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

Details

• Internal ID: 9b78a8f8-430e-47aa-a9ea-34c8a0dfa7d6
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 4-(3-hydroxy-4-methoxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=CC(=O)OC3=C2C(=CC(=C3)OC)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=CC(=O)OC3=C2C(=CC(=C3)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C23H24O11/c1-30-11-6-15-19(12(8-18(26)32-15)10-3-4-14(31-2)13(25)5-10)16(7-11)33-23-22(29)21(28)20(27)17(9-24)34-23/h3-8,17,20-25,27-29H,9H2,1-2H3/t17-,20-,21+,22-,23-/m1/s1
• InChI Key: FYSYTMFBANOLPM-LDBVRRDLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₁₁
• Molecular Weight: 476.40 g/mol
• Exact Mass: 476.13186158 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.36
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.8250	82.50%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.6980	69.80%
OATP1B1 inhibitior	+	0.9085	90.85%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5986	59.86%
P-glycoprotein inhibitior	-	0.5826	58.26%
P-glycoprotein substrate	-	0.6948	69.48%
CYP3A4 substrate	+	0.5944	59.44%
CYP2C9 substrate	-	0.8239	82.39%
CYP2D6 substrate	-	0.8498	84.98%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.7220	72.20%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9011	90.11%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4629	46.29%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.7946	79.46%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7879	78.79%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.7312	73.12%
Androgen receptor binding	+	0.6738	67.38%
Thyroid receptor binding	+	0.5162	51.62%
Glucocorticoid receptor binding	+	0.6983	69.83%
Aromatase binding	+	0.6011	60.11%
PPAR gamma	+	0.6142	61.42%
Honey bee toxicity	-	0.7709	77.09%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6649	66.49%
Fish aquatic toxicity	+	0.7522	75.22%

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	97.90%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.75%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.44%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.01%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.15%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.08%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.85%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.15%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.86%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	89.62%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.50%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.04%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.39%	95.78%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	86.72%	95.53%
CHEMBL3401	O75469	Pregnane X receptor	84.69%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.61%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.57%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.63%	95.50%
CHEMBL3194	P02766	Transthyretin	81.88%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.26%	97.09%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.15%	92.38%

Plants that contains it

• Hintonia latiflora

Cross-Links

• PubChem: 16091571
• LOTUS: LTS0083686
• wikiData: Q105004700