[(2R,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-3-acetyloxy-6-(acetyloxymethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxolan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 96b4ee3b-5b23-4f94-a1b0-80b448d6c475
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(2R,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-3-acetyloxy-6-(acetyloxymethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxolan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(C(C(C(O2)COC(=O)C=CC3=CC(=C(C=C3)O)OC)O)OC(=O)C=CC4=CC(=C(C=C4)O)OC)COC(=O)C=CC5=CC(=C(C=C5)O)OC)OC(=O)C)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)COC(=O)/C=C/C3=CC(=C(C=C3)O)OC)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)OC)COC(=O)/C=C/C5=CC(=C(C=C5)O)OC)OC(=O)C)O)O
• InChI: InChI=1S/C46H50O22/c1-24(47)61-21-35-40(55)42(57)43(64-25(2)48)45(65-35)68-46(23-63-38(53)16-10-27-7-13-30(50)33(19-27)59-4)44(66-39(54)17-11-28-8-14-31(51)34(20-28)60-5)41(56)36(67-46)22-62-37(52)15-9-26-6-12-29(49)32(18-26)58-3/h6-20,35-36,40-45,49-51,55-57H,21-23H2,1-5H3/b15-9+,16-10+,17-11+/t35-,36-,40-,41-,42+,43-,44+,45+,46+/m1/s1
• InChI Key: JRGWEHCLTJUJTI-IYVIWEKNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₅₀O₂₂
• Molecular Weight: 954.90 g/mol
• Exact Mass: 954.27937322 g/mol
• Topological Polar Surface Area (TPSA): 308.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 22
• H-Bond Donor: 6
• Rotatable Bonds: 19

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5827	58.27%
Caco-2	-	0.8680	86.80%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8138	81.38%
OATP2B1 inhibitior	-	0.5824	58.24%
OATP1B1 inhibitior	+	0.8410	84.10%
OATP1B3 inhibitior	+	0.9093	90.93%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9566	95.66%
P-glycoprotein inhibitior	+	0.7647	76.47%
P-glycoprotein substrate	-	0.6274	62.74%
CYP3A4 substrate	+	0.6668	66.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8707	87.07%
CYP3A4 inhibition	-	0.8739	87.39%
CYP2C9 inhibition	-	0.7917	79.17%
CYP2C19 inhibition	-	0.7730	77.30%
CYP2D6 inhibition	-	0.9271	92.71%
CYP1A2 inhibition	-	0.8133	81.33%
CYP2C8 inhibition	+	0.7824	78.24%
CYP inhibitory promiscuity	-	0.7862	78.62%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6408	64.08%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9061	90.61%
Skin irritation	-	0.8471	84.71%
Skin corrosion	-	0.9545	95.45%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7509	75.09%
Micronuclear	-	0.5152	51.52%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8260	82.60%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8975	89.75%
Acute Oral Toxicity (c)	III	0.5955	59.55%
Estrogen receptor binding	+	0.8381	83.81%
Androgen receptor binding	+	0.7187	71.87%
Thyroid receptor binding	+	0.6362	63.62%
Glucocorticoid receptor binding	+	0.7085	70.85%
Aromatase binding	+	0.5766	57.66%
PPAR gamma	+	0.7734	77.34%
Honey bee toxicity	-	0.7143	71.43%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9847	98.47%

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	99.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.60%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.98%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.98%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.66%	89.00%
CHEMBL3194	P02766	Transthyretin	92.06%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.80%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.67%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	91.59%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	91.53%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.08%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.52%	95.50%
CHEMBL4208	P20618	Proteasome component C5	88.49%	90.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.57%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.41%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.27%	97.36%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.23%	89.62%
CHEMBL340	P08684	Cytochrome P450 3A4	83.14%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.07%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	80.62%	92.50%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.41%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.10%	96.95%

Plants that contains it

• Smilax glabra

Cross-Links

• PubChem: 11972466
• NPASS: NPC109577