(9-Acetyloxy-5-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl) 2-methylbut-2-enoate

Details

• Internal ID: 14d1637b-1629-4c5b-876a-b4d7a704fc85
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (9-acetyloxy-5-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl) 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(C=C(C(CC=C(C1O)C)OC(=O)C)C)OC(=O)C2=C
• SMILES (Isomeric): CC=C(C)C(=O)OC1C2C(C=C(C(CC=C(C1O)C)OC(=O)C)C)OC(=O)C2=C
• InChI: InChI=1S/C22H28O7/c1-7-11(2)21(25)29-20-18-14(5)22(26)28-17(18)10-13(4)16(27-15(6)23)9-8-12(3)19(20)24/h7-8,10,16-20,24H,5,9H2,1-4,6H3
• InChI Key: JWMHJIFDEKQJQY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.18350323 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9694	96.94%
Caco-2	+	0.5646	56.46%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5901	59.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8549	85.49%
OATP1B3 inhibitior	+	0.8885	88.85%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8154	81.54%
P-glycoprotein inhibitior	+	0.7407	74.07%
P-glycoprotein substrate	-	0.7402	74.02%
CYP3A4 substrate	+	0.6083	60.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9014	90.14%
CYP3A4 inhibition	-	0.7494	74.94%
CYP2C9 inhibition	-	0.8890	88.90%
CYP2C19 inhibition	-	0.8067	80.67%
CYP2D6 inhibition	-	0.9490	94.90%
CYP1A2 inhibition	-	0.6111	61.11%
CYP2C8 inhibition	-	0.7449	74.49%
CYP inhibitory promiscuity	-	0.8900	89.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5160	51.60%
Eye corrosion	-	0.9545	95.45%
Eye irritation	-	0.9028	90.28%
Skin irritation	-	0.5989	59.89%
Skin corrosion	-	0.9171	91.71%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4225	42.25%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.7456	74.56%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6091	60.91%
Acute Oral Toxicity (c)	II	0.3415	34.15%
Estrogen receptor binding	+	0.6710	67.10%
Androgen receptor binding	-	0.5898	58.98%
Thyroid receptor binding	-	0.5126	51.26%
Glucocorticoid receptor binding	+	0.7370	73.70%
Aromatase binding	-	0.6722	67.22%
PPAR gamma	+	0.5969	59.69%
Honey bee toxicity	-	0.6441	64.41%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9432	94.32%

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	94.52%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.06%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.06%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.96%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.58%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.50%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.91%	99.23%
CHEMBL2581	P07339	Cathepsin D	84.90%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.91%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.10%	95.50%

Plants that contains it

• Lasiolaena morii
• Lasiolaena santosii
• Montanoa revealii
• Stylotrichium rotundifolium

Cross-Links

• PubChem: 3795216
• LOTUS: LTS0208803
• wikiData: Q105136219