[(3R,5S,8S,11S,12S,13S,15R,16S)-5-(acetyloxymethyl)-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.13,15.05,15.08,13]heptadec-1-en-16-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 177b101a-ae04-47fc-859b-93ba59feeca2
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: [(3R,5S,8S,11S,12S,13S,15R,16S)-5-(acetyloxymethyl)-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.13,15.05,15.08,13]heptadec-1-en-16-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(C3CC4(C2(O3)CC5(C1(C(CCC5OC4=O)C)C)O)COC(=O)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C2=C([C@H]3C[C@@]4([C@@]2(O3)C[C@@]5([C@]1([C@H](CC[C@@H]5OC4=O)C)C)O)COC(=O)C)C
• InChI: InChI=1S/C26H34O8/c1-7-13(2)21(28)33-20-19-15(4)17-10-24(12-31-16(5)27)22(29)32-18-9-8-14(3)23(20,6)25(18,30)11-26(19,24)34-17/h7,14,17-18,20,30H,8-12H2,1-6H3/b13-7-/t14-,17+,18-,20+,23-,24+,25+,26+/m0/s1
• InChI Key: QXUBAYPXCVQBAG-GNMAKUBHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₈
• Molecular Weight: 474.50 g/mol
• Exact Mass: 474.22536804 g/mol
• Topological Polar Surface Area (TPSA): 108.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.77
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9889	98.89%
Caco-2	-	0.5781	57.81%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8524	85.24%
OATP2B1 inhibitior	-	0.8623	86.23%
OATP1B1 inhibitior	+	0.8516	85.16%
OATP1B3 inhibitior	+	0.9243	92.43%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5668	56.68%
BSEP inhibitior	+	0.8610	86.10%
P-glycoprotein inhibitior	+	0.7086	70.86%
P-glycoprotein substrate	+	0.5442	54.42%
CYP3A4 substrate	+	0.6939	69.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.6789	67.89%
CYP2C9 inhibition	-	0.6452	64.52%
CYP2C19 inhibition	-	0.8763	87.63%
CYP2D6 inhibition	-	0.9518	95.18%
CYP1A2 inhibition	-	0.8500	85.00%
CYP2C8 inhibition	+	0.5347	53.47%
CYP inhibitory promiscuity	-	0.9061	90.61%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4397	43.97%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9019	90.19%
Skin irritation	+	0.6654	66.54%
Skin corrosion	-	0.9366	93.66%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6775	67.75%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5711	57.11%
skin sensitisation	-	0.9266	92.66%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.7105	71.05%
Acute Oral Toxicity (c)	III	0.4710	47.10%
Estrogen receptor binding	+	0.8622	86.22%
Androgen receptor binding	+	0.7344	73.44%
Thyroid receptor binding	+	0.5440	54.40%
Glucocorticoid receptor binding	+	0.8368	83.68%
Aromatase binding	+	0.7630	76.30%
PPAR gamma	+	0.6743	67.43%
Honey bee toxicity	-	0.7302	73.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9911	99.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.39%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.68%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.99%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.56%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.55%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.73%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.43%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.48%	86.33%
CHEMBL2581	P07339	Cathepsin D	85.41%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.09%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.33%	97.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.24%	89.34%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.71%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.62%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.16%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.22%	95.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.13%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.93%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.20%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.98%	99.23%
CHEMBL1871	P10275	Androgen Receptor	80.62%	96.43%

Plants that contains it

• Ligularia veitchiana

Cross-Links

• PubChem: 162914810
• LOTUS: LTS0272313
• wikiData: Q105229894