7,8-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-2-one

Details

• Internal ID: 6a22ac64-d1de-4a20-9a07-f7cdd24bd807
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 7,8-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): C1=CC(=O)OC2=C(C(=CC(=C21)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=O)OC2=C(C(=CC(=C21)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C21H26O15/c22-4-9-13(26)15(28)17(30)20(34-9)32-5-10-14(27)16(29)18(31)21(35-10)33-8-3-7(23)12(25)19-6(8)1-2-11(24)36-19/h1-3,9-10,13-18,20-23,25-31H,4-5H2/t9-,10-,13-,14-,15+,16+,17-,18-,20-,21-/m1/s1
• InChI Key: JFLCQZNAJDFYPX-DWBJODBPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₁₅
• Molecular Weight: 518.40 g/mol
• Exact Mass: 518.12717012 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -3.79
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6547	65.47%
Caco-2	-	0.9301	93.01%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5154	51.54%
OATP2B1 inhibitior	-	0.5660	56.60%
OATP1B1 inhibitior	+	0.8794	87.94%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5952	59.52%
P-glycoprotein inhibitior	-	0.7926	79.26%
P-glycoprotein substrate	-	0.8054	80.54%
CYP3A4 substrate	+	0.5321	53.21%
CYP2C9 substrate	-	0.8151	81.51%
CYP2D6 substrate	-	0.8579	85.79%
CYP3A4 inhibition	-	0.9408	94.08%
CYP2C9 inhibition	-	0.9449	94.49%
CYP2C19 inhibition	-	0.8867	88.67%
CYP2D6 inhibition	-	0.9271	92.71%
CYP1A2 inhibition	-	0.9114	91.14%
CYP2C8 inhibition	+	0.4522	45.22%
CYP inhibitory promiscuity	-	0.8330	83.30%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6753	67.53%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9127	91.27%
Skin irritation	-	0.8240	82.40%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4369	43.69%
Micronuclear	+	0.5833	58.33%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8840	88.40%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8405	84.05%
Acute Oral Toxicity (c)	IV	0.4356	43.56%
Estrogen receptor binding	+	0.7479	74.79%
Androgen receptor binding	+	0.5622	56.22%
Thyroid receptor binding	+	0.5606	56.06%
Glucocorticoid receptor binding	-	0.4873	48.73%
Aromatase binding	+	0.7177	71.77%
PPAR gamma	+	0.7344	73.44%
Honey bee toxicity	-	0.8124	81.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6649	66.49%
Fish aquatic toxicity	+	0.7488	74.88%

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	99.73%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.37%	94.00%
CHEMBL220	P22303	Acetylcholinesterase	92.23%	94.45%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.39%	83.57%
CHEMBL2581	P07339	Cathepsin D	90.78%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.62%	89.00%
CHEMBL3194	P02766	Transthyretin	90.41%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.90%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.21%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.50%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	86.45%	94.73%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.31%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.77%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.83%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.89%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.46%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.13%	96.00%

Plants that contains it

• Tetraphis pellucida

Cross-Links

• PubChem: 101923603
• LOTUS: LTS0065705
• wikiData: Q105126727