[(2R,3R,4S,5R,6R)-6-[(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: 64db59b7-3525-4853-ba57-13beafb45f99
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6R)-6-[(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2O)OCC(C3=CC(=C(C=C3)O)O)O)COC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2O)OC[C@@H](C3=CC(=C(C=C3)O)O)O)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C29H36O16/c1-12-22(36)24(38)25(39)29(43-12)45-27-23(37)20(11-41-21(35)7-3-13-2-5-15(30)17(32)8-13)44-28(26(27)40)42-10-19(34)14-4-6-16(31)18(33)9-14/h2-9,12,19-20,22-34,36-40H,10-11H2,1H3/b7-3+/t12-,19-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1
• InChI Key: CFUBHHJNQFDGOC-FJXYVNTESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₆
• Molecular Weight: 640.60 g/mol
• Exact Mass: 640.20033506 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.52
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6472	64.72%
Caco-2	-	0.9090	90.90%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6640	66.40%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.8847	88.47%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7705	77.05%
P-glycoprotein inhibitior	-	0.6084	60.84%
P-glycoprotein substrate	-	0.6034	60.34%
CYP3A4 substrate	+	0.6238	62.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	-	0.9243	92.43%
CYP2C9 inhibition	-	0.9311	93.11%
CYP2C19 inhibition	-	0.9377	93.77%
CYP2D6 inhibition	-	0.9068	90.68%
CYP1A2 inhibition	-	0.9159	91.59%
CYP2C8 inhibition	+	0.5656	56.56%
CYP inhibitory promiscuity	-	0.7924	79.24%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6481	64.81%
Eye corrosion	-	0.9938	99.38%
Eye irritation	-	0.9196	91.96%
Skin irritation	-	0.8353	83.53%
Skin corrosion	-	0.9492	94.92%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4298	42.98%
Micronuclear	+	0.5707	57.07%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8170	81.70%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9744	97.44%
Acute Oral Toxicity (c)	III	0.7830	78.30%
Estrogen receptor binding	+	0.7589	75.89%
Androgen receptor binding	-	0.5650	56.50%
Thyroid receptor binding	+	0.5656	56.56%
Glucocorticoid receptor binding	+	0.5564	55.64%
Aromatase binding	+	0.5282	52.82%
PPAR gamma	+	0.7032	70.32%
Honey bee toxicity	-	0.6989	69.89%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8928	89.28%

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	99.76%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.49%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.78%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.19%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.05%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.72%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	92.71%	94.73%
CHEMBL2581	P07339	Cathepsin D	90.24%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.20%	99.17%
CHEMBL3194	P02766	Transthyretin	88.95%	90.71%
CHEMBL4208	P20618	Proteasome component C5	88.23%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.99%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.38%	90.71%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.65%	83.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.52%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.54%	85.14%

Plants that contains it

• Paulownia tomentosa
• Sesamum indicum

Cross-Links

• PubChem: 44229631
• LOTUS: LTS0144126
• wikiData: Q104956971