(2S)-2-(1-hydroxy-1-methyl-ethyl)-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,3-dihydrofuro[3,2-g]chromen-7-one

Details

• Internal ID: cc5e38f5-63e5-44c9-bd67-b2d7c42dbdb1
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 2-(2-hydroxypropan-2-yl)-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrofuro[3,2-g]chromen-7-one
• SMILES (Canonical): CC(C)(C1CC2=C(O1)C(=C3C(=C2)C=CC(=O)O3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): CC(C)(C1CC2=C(O1)C(=C3C(=C2)C=CC(=O)O3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C20H24O10/c1-20(2,26)11-6-9-5-8-3-4-12(22)29-16(8)18(17(9)28-11)30-19-15(25)14(24)13(23)10(7-21)27-19/h3-5,10-11,13-15,19,21,23-26H,6-7H2,1-2H3/t10-,11?,13-,14+,15-,19+/m1/s1
• InChI Key: JWWFVRMFYKPZNE-RINUOYIASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₁₀
• Molecular Weight: 424.40 g/mol
• Exact Mass: 424.13694696 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.95
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• C09309
• AC1L9CC2
• MolPort-001-741-093
• ZINC04098003
• (2S)-2-(1-hydroxy-1-methyl-ethyl)-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,3-dihydrofuro[3,2-g]chromen-7-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7702	77.02%
Caco-2	-	0.8139	81.39%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7568	75.68%
OATP2B1 inhibitior	-	0.8522	85.22%
OATP1B1 inhibitior	+	0.9011	90.11%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.8329	83.29%
P-glycoprotein inhibitior	-	0.6268	62.68%
P-glycoprotein substrate	-	0.8475	84.75%
CYP3A4 substrate	+	0.5771	57.71%
CYP2C9 substrate	-	0.8223	82.23%
CYP2D6 substrate	-	0.8518	85.18%
CYP3A4 inhibition	-	0.8892	88.92%
CYP2C9 inhibition	-	0.8680	86.80%
CYP2C19 inhibition	-	0.8343	83.43%
CYP2D6 inhibition	-	0.9033	90.33%
CYP1A2 inhibition	-	0.6932	69.32%
CYP2C8 inhibition	-	0.6916	69.16%
CYP inhibitory promiscuity	-	0.7011	70.11%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6246	62.46%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9090	90.90%
Skin irritation	-	0.7972	79.72%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6582	65.82%
Micronuclear	-	0.5467	54.67%
Hepatotoxicity	-	0.5447	54.47%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8129	81.29%
Acute Oral Toxicity (c)	III	0.6592	65.92%
Estrogen receptor binding	+	0.8259	82.59%
Androgen receptor binding	+	0.6316	63.16%
Thyroid receptor binding	+	0.5470	54.70%
Glucocorticoid receptor binding	+	0.6684	66.84%
Aromatase binding	+	0.6594	65.94%
PPAR gamma	+	0.7265	72.65%
Honey bee toxicity	-	0.8473	84.73%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9463	94.63%

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	98.65%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.35%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.34%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.97%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.96%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.16%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	88.46%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.24%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.87%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.41%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.05%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.13%	89.34%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.91%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.70%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.36%	92.62%
CHEMBL4208	P20618	Proteasome component C5	81.33%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.61%	96.95%

Plants that contains it

• Atalantia racemosa
• Boenninghausenia albiflora
• Kitagawia praeruptora
• Ruta graveolens
• Seseli grandivittatum

Cross-Links

• PubChem: 12315119
• NPASS: NPC237186
• LOTUS: LTS0043336
• wikiData: Q105136413