5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-7-hydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: fb24fc3f-fa26-41c3-b956-b2e5be119a6b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-7-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=CC4=C3C(=O)C=C(O4)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=CC4=C3C(=O)C=C(O4)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)39-17-7-13(30)6-16-19(17)14(31)8-15(38-16)11-2-4-12(29)5-3-11/h2-8,10,18,20-30,32-36H,9H2,1H3/t10-,18-,20-,21-,22+,23+,24+,25-,26-,27-/m1/s1
• InChI Key: LYKXPTCUGPKDQL-FLPYCHHVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₄
• Molecular Weight: 578.50 g/mol
• Exact Mass: 578.16355563 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.10
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5182	51.82%
Caco-2	-	0.9182	91.82%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7093	70.93%
OATP2B1 inhibitior	-	0.7000	70.00%
OATP1B1 inhibitior	+	0.8752	87.52%
OATP1B3 inhibitior	+	0.9637	96.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6299	62.99%
P-glycoprotein inhibitior	-	0.7377	73.77%
P-glycoprotein substrate	-	0.5484	54.84%
CYP3A4 substrate	+	0.6381	63.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8471	84.71%
CYP3A4 inhibition	-	0.9373	93.73%
CYP2C9 inhibition	-	0.9390	93.90%
CYP2C19 inhibition	-	0.9490	94.90%
CYP2D6 inhibition	-	0.9615	96.15%
CYP1A2 inhibition	-	0.9095	90.95%
CYP2C8 inhibition	+	0.6990	69.90%
CYP inhibitory promiscuity	-	0.7369	73.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6533	65.33%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9191	91.91%
Skin irritation	-	0.8247	82.47%
Skin corrosion	-	0.9664	96.64%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4162	41.62%
Micronuclear	+	0.6133	61.33%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9405	94.05%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8411	84.11%
Acute Oral Toxicity (c)	III	0.6229	62.29%
Estrogen receptor binding	+	0.7891	78.91%
Androgen receptor binding	+	0.6633	66.33%
Thyroid receptor binding	+	0.5840	58.40%
Glucocorticoid receptor binding	+	0.6333	63.33%
Aromatase binding	+	0.6549	65.49%
PPAR gamma	+	0.7522	75.22%
Honey bee toxicity	-	0.6711	67.11%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.7844	78.44%

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	98.96%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.33%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.02%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.76%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.12%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	93.90%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.66%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.44%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	90.44%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.72%	97.36%
CHEMBL3194	P02766	Transthyretin	88.94%	90.71%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	88.70%	83.57%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.22%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.34%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.10%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.94%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.20%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.25%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	81.86%	98.35%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.50%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.65%	95.89%

Plants that contains it

• Carallia brachiata

Cross-Links

• PubChem: 163087831
• LOTUS: LTS0241356
• wikiData: Q105159407