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

Details

• Internal ID: 5998a66a-598a-4975-8d07-3c2ea1a4f35f
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 5,6-dihydroxy-2-methyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(C(=C4C(=C3)OC(=CC4=O)C)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(C(=C4C(=C3)OC(=CC4=O)C)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C22H28O14/c1-6-3-8(23)12-9(33-6)4-10(14(25)16(12)27)35-22-20(31)18(29)15(26)11(36-22)5-32-21-19(30)17(28)13(24)7(2)34-21/h3-4,7,11,13,15,17-22,24-31H,5H2,1-2H3/t7-,11+,13-,15+,17+,18-,19+,20+,21+,22+/m0/s1
• InChI Key: JYIVYVFUUKYCSU-GCCWPOOFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₁₄
• Molecular Weight: 516.40 g/mol
• Exact Mass: 516.14790556 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.46
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

• 2-Methyl-5,6-dihydroxy-7-[6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5504	55.04%
Caco-2	-	0.8743	87.43%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6923	69.23%
OATP2B1 inhibitior	-	0.5723	57.23%
OATP1B1 inhibitior	+	0.7900	79.00%
OATP1B3 inhibitior	+	0.9261	92.61%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6451	64.51%
P-glycoprotein inhibitior	-	0.7914	79.14%
P-glycoprotein substrate	-	0.5885	58.85%
CYP3A4 substrate	+	0.5930	59.30%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.8810	88.10%
CYP2C9 inhibition	-	0.9243	92.43%
CYP2C19 inhibition	-	0.9041	90.41%
CYP2D6 inhibition	-	0.9239	92.39%
CYP1A2 inhibition	-	0.8109	81.09%
CYP2C8 inhibition	-	0.6026	60.26%
CYP inhibitory promiscuity	-	0.7614	76.14%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7079	70.79%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9277	92.77%
Skin irritation	-	0.8211	82.11%
Skin corrosion	-	0.9625	96.25%
Ames mutagenesis	-	0.5064	50.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.6631	66.31%
Micronuclear	+	0.6692	66.92%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9123	91.23%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9218	92.18%
Acute Oral Toxicity (c)	III	0.6677	66.77%
Estrogen receptor binding	+	0.6778	67.78%
Androgen receptor binding	-	0.5169	51.69%
Thyroid receptor binding	+	0.5207	52.07%
Glucocorticoid receptor binding	+	0.5785	57.85%
Aromatase binding	+	0.6070	60.70%
PPAR gamma	+	0.6271	62.71%
Honey bee toxicity	-	0.7931	79.31%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.8962	89.62%

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	98.53%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	96.40%	94.73%
CHEMBL2581	P07339	Cathepsin D	96.14%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.98%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.22%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.82%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	93.23%	91.49%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.84%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.14%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.92%	86.92%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.72%	89.34%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.05%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.70%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.64%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.37%	90.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.16%	96.90%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.07%	95.64%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.71%	95.89%

Plants that contains it

• Crossosoma bigelovii

Cross-Links

• PubChem: 44139363
• NPASS: NPC181616
• ChEMBL: CHEMBL562227
• LOTUS: LTS0272957
• wikiData: Q105137052