[(2S,3R,4R,5R,6S)-4,5-dihydroxy-2-[[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: e89d5f9e-1cfc-4272-a366-ef1d6135b3e0
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3R,4R,5R,6S)-4,5-dihydroxy-2-[[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)OC(=O)C=CC6=CC(=C(C=C6)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]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC(=O)/C=C/C6=CC(=C(C=C6)O)O)O)O
• InChI: InChI=1S/C30H38O17/c1-11-19(36)22(39)25(44-17(35)5-3-12-2-4-14(33)15(34)8-12)29(42-11)45-24-13-6-7-41-27(18(13)30(10-32)26(24)47-30)46-28-23(40)21(38)20(37)16(9-31)43-28/h2-8,11,13,16,18-29,31-34,36-40H,9-10H2,1H3/b5-3+/t11-,13+,16+,18+,19-,20+,21-,22+,23+,24-,25+,26-,27-,28-,29-,30+/m0/s1
• InChI Key: DZJHQAIWIGSEOY-LAJFDIHTSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₇
• Molecular Weight: 670.60 g/mol
• Exact Mass: 670.21089974 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -3.06
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

• ACon1_000438
• NCGC00169079-01
• NCGC00169079-02
• BRD-K57158161-001-01-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6506	65.06%
Caco-2	-	0.8953	89.53%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6394	63.94%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8338	83.38%
OATP1B3 inhibitior	+	0.9620	96.20%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7005	70.05%
P-glycoprotein inhibitior	-	0.4832	48.32%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6911	69.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8727	87.27%
CYP3A4 inhibition	-	0.9263	92.63%
CYP2C9 inhibition	-	0.8672	86.72%
CYP2C19 inhibition	-	0.7360	73.60%
CYP2D6 inhibition	-	0.8925	89.25%
CYP1A2 inhibition	-	0.8376	83.76%
CYP2C8 inhibition	+	0.6874	68.74%
CYP inhibitory promiscuity	-	0.6825	68.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5683	56.83%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9168	91.68%
Skin irritation	-	0.7787	77.87%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4712	47.12%
Micronuclear	+	0.5333	53.33%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.7776	77.76%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.9075	90.75%
Acute Oral Toxicity (c)	III	0.5086	50.86%
Estrogen receptor binding	+	0.7245	72.45%
Androgen receptor binding	+	0.5211	52.11%
Thyroid receptor binding	+	0.5239	52.39%
Glucocorticoid receptor binding	+	0.6232	62.32%
Aromatase binding	-	0.4876	48.76%
PPAR gamma	+	0.6879	68.79%
Honey bee toxicity	-	0.6907	69.07%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8099	80.99%

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	99.87%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.58%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.84%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.08%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.97%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.11%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.03%	96.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	91.75%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	91.31%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.14%	97.36%
CHEMBL4208	P20618	Proteasome component C5	88.86%	90.00%
CHEMBL3194	P02766	Transthyretin	88.03%	90.71%
CHEMBL2581	P07339	Cathepsin D	87.05%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.95%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.06%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.97%	86.92%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.55%	92.94%

Plants that contains it

• Juniperus chinensis
• Premna odorata
• Verbascum thapsus

Cross-Links

• PubChem: 14263156
• LOTUS: LTS0217063
• wikiData: Q104962186