[(1R,2S,5S,6R,9S,10S,11R,13R)-5-hydroxy-9-methyl-10-[(E)-2-methylbut-2-enoyl]oxy-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.02,6.011,13]tetradecan-5-yl]methyl (Z)-2-methylbut-2-enoate

Details

• Internal ID: 2579d137-0daf-4f01-a2e6-0f675913f33a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(1R,2S,5S,6R,9S,10S,11R,13R)-5-hydroxy-9-methyl-10-[(E)-2-methylbut-2-enoyl]oxy-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.02,6.011,13]tetradecan-5-yl]methyl (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OCC1(C2CCC3(C(C2OC1=O)C(=C)C4C(C3OC(=O)C(=CC)C)O4)C)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)OC[C@]1([C@@H]2CC[C@]3([C@H]([C@@H]2OC1=O)C(=C)[C@@H]4[C@H]([C@H]3OC(=O)/C(=C/C)/C)O4)C)O
• InChI: InChI=1S/C25H32O8/c1-7-12(3)21(26)30-11-25(29)15-9-10-24(6)16(18(15)32-23(25)28)14(5)17-19(31-17)20(24)33-22(27)13(4)8-2/h7-8,15-20,29H,5,9-11H2,1-4,6H3/b12-7-,13-8+/t15-,16+,17-,18-,19-,20-,24+,25-/m1/s1
• InChI Key: KUJBZYFVSIIWFZ-ORAOACIHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₈
• Molecular Weight: 460.50 g/mol
• Exact Mass: 460.20971797 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9802	98.02%
Caco-2	-	0.6838	68.38%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7689	76.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8474	84.74%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6168	61.68%
BSEP inhibitior	+	0.7830	78.30%
P-glycoprotein inhibitior	+	0.6834	68.34%
P-glycoprotein substrate	-	0.7954	79.54%
CYP3A4 substrate	+	0.7098	70.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8893	88.93%
CYP3A4 inhibition	+	0.5135	51.35%
CYP2C9 inhibition	-	0.5879	58.79%
CYP2C19 inhibition	-	0.8134	81.34%
CYP2D6 inhibition	-	0.9435	94.35%
CYP1A2 inhibition	-	0.8096	80.96%
CYP2C8 inhibition	-	0.6134	61.34%
CYP inhibitory promiscuity	-	0.9070	90.70%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5555	55.55%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9235	92.35%
Skin irritation	+	0.5575	55.75%
Skin corrosion	-	0.9282	92.82%
Ames mutagenesis	-	0.6229	62.29%
Human Ether-a-go-go-Related Gene inhibition	-	0.6982	69.82%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.6569	65.69%
skin sensitisation	-	0.8775	87.75%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.4035	40.35%
Estrogen receptor binding	+	0.6265	62.65%
Androgen receptor binding	+	0.6699	66.99%
Thyroid receptor binding	+	0.5587	55.87%
Glucocorticoid receptor binding	+	0.7484	74.84%
Aromatase binding	+	0.5369	53.69%
PPAR gamma	+	0.5630	56.30%
Honey bee toxicity	-	0.7549	75.49%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9950	99.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.34%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.01%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.69%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.64%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.18%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.73%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	88.58%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.58%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.36%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.26%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.99%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	84.96%	97.79%
CHEMBL2581	P07339	Cathepsin D	84.23%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.03%	97.09%
CHEMBL1871	P10275	Androgen Receptor	83.45%	96.43%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.10%	97.14%
CHEMBL299	P17252	Protein kinase C alpha	82.65%	98.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.50%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.04%	100.00%
CHEMBL5028	O14672	ADAM10	81.71%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.62%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.48%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.27%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.24%	91.19%

Plants that contains it

• Ferula varia

Cross-Links

• PubChem: 44445506
• LOTUS: LTS0231215
• wikiData: Q105146181