4-(3,4-Dihydroxyphenyl)-7-methoxy-5-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-2H-1-benzopyran-2-one

Details

• Internal ID: dd7e8a50-acb7-4924-a652-7ab5930d86f7
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 4-(3,4-dihydroxyphenyl)-7-methoxy-5-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): COC1=CC2=C(C(=CC(=O)O2)C3=CC(=C(C=C3)O)O)C(=C1)OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC2=C(C(=CC(=O)O2)C3=CC(=C(C=C3)O)O)C(=C1)OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-37-11-5-16-20(12(7-19(31)40-16)10-2-3-13(28)14(29)4-10)17(6-11)41-27-25(36)23(34)22(33)18(42-27)9-39-26-24(35)21(32)15(30)8-38-26/h2-7,15,18,21-30,32-36H,8-9H2,1H3
• InChI Key: GXDJGKMWLJOJFR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.48
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5869	58.69%
Caco-2	-	0.9073	90.73%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6520	65.20%
OATP2B1 inhibitior	-	0.7087	70.87%
OATP1B1 inhibitior	+	0.8940	89.40%
OATP1B3 inhibitior	+	0.9536	95.36%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6910	69.10%
P-glycoprotein inhibitior	-	0.6615	66.15%
P-glycoprotein substrate	-	0.5280	52.80%
CYP3A4 substrate	+	0.6468	64.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8494	84.94%
CYP3A4 inhibition	-	0.9412	94.12%
CYP2C9 inhibition	-	0.9439	94.39%
CYP2C19 inhibition	-	0.8989	89.89%
CYP2D6 inhibition	-	0.9172	91.72%
CYP1A2 inhibition	-	0.9037	90.37%
CYP2C8 inhibition	+	0.6941	69.41%
CYP inhibitory promiscuity	-	0.8756	87.56%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6679	66.79%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9172	91.72%
Skin irritation	-	0.8291	82.91%
Skin corrosion	-	0.9599	95.99%
Ames mutagenesis	+	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7240	72.40%
Micronuclear	+	0.6074	60.74%
Hepatotoxicity	-	0.8047	80.47%
skin sensitisation	-	0.9195	91.95%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9422	94.22%
Acute Oral Toxicity (c)	III	0.6736	67.36%
Estrogen receptor binding	+	0.8294	82.94%
Androgen receptor binding	+	0.6868	68.68%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4799	47.99%
Aromatase binding	+	0.5709	57.09%
PPAR gamma	+	0.7134	71.34%
Honey bee toxicity	-	0.7440	74.40%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6649	66.49%
Fish aquatic toxicity	+	0.8179	81.79%

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	99.70%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.07%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.74%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.32%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.03%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.72%	99.15%
CHEMBL220	P22303	Acetylcholinesterase	95.40%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.49%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.51%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.94%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.66%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.81%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	89.68%	83.82%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	89.43%	95.53%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.77%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.83%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.56%	95.89%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.26%	80.78%
CHEMBL226	P30542	Adenosine A1 receptor	86.12%	95.93%
CHEMBL4208	P20618	Proteasome component C5	85.32%	90.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.07%	96.77%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.98%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	84.85%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.30%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.54%	92.62%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.47%	95.78%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.44%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.34%	99.23%
CHEMBL1907	P15144	Aminopeptidase N	81.95%	93.31%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.83%	90.71%

Plants that contains it

• Coutarea hexandra
• Hintonia latiflora

Cross-Links

• PubChem: 14134096
• LOTUS: LTS0021533
• wikiData: Q105023018