[(2R,3S,4S,5R,6S)-6-[4-(3,4-dihydroxyphenyl)-7-hydroxy-2-oxochromen-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: d6c2a7f9-c312-4b1f-b45b-52476c45bee7
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[4-(3,4-dihydroxyphenyl)-7-hydroxy-2-oxochromen-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2=CC(=CC3=C2C(=CC(=O)O3)C4=CC(=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC(=CC3=C2C(=CC(=O)O3)C4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C23H22O12/c1-9(24)32-8-17-20(29)21(30)22(31)23(35-17)34-16-6-11(25)5-15-19(16)12(7-18(28)33-15)10-2-3-13(26)14(27)4-10/h2-7,17,20-23,25-27,29-31H,8H2,1H3/t17-,20-,21+,22-,23-/m1/s1
• InChI Key: YHQLUSZEFHCADG-LDBVRRDLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₁₂
• Molecular Weight: 490.40 g/mol
• Exact Mass: 490.11112613 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.33
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5759	57.59%
Caco-2	-	0.8971	89.71%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6926	69.26%
OATP2B1 inhibitior	-	0.5481	54.81%
OATP1B1 inhibitior	+	0.8884	88.84%
OATP1B3 inhibitior	+	0.9515	95.15%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8237	82.37%
P-glycoprotein inhibitior	-	0.5765	57.65%
P-glycoprotein substrate	-	0.7151	71.51%
CYP3A4 substrate	+	0.6276	62.76%
CYP2C9 substrate	-	0.8113	81.13%
CYP2D6 substrate	-	0.8745	87.45%
CYP3A4 inhibition	-	0.9505	95.05%
CYP2C9 inhibition	-	0.9129	91.29%
CYP2C19 inhibition	-	0.9233	92.33%
CYP2D6 inhibition	-	0.9603	96.03%
CYP1A2 inhibition	-	0.8935	89.35%
CYP2C8 inhibition	+	0.7942	79.42%
CYP inhibitory promiscuity	-	0.8491	84.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7134	71.34%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8815	88.15%
Skin irritation	-	0.8133	81.33%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4544	45.44%
Micronuclear	+	0.5892	58.92%
Hepatotoxicity	-	0.7267	72.67%
skin sensitisation	-	0.9339	93.39%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7169	71.69%
Acute Oral Toxicity (c)	III	0.5815	58.15%
Estrogen receptor binding	+	0.7851	78.51%
Androgen receptor binding	+	0.7352	73.52%
Thyroid receptor binding	-	0.5054	50.54%
Glucocorticoid receptor binding	+	0.7212	72.12%
Aromatase binding	-	0.5633	56.33%
PPAR gamma	+	0.6040	60.40%
Honey bee toxicity	-	0.7512	75.12%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6599	65.99%
Fish aquatic toxicity	+	0.9613	96.13%

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	99.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.28%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	97.86%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.54%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	95.52%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.44%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.94%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.72%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.69%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.27%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.93%	95.78%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.77%	99.15%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.83%	96.95%
CHEMBL220	P22303	Acetylcholinesterase	87.10%	94.45%
CHEMBL3194	P02766	Transthyretin	86.88%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.57%	80.78%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.07%	95.64%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.90%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.82%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.61%	85.14%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.39%	83.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.42%	95.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.56%	97.21%

Plants that contains it

• Hintonia latiflora

Cross-Links

• PubChem: 102366249
• LOTUS: LTS0000284
• wikiData: Q105348562