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

Details

• Internal ID: 58a6c087-71f6-4e41-8927-6de6d2e6ea37
• 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-methoxychromen-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(CO5)(CO)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(CO5)(CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-37-12-5-16-20(13(7-19(31)40-16)11-2-3-14(29)15(30)4-11)17(6-12)41-25-23(34)22(33)21(32)18(42-25)8-38-26-24(35)27(36,9-28)10-39-26/h2-7,18,21-26,28-30,32-36H,8-10H2,1H3
• InChI Key: KNCNSYQYJUBLPW-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: -1.60
• Atomic LogP (AlogP): -1.48
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• 5-[6-[[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-(3,4-dihydroxyphenyl)-7-methoxychromen-2-one
• Compound NP-002740
• MEGxp0_000948
• ACon1_000707
• CHEBI:189136
• AKOS040739938
• BRD-A72694303-001-01-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6999	69.99%
Caco-2	-	0.9014	90.14%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6762	67.62%
OATP2B1 inhibitior	-	0.5801	58.01%
OATP1B1 inhibitior	+	0.8955	89.55%
OATP1B3 inhibitior	+	0.9628	96.28%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7222	72.22%
P-glycoprotein inhibitior	-	0.5174	51.74%
P-glycoprotein substrate	+	0.5132	51.32%
CYP3A4 substrate	+	0.6723	67.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8541	85.41%
CYP3A4 inhibition	-	0.8688	86.88%
CYP2C9 inhibition	-	0.8938	89.38%
CYP2C19 inhibition	-	0.8148	81.48%
CYP2D6 inhibition	-	0.9092	90.92%
CYP1A2 inhibition	-	0.9115	91.15%
CYP2C8 inhibition	+	0.7517	75.17%
CYP inhibitory promiscuity	-	0.8358	83.58%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5632	56.32%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9170	91.70%
Skin irritation	-	0.8179	81.79%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6720	67.20%
Micronuclear	+	0.5774	57.74%
Hepatotoxicity	-	0.7571	75.71%
skin sensitisation	-	0.8789	87.89%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7828	78.28%
Acute Oral Toxicity (c)	III	0.6243	62.43%
Estrogen receptor binding	+	0.8353	83.53%
Androgen receptor binding	+	0.7037	70.37%
Thyroid receptor binding	+	0.5375	53.75%
Glucocorticoid receptor binding	+	0.6447	64.47%
Aromatase binding	+	0.6564	65.64%
PPAR gamma	+	0.7506	75.06%
Honey bee toxicity	-	0.7273	72.73%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.7753	77.53%

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	99.78%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.43%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.97%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.22%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.96%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.22%	89.00%
CHEMBL220	P22303	Acetylcholinesterase	95.05%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	94.08%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.43%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.38%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.01%	86.33%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	91.03%	95.53%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.25%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.28%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.32%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.36%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.23%	96.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.98%	97.36%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.58%	96.95%
CHEMBL1907	P15144	Aminopeptidase N	85.27%	93.31%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.93%	80.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.73%	85.14%
CHEMBL4208	P20618	Proteasome component C5	83.95%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.93%	92.94%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.17%	97.28%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.12%	92.62%
CHEMBL1951	P21397	Monoamine oxidase A	80.70%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	80.70%	94.73%

Plants that contains it

• Hintonia latiflora

Cross-Links

• PubChem: 23983728
• LOTUS: LTS0092761
• wikiData: Q104170433