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

Details

• Internal ID: b773a707-4b3d-495c-a8c9-424ea5ef78ab
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)OC)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=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)OC)CO)O)O)O)O)O
• InChI: InChI=1S/C28H32O15/c1-10-18(32)21(35)23(37)27(39-10)43-26-22(36)19(33)16(9-29)41-28(26)42-25-20(34)17-14(31)7-12(30)8-15(17)40-24(25)11-3-5-13(38-2)6-4-11/h3-8,10,16,18-19,21-23,26-33,35-37H,9H2,1-2H3/t10-,16+,18-,19+,21+,22-,23+,26+,27-,28-/m0/s1
• InChI Key: BZRYTCVZZLOPIO-SNVRNOIASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₅
• Molecular Weight: 608.50 g/mol
• Exact Mass: 608.17412031 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.09
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.9118	91.18%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.7090	70.90%
OATP1B1 inhibitior	+	0.8861	88.61%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8841	88.41%
P-glycoprotein inhibitior	-	0.6112	61.12%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6683	66.83%
CYP2C9 substrate	-	0.8740	87.40%
CYP2D6 substrate	-	0.8547	85.47%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.7792	77.92%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9180	91.80%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5337	53.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7224	72.24%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9089	90.89%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8504	85.04%
Androgen receptor binding	+	0.6720	67.20%
Thyroid receptor binding	+	0.5527	55.27%
Glucocorticoid receptor binding	+	0.6264	62.64%
Aromatase binding	+	0.5753	57.53%
PPAR gamma	+	0.7200	72.00%
Honey bee toxicity	-	0.7447	74.47%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7522	75.22%

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	99.67%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.12%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	96.85%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.31%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.21%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.60%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.02%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.69%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.63%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.53%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.65%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.57%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	90.48%	94.73%
CHEMBL4208	P20618	Proteasome component C5	89.91%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.54%	85.14%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.04%	95.64%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.96%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.70%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.57%	97.09%

Plants that contains it

• Costus spicatus

Cross-Links

• PubChem: 101022694
• LOTUS: LTS0047917
• wikiData: Q104950661