5-[6-[[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-(3,4-dihydroxyphenyl)-7-hydroxychromen-2-one

Details

• Internal ID: 2ce1024b-a2b0-4b85-a592-331d357975c4
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 5-[6-[[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-(3,4-dihydroxyphenyl)-7-hydroxychromen-2-one
• SMILES (Canonical): C1C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=CC4=C3C(=CC(=O)O4)C5=CC(=C(C=C5)O)O)O)O)O)O)O)(CO)O
• SMILES (Isomeric): C1C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=CC4=C3C(=CC(=O)O4)C5=CC(=C(C=C5)O)O)O)O)O)O)O)(CO)O
• InChI: InChI=1S/C26H28O15/c27-8-26(36)9-38-25(23(26)35)37-7-17-20(32)21(33)22(34)24(41-17)40-16-5-11(28)4-15-19(16)12(6-18(31)39-15)10-1-2-13(29)14(30)3-10/h1-6,17,20-25,27-30,32-36H,7-9H2
• InChI Key: URQNORFSMLKGLE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₅
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.14282018 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.78
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6622	66.22%
Caco-2	-	0.9188	91.88%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6721	67.21%
OATP2B1 inhibitior	-	0.5638	56.38%
OATP1B1 inhibitior	+	0.9016	90.16%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7678	76.78%
P-glycoprotein inhibitior	-	0.5498	54.98%
P-glycoprotein substrate	-	0.5367	53.67%
CYP3A4 substrate	+	0.6670	66.70%
CYP2C9 substrate	-	0.8139	81.39%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.8530	85.30%
CYP2C9 inhibition	-	0.9230	92.30%
CYP2C19 inhibition	-	0.8294	82.94%
CYP2D6 inhibition	-	0.9000	90.00%
CYP1A2 inhibition	-	0.9163	91.63%
CYP2C8 inhibition	+	0.8162	81.62%
CYP inhibitory promiscuity	-	0.8529	85.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5862	58.62%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.8146	81.46%
Skin corrosion	-	0.9568	95.68%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6476	64.76%
Micronuclear	+	0.5774	57.74%
Hepatotoxicity	-	0.6518	65.18%
skin sensitisation	-	0.8779	87.79%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6610	66.10%
Acute Oral Toxicity (c)	III	0.5035	50.35%
Estrogen receptor binding	+	0.7748	77.48%
Androgen receptor binding	+	0.6842	68.42%
Thyroid receptor binding	+	0.5495	54.95%
Glucocorticoid receptor binding	+	0.5634	56.34%
Aromatase binding	+	0.6835	68.35%
PPAR gamma	+	0.7673	76.73%
Honey bee toxicity	-	0.6764	67.64%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.8637	86.37%

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	99.76%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	97.47%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.90%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.48%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.90%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.40%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.12%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.43%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	92.90%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.24%	86.33%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	91.51%	95.53%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.50%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.01%	99.23%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	89.89%	80.78%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.20%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.76%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.63%	95.78%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.04%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.68%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	85.61%	94.75%
CHEMBL4040	P28482	MAP kinase ERK2	84.75%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.51%	96.09%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	84.46%	96.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.04%	100.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.89%	83.00%
CHEMBL3194	P02766	Transthyretin	82.48%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.12%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.39%	92.94%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.23%	97.28%

Plants that contains it

• Coutarea hexandra

Cross-Links

• PubChem: 14134094
• LOTUS: LTS0152510
• wikiData: Q105277972