[(2R,3S,4R,5R,6S)-3-acetyloxy-6-[(2S,3R,4R,5S,6S)-3-acetyloxy-2-[2-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-hydroxyphenoxy]-5-hydroxy-6-methyloxan-4-yl]oxy-4,5-dihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 31b59771-9d32-401b-92de-99b4624ba348
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: [(2R,3S,4R,5R,6S)-3-acetyloxy-6-[(2S,3R,4R,5S,6S)-3-acetyloxy-2-[2-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-hydroxyphenoxy]-5-hydroxy-6-methyloxan-4-yl]oxy-4,5-dihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(C=C(C=C2)O)C3CC(=O)C4=C(C=C(C=C4O3)O)O)OC(=O)C)OC5C(C(C(C(O5)COC(=O)C)OC(=O)C)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C=C(C=C2)O)[C@@H]3CC(=O)C4=C(C=C(C=C4O3)O)O)OC(=O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C)OC(=O)C)O)O)O
• InChI: InChI=1S/C33H38O18/c1-12-26(41)30(51-32-28(43)27(42)29(46-14(3)35)24(50-32)11-44-13(2)34)31(47-15(4)36)33(45-12)49-21-6-5-16(37)7-18(21)22-10-20(40)25-19(39)8-17(38)9-23(25)48-22/h5-9,12,22,24,26-33,37-39,41-43H,10-11H2,1-4H3/t12-,22-,24+,26-,27+,28+,29+,30+,31+,32-,33-/m0/s1
• InChI Key: RCTZLAGQSNDQPU-JZGAJSQJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₈O₁₈
• Molecular Weight: 722.60 g/mol
• Exact Mass: 722.20581436 g/mol
• Topological Polar Surface Area (TPSA): 264.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.25
• H-Bond Acceptor: 18
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5483	54.83%
Caco-2	-	0.8828	88.28%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7011	70.11%
OATP2B1 inhibitior	-	0.5726	57.26%
OATP1B1 inhibitior	+	0.8803	88.03%
OATP1B3 inhibitior	+	0.8250	82.50%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7720	77.20%
P-glycoprotein inhibitior	+	0.6785	67.85%
P-glycoprotein substrate	+	0.5559	55.59%
CYP3A4 substrate	+	0.6900	69.00%
CYP2C9 substrate	-	0.8251	82.51%
CYP2D6 substrate	-	0.8645	86.45%
CYP3A4 inhibition	-	0.9401	94.01%
CYP2C9 inhibition	-	0.9298	92.98%
CYP2C19 inhibition	-	0.9583	95.83%
CYP2D6 inhibition	-	0.9433	94.33%
CYP1A2 inhibition	-	0.9085	90.85%
CYP2C8 inhibition	+	0.6733	67.33%
CYP inhibitory promiscuity	-	0.7788	77.88%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7248	72.48%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9081	90.81%
Skin irritation	-	0.8395	83.95%
Skin corrosion	-	0.9570	95.70%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5776	57.76%
Micronuclear	+	0.5892	58.92%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9320	93.20%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7180	71.80%
Acute Oral Toxicity (c)	III	0.6642	66.42%
Estrogen receptor binding	+	0.8278	82.78%
Androgen receptor binding	+	0.5459	54.59%
Thyroid receptor binding	+	0.5420	54.20%
Glucocorticoid receptor binding	+	0.7382	73.82%
Aromatase binding	+	0.5588	55.88%
PPAR gamma	+	0.7153	71.53%
Honey bee toxicity	-	0.6921	69.21%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5650	56.50%
Fish aquatic toxicity	+	0.9660	96.60%

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	99.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.08%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.56%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.58%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.38%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.79%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.43%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.34%	99.17%
CHEMBL4208	P20618	Proteasome component C5	91.01%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.31%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.04%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.75%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	86.31%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	85.45%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.34%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.21%	99.23%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.08%	95.78%
CHEMBL340	P08684	Cytochrome P450 3A4	83.81%	91.19%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.24%	99.15%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.18%	85.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.95%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.01%	100.00%

Plants that contains it

• Thelypteris acuminata

Cross-Links

• PubChem: 11995178
• LOTUS: LTS0254655
• wikiData: Q105233968