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

Details

• Internal ID: debf8ec0-69ab-4bfc-93bb-108134b191e7
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 7-[6-[[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-(2,3-dihydroxy-3-methylbutyl)chromen-2-one
• SMILES (Canonical): CC(C)(C(CC1=C(C=C2C(=C1)C=CC(=O)O2)OC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O)O)O
• SMILES (Isomeric): CC(C)(C(CC1=C(C=C2C(=C1)C=CC(=O)O2)OC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C25H34O14/c1-24(2,33)16(27)6-12-5-11-3-4-17(28)37-13(11)7-14(12)38-22-20(31)19(30)18(29)15(39-22)8-35-23-21(32)25(34,9-26)10-36-23/h3-5,7,15-16,18-23,26-27,29-34H,6,8-10H2,1-2H3
• InChI Key: DVLIAXKBIVLBKD-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₁₄
• Molecular Weight: 558.50 g/mol
• Exact Mass: 558.19485575 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.89
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• 155740-16-2
• 7-[6-[[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-(2,3-dihydroxy-3-methylbutyl)chromen-2-one
• Peucedanol 7-O-beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside
• DTXSID00935282
• AKOS040735698
• 2H-1-Benzopyran-2-one, 7-((6-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy)-6-(2,3-dihydroxy-3-methylbutyl)-, (R)-
• 6-(2,3-Dihydroxy-3-methylbutyl)-2-oxo-2H-1-benzopyran-7-yl 6-O-[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7927	79.27%
Caco-2	-	0.8827	88.27%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7099	70.99%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8894	88.94%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8105	81.05%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.5132	51.32%
CYP3A4 substrate	+	0.6534	65.34%
CYP2C9 substrate	-	0.8139	81.39%
CYP2D6 substrate	-	0.8606	86.06%
CYP3A4 inhibition	-	0.9265	92.65%
CYP2C9 inhibition	-	0.9186	91.86%
CYP2C19 inhibition	-	0.8637	86.37%
CYP2D6 inhibition	-	0.8996	89.96%
CYP1A2 inhibition	-	0.7880	78.80%
CYP2C8 inhibition	+	0.5196	51.96%
CYP inhibitory promiscuity	-	0.8695	86.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6354	63.54%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9380	93.80%
Skin irritation	-	0.8052	80.52%
Skin corrosion	-	0.9470	94.70%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8240	82.40%
Micronuclear	-	0.5926	59.26%
Hepatotoxicity	-	0.5698	56.98%
skin sensitisation	-	0.8584	85.84%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6372	63.72%
Acute Oral Toxicity (c)	III	0.5659	56.59%
Estrogen receptor binding	+	0.7877	78.77%
Androgen receptor binding	+	0.5525	55.25%
Thyroid receptor binding	-	0.4887	48.87%
Glucocorticoid receptor binding	+	0.6598	65.98%
Aromatase binding	+	0.7449	74.49%
PPAR gamma	+	0.7370	73.70%
Honey bee toxicity	-	0.7376	73.76%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9464	94.64%

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	99.15%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.93%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	97.83%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.84%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.30%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.25%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.10%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.46%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.97%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.89%	99.23%
CHEMBL4581	P52732	Kinesin-like protein 1	88.75%	93.18%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.56%	96.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.49%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	88.39%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.89%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.93%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.08%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.75%	89.62%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.63%	97.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.58%	90.71%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.22%	95.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.18%	96.90%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.57%	96.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.55%	96.77%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.46%	94.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.28%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.07%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.36%	97.36%

Plants that contains it

• Peucedanum japonicum

Cross-Links

• PubChem: 197658
• LOTUS: LTS0165731
• wikiData: Q82911318