4-[(2R,3S,4R,5R,6S)-6-[[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-methylchromen-2-one

Details

• Internal ID: b00fc68e-7669-46c6-9621-59e3ce4e1764
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 4-[(2R,3S,4R,5R,6S)-6-[[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-methylchromen-2-one
• SMILES (Canonical): CC1=C2C(=CC=C1)OC(=O)C=C2OC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O
• SMILES (Isomeric): CC1=C2C(=CC=C1)OC(=O)C=C2O[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO[C@@H]4[C@H]([C@@](CO4)(CO)O)O)O)O)O
• InChI: InChI=1S/C21H26O12/c1-9-3-2-4-10-14(9)11(5-13(23)31-10)32-19-17(26)16(25)15(24)12(33-19)6-29-20-18(27)21(28,7-22)8-30-20/h2-5,12,15-20,22,24-28H,6-8H2,1H3/t12-,15-,16+,17-,18+,19-,20-,21-/m0/s1
• InChI Key: UQDQFRQJERKTJN-WPRKPFGHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₁₂
• Molecular Weight: 470.40 g/mol
• Exact Mass: 470.14242626 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -2.25
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5805	58.05%
Caco-2	-	0.8622	86.22%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6747	67.47%
OATP2B1 inhibitior	-	0.8478	84.78%
OATP1B1 inhibitior	+	0.9177	91.77%
OATP1B3 inhibitior	+	0.9595	95.95%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5925	59.25%
P-glycoprotein inhibitior	-	0.6586	65.86%
P-glycoprotein substrate	-	0.6269	62.69%
CYP3A4 substrate	+	0.6427	64.27%
CYP2C9 substrate	-	0.8212	82.12%
CYP2D6 substrate	-	0.8709	87.09%
CYP3A4 inhibition	-	0.9222	92.22%
CYP2C9 inhibition	-	0.9438	94.38%
CYP2C19 inhibition	-	0.8689	86.89%
CYP2D6 inhibition	-	0.9157	91.57%
CYP1A2 inhibition	-	0.9078	90.78%
CYP2C8 inhibition	+	0.4768	47.68%
CYP inhibitory promiscuity	-	0.8764	87.64%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5451	54.51%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9469	94.69%
Skin irritation	-	0.8165	81.65%
Skin corrosion	-	0.9577	95.77%
Ames mutagenesis	+	0.5346	53.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.3761	37.61%
Micronuclear	-	0.5126	51.26%
Hepatotoxicity	-	0.5893	58.93%
skin sensitisation	-	0.8764	87.64%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7147	71.47%
Acute Oral Toxicity (c)	III	0.5796	57.96%
Estrogen receptor binding	+	0.8453	84.53%
Androgen receptor binding	+	0.5735	57.35%
Thyroid receptor binding	+	0.5686	56.86%
Glucocorticoid receptor binding	+	0.6614	66.14%
Aromatase binding	+	0.7296	72.96%
PPAR gamma	+	0.7841	78.41%
Honey bee toxicity	-	0.8359	83.59%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7978	79.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	99.81%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.12%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.39%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.10%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.61%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.34%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.18%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.97%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.72%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	92.33%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.68%	99.23%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.07%	96.95%
CHEMBL226	P30542	Adenosine A1 receptor	88.91%	95.93%
CHEMBL1937	Q92769	Histone deacetylase 2	86.86%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.63%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.55%	97.21%
CHEMBL4581	P52732	Kinesin-like protein 1	85.44%	93.18%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.98%	100.00%
CHEMBL4302	P08183	P-glycoprotein 1	83.16%	92.98%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.14%	96.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.11%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.85%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.03%	96.21%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.80%	95.83%
CHEMBL4530	P00488	Coagulation factor XIII	80.65%	96.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.43%	96.39%

Plants that contains it

• Diospyros crassiflora

Cross-Links

• PubChem: 162856531
• LOTUS: LTS0097943
• wikiData: Q105277181