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

Details

• Internal ID: 2a205053-a46c-4238-a1bf-7f06f0ae4ee8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,6Z,10Z,11aR)-10-(acetyloxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1=CCCC(=CC2C(CC1)C(=C)C(=O)O2)COC(=O)C
• SMILES (Isomeric): CC(=O)OC/C/1=C\CC/C(=C/[C@@H]2[C@@H](CC1)C(=C)C(=O)O2)/COC(=O)C
• InChI: InChI=1S/C19H24O6/c1-12-17-8-7-15(10-23-13(2)20)5-4-6-16(11-24-14(3)21)9-18(17)25-19(12)22/h5,9,17-18H,1,4,6-8,10-11H2,2-3H3/b15-5-,16-9-/t17-,18+/m0/s1
• InChI Key: LDHBLZLTTZFVDZ-NCIFBZTISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.15728848 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9870	98.70%
Caco-2	+	0.6147	61.47%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7302	73.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.6455	64.55%
P-glycoprotein inhibitior	-	0.4378	43.78%
P-glycoprotein substrate	-	0.8796	87.96%
CYP3A4 substrate	+	0.5778	57.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8884	88.84%
CYP3A4 inhibition	-	0.7981	79.81%
CYP2C9 inhibition	-	0.7920	79.20%
CYP2C19 inhibition	-	0.6607	66.07%
CYP2D6 inhibition	-	0.8332	83.32%
CYP1A2 inhibition	+	0.6403	64.03%
CYP2C8 inhibition	-	0.6292	62.92%
CYP inhibitory promiscuity	-	0.6840	68.40%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6947	69.47%
Eye corrosion	-	0.9217	92.17%
Eye irritation	-	0.7309	73.09%
Skin irritation	-	0.6475	64.75%
Skin corrosion	-	0.9320	93.20%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5093	50.93%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.6390	63.90%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.5460	54.60%
Acute Oral Toxicity (c)	III	0.6381	63.81%
Estrogen receptor binding	+	0.5937	59.37%
Androgen receptor binding	+	0.5394	53.94%
Thyroid receptor binding	-	0.6580	65.80%
Glucocorticoid receptor binding	+	0.7707	77.07%
Aromatase binding	-	0.5921	59.21%
PPAR gamma	-	0.5755	57.55%
Honey bee toxicity	-	0.8242	82.42%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9935	99.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.69%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.07%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.98%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.42%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.11%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.69%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.02%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.68%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.30%	100.00%

Plants that contains it

• Dicoma capensis
• Dicoma tomentosa
• Rhodanthe moschata

Cross-Links

• PubChem: 14262541
• LOTUS: LTS0012128
• wikiData: Q105150213