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

Details

• Internal ID: 4a50509d-8f1a-4951-894c-d9dada0a2bfc
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O)C5=CC(=C(C(=C5)O)O)O)OC6C(C(C(C(O6)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C5=CC(=C(C(=C5)O)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O
• InChI: InChI=1S/C33H40O22/c1-8-18(39)25(46)30(55-32-27(48)24(45)21(42)16(7-35)53-32)33(49-8)54-29-22(43)17-11(36)4-10(50-31-26(47)23(44)20(41)15(6-34)52-31)5-14(17)51-28(29)9-2-12(37)19(40)13(38)3-9/h2-5,8,15-16,18,20-21,23-27,30-42,44-48H,6-7H2,1H3/t8-,15+,16+,18-,20+,21+,23-,24-,25+,26+,27+,30+,31+,32-,33-/m0/s1
• InChI Key: AGCJXRMKEHRGIH-YBAQHRTESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₂₂
• Molecular Weight: 788.70 g/mol
• Exact Mass: 788.20112290 g/mol
• Topological Polar Surface Area (TPSA): 365.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -4.51
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5372	53.72%
Caco-2	-	0.9049	90.49%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6684	66.84%
OATP2B1 inhibitior	-	0.7140	71.40%
OATP1B1 inhibitior	+	0.8954	89.54%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6932	69.32%
P-glycoprotein inhibitior	-	0.4419	44.19%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6494	64.94%
CYP2C9 substrate	-	0.6847	68.47%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	-	0.9550	95.50%
CYP2C9 inhibition	-	0.9252	92.52%
CYP2C19 inhibition	-	0.9129	91.29%
CYP2D6 inhibition	-	0.9613	96.13%
CYP1A2 inhibition	-	0.8948	89.48%
CYP2C8 inhibition	+	0.7084	70.84%
CYP inhibitory promiscuity	-	0.6991	69.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6759	67.59%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	+	0.5099	50.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.7424	74.24%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9289	92.89%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.9187	91.87%
Acute Oral Toxicity (c)	III	0.5567	55.67%
Estrogen receptor binding	+	0.7888	78.88%
Androgen receptor binding	+	0.6015	60.15%
Thyroid receptor binding	+	0.5223	52.23%
Glucocorticoid receptor binding	-	0.5710	57.10%
Aromatase binding	+	0.5284	52.84%
PPAR gamma	+	0.7440	74.40%
Honey bee toxicity	-	0.7275	72.75%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.8024	80.24%

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	99.78%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.74%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.46%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.70%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.80%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.36%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	94.05%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.84%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.69%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.57%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.45%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.29%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.47%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.94%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.64%	95.56%
CHEMBL3194	P02766	Transthyretin	82.28%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.82%	96.21%
CHEMBL4208	P20618	Proteasome component C5	80.81%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.50%	86.92%

Plants that contains it

• Crocus chrysanthus

Cross-Links

• PubChem: 101036570
• LOTUS: LTS0024846
• wikiData: Q104911702