3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-[(1S)-1-hydroxy-2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyethyl]oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

Details

• Internal ID: b9b2f1e3-6c44-4e13-b1c1-0ea9b7ecdc7d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-[(1S)-1-hydroxy-2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyethyl]oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC(C2C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)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]([C@@H]2[C@H]([C@@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-8-17(33)19(35)21(37)26(40-8)39-7-14(32)24-20(36)22(38)27(42-24)43-25-18(34)16-13(31)5-10(28)6-15(16)41-23(25)9-2-3-11(29)12(30)4-9/h2-6,8,14,17,19-22,24,26-33,35-38H,7H2,1H3/t8-,14+,17-,19+,20+,21+,22+,24-,26+,27+/m1/s1
• InChI Key: JMGZEFIQIZZSBH-YUUSATSASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.69
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7462	74.62%
Caco-2	-	0.9151	91.51%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7541	75.41%
OATP2B1 inhibitior	-	0.5603	56.03%
OATP1B1 inhibitior	+	0.9214	92.14%
OATP1B3 inhibitior	+	0.8970	89.70%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5719	57.19%
P-glycoprotein inhibitior	-	0.6123	61.23%
P-glycoprotein substrate	+	0.5392	53.92%
CYP3A4 substrate	+	0.6614	66.14%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.7513	75.13%
CYP2C9 inhibition	-	0.8169	81.69%
CYP2C19 inhibition	-	0.8322	83.22%
CYP2D6 inhibition	-	0.8540	85.40%
CYP1A2 inhibition	-	0.8317	83.17%
CYP2C8 inhibition	+	0.8631	86.31%
CYP inhibitory promiscuity	-	0.5352	53.52%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5590	55.90%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8874	88.74%
Skin irritation	-	0.8019	80.19%
Skin corrosion	-	0.9521	95.21%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7143	71.43%
Micronuclear	+	0.7392	73.92%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8817	88.17%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8740	87.40%
Acute Oral Toxicity (c)	III	0.6744	67.44%
Estrogen receptor binding	+	0.7649	76.49%
Androgen receptor binding	+	0.6688	66.88%
Thyroid receptor binding	+	0.5365	53.65%
Glucocorticoid receptor binding	+	0.5752	57.52%
Aromatase binding	+	0.5936	59.36%
PPAR gamma	+	0.6998	69.98%
Honey bee toxicity	-	0.7284	72.84%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.8860	88.60%

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	99.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.76%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.98%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.32%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.83%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.64%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	93.52%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.32%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.63%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.34%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.91%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	88.10%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.71%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.96%	97.09%
CHEMBL1900	P15121	Aldose reductase	83.45%	92.38%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.33%	95.64%
CHEMBL4208	P20618	Proteasome component C5	82.57%	90.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.45%	95.56%
CHEMBL3194	P02766	Transthyretin	82.29%	90.71%

Plants that contains it

• Ajania fruticulosa
• Artemisia biennis
• Artemisia dracunculus
• Tessaria fastigiata

Cross-Links

• PubChem: 163185343
• LOTUS: LTS0012025
• wikiData: Q105139222