[(3aS,6Z,10Z,11aR)-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate

Details

• Internal ID: 573af071-4210-4d12-a32b-f7f4b4ea69cb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,6Z,10Z,11aR)-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate
• SMILES (Canonical): CC(=C)C(=O)OCC1=CCCC(=CC2C(CC1)C(=C)C(=O)O2)CO
• SMILES (Isomeric): CC(=C)C(=O)OC/C/1=C\CC/C(=C/[C@@H]2[C@@H](CC1)C(=C)C(=O)O2)/CO
• InChI: InChI=1S/C19H24O5/c1-12(2)18(21)23-11-14-5-4-6-15(10-20)9-17-16(8-7-14)13(3)19(22)24-17/h5,9,16-17,20H,1,3-4,6-8,10-11H2,2H3/b14-5-,15-9-/t16-,17+/m0/s1
• InChI Key: NZZTWFCZLOGSOZ-DPEIZSTQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 5
• 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	+	0.9531	95.31%
Caco-2	-	0.5944	59.44%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7991	79.91%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.9042	90.42%
OATP1B3 inhibitior	+	0.9495	94.95%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.6070	60.70%
BSEP inhibitior	-	0.5408	54.08%
P-glycoprotein inhibitior	-	0.7048	70.48%
P-glycoprotein substrate	-	0.7768	77.68%
CYP3A4 substrate	+	0.6188	61.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.7694	76.94%
CYP2C9 inhibition	-	0.7520	75.20%
CYP2C19 inhibition	-	0.7114	71.14%
CYP2D6 inhibition	-	0.8828	88.28%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.4692	46.92%
CYP inhibitory promiscuity	-	0.7881	78.81%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.6476	64.76%
Eye corrosion	-	0.9562	95.62%
Eye irritation	-	0.5370	53.70%
Skin irritation	-	0.6638	66.38%
Skin corrosion	-	0.9289	92.89%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6377	63.77%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7683	76.83%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5747	57.47%
Acute Oral Toxicity (c)	III	0.6229	62.29%
Estrogen receptor binding	-	0.5782	57.82%
Androgen receptor binding	-	0.4874	48.74%
Thyroid receptor binding	-	0.5508	55.08%
Glucocorticoid receptor binding	+	0.8803	88.03%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.5059	50.59%
Honey bee toxicity	-	0.8199	81.99%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9688	96.88%

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	96.44%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.80%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.26%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.42%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.04%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.97%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.19%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.54%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.52%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.15%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	80.20%	97.79%

Plants that contains it

• Dicoma macrocephala

Cross-Links

• PubChem: 162970810
• LOTUS: LTS0063310
• wikiData: Q105188550