[(2R,3S,4R,5R,6S)-6-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-2-[5,8-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: cbdb0c08-4374-4821-8150-02e02dddb1e5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: [(2R,3S,4R,5R,6S)-6-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-2-[5,8-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(C4=C(C(=C3)O)C(=O)C=C(O4)C5=CC=C(C=C5)O)O)COC(=O)C)O)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[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(C4=C(C(=C3)O)C(=O)C=C(O4)C5=CC=C(C=C5)O)O)COC(=O)C)O)O)O)O)O
• InChI: InChI=1S/C31H34O18/c1-11(32)43-9-19-22(37)25(40)27(42)30(47-19)49-29-26(41)23(38)20(10-44-12(2)33)48-31(29)46-18-8-16(36)21-15(35)7-17(45-28(21)24(18)39)13-3-5-14(34)6-4-13/h3-8,19-20,22-23,25-27,29-31,34,36-42H,9-10H2,1-2H3/t19-,20-,22-,23-,25-,26+,27-,29-,30+,31-/m1/s1
• InChI Key: PWOFHOJJMWJGLT-YMRZOMLSSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₄O₁₈
• Molecular Weight: 694.60 g/mol
• Exact Mass: 694.17451423 g/mol
• Topological Polar Surface Area (TPSA): 278.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.28
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4929	49.29%
Caco-2	-	0.9026	90.26%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6747	67.47%
OATP2B1 inhibitior	-	0.5769	57.69%
OATP1B1 inhibitior	+	0.8572	85.72%
OATP1B3 inhibitior	+	0.9501	95.01%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5701	57.01%
P-glycoprotein inhibitior	-	0.4639	46.39%
P-glycoprotein substrate	-	0.6080	60.80%
CYP3A4 substrate	+	0.6618	66.18%
CYP2C9 substrate	+	0.5319	53.19%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.9500	95.00%
CYP2C9 inhibition	-	0.9017	90.17%
CYP2C19 inhibition	-	0.9109	91.09%
CYP2D6 inhibition	-	0.9608	96.08%
CYP1A2 inhibition	-	0.9051	90.51%
CYP2C8 inhibition	+	0.7292	72.92%
CYP inhibitory promiscuity	-	0.8291	82.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7145	71.45%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9131	91.31%
Skin irritation	-	0.8470	84.70%
Skin corrosion	-	0.9531	95.31%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3636	36.36%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.7162	71.62%
skin sensitisation	-	0.9297	92.97%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8691	86.91%
Acute Oral Toxicity (c)	III	0.6128	61.28%
Estrogen receptor binding	+	0.8400	84.00%
Androgen receptor binding	+	0.7097	70.97%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5867	58.67%
Aromatase binding	+	0.5843	58.43%
PPAR gamma	+	0.7513	75.13%
Honey bee toxicity	-	0.7117	71.17%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9622	96.22%

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	99.14%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.15%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.10%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.68%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.32%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.20%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.63%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.63%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.36%	94.45%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.36%	95.64%
CHEMBL3194	P02766	Transthyretin	89.60%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	89.53%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.94%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.05%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.21%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.88%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.29%	97.21%
CHEMBL5255	O00206	Toll-like receptor 4	82.24%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.20%	95.89%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	81.78%	89.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.20%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.86%	97.28%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.80%	96.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.61%	96.21%

Plants that contains it

• Sideritis brevibracteata
• Stachys anisochila
• Stachys chrysantha

Cross-Links

• PubChem: 101012655
• LOTUS: LTS0088476
• wikiData: Q105215924