hydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)O)C2COC3=CC(=C(C(=C3C2=O)O)OC)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)O)C2COC3=CC(=C(C(=C3C2=O)O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C24H28O13/c1-32-13-5-9(4-11(26)22(13)33-2)10-8-35-12-6-14(23(34-3)19(29)16(12)17(10)27)36-24-21(31)20(30)18(28)15(7-25)37-24/h4-6,10,15,18,20-21,24-26,28-31H,7-8H2,1-3H3/t10?,15-,18-,20+,21-,24-/m1/s1
• InChI Key: KGPMDDCBIHPQHZ-GRJMWHAUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₃
• Molecular Weight: 524.50 g/mol
• Exact Mass: 524.15299094 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.34
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5613	56.13%
Caco-2	-	0.8334	83.34%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5797	57.97%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.8715	87.15%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4705	47.05%
P-glycoprotein inhibitior	-	0.5268	52.68%
P-glycoprotein substrate	-	0.7286	72.86%
CYP3A4 substrate	+	0.6174	61.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8517	85.17%
CYP3A4 inhibition	-	0.9607	96.07%
CYP2C9 inhibition	-	0.9318	93.18%
CYP2C19 inhibition	-	0.9294	92.94%
CYP2D6 inhibition	-	0.9608	96.08%
CYP1A2 inhibition	-	0.9319	93.19%
CYP2C8 inhibition	+	0.5544	55.44%
CYP inhibitory promiscuity	-	0.7425	74.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6863	68.63%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9053	90.53%
Skin irritation	-	0.8525	85.25%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5372	53.72%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9360	93.60%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8300	83.00%
Acute Oral Toxicity (c)	III	0.7015	70.15%
Estrogen receptor binding	+	0.8025	80.25%
Androgen receptor binding	-	0.4879	48.79%
Thyroid receptor binding	+	0.5490	54.90%
Glucocorticoid receptor binding	+	0.5790	57.90%
Aromatase binding	-	0.5401	54.01%
PPAR gamma	+	0.6366	63.66%
Honey bee toxicity	-	0.8265	82.65%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.7238	72.38%

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	99.62%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.39%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	97.69%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.67%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.04%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.36%	94.00%
CHEMBL2581	P07339	Cathepsin D	91.69%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.53%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.87%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.33%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.90%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.85%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.74%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.07%	100.00%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	85.82%	92.68%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.43%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.52%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.10%	92.62%
CHEMBL4208	P20618	Proteasome component C5	82.81%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.01%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.86%	86.92%

Plants that contains it

• Iris domestica

Cross-Links

• PubChem: 101778643
• NPASS: NPC151864