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

Details

• Internal ID: 2cd70292-2388-4525-9da2-b6cc054fea29
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4S,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(=CCCC(=CC2C1C(=C)C(=O)O2)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1C/C(=C/CC/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/C)/C
• InChI: InChI=1S/C20H26O4/c1-6-14(4)19(21)23-16-10-12(2)8-7-9-13(3)11-17-18(16)15(5)20(22)24-17/h6,8,11,16-18H,5,7,9-10H2,1-4H3/b12-8+,13-11+,14-6-/t16-,17+,18+/m0/s1
• InChI Key: HXMMJGIMTCOROX-ZWYGKDPNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.04
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9896	98.96%
Caco-2	+	0.8507	85.07%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5897	58.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.8041	80.41%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6432	64.32%
P-glycoprotein inhibitior	+	0.6307	63.07%
P-glycoprotein substrate	-	0.8518	85.18%
CYP3A4 substrate	+	0.5988	59.88%
CYP2C9 substrate	-	0.6159	61.59%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.6579	65.79%
CYP2C9 inhibition	-	0.8670	86.70%
CYP2C19 inhibition	-	0.7530	75.30%
CYP2D6 inhibition	-	0.9497	94.97%
CYP1A2 inhibition	+	0.7283	72.83%
CYP2C8 inhibition	-	0.6884	68.84%
CYP inhibitory promiscuity	-	0.9096	90.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6558	65.58%
Eye corrosion	-	0.9461	94.61%
Eye irritation	-	0.8696	86.96%
Skin irritation	-	0.5189	51.89%
Skin corrosion	-	0.9313	93.13%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7915	79.15%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6928	69.28%
skin sensitisation	-	0.7876	78.76%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.7865	78.65%
Acute Oral Toxicity (c)	III	0.4766	47.66%
Estrogen receptor binding	-	0.6706	67.06%
Androgen receptor binding	-	0.5078	50.78%
Thyroid receptor binding	-	0.5178	51.78%
Glucocorticoid receptor binding	+	0.6033	60.33%
Aromatase binding	-	0.6085	60.85%
PPAR gamma	+	0.5346	53.46%
Honey bee toxicity	-	0.6469	64.69%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9948	99.48%

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	97.38%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.92%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.41%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.92%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.57%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.07%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.66%	95.50%
CHEMBL2581	P07339	Cathepsin D	84.38%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	84.36%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.37%	97.25%

Plants that contains it

• Brachylaena nereifolia
• Tanacetum argenteum

Cross-Links

• PubChem: 10042281
• LOTUS: LTS0237713
• wikiData: Q105035076