[(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-(1-hydroxyethenoxymethyl)but-2-enoate

Details

• Internal ID: ef84f87f-73b2-4134-a404-09dd05dbbb80
• 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-(1-hydroxyethenoxymethyl)but-2-enoate
• InChI: InChI=1S/C22H28O6/c1-6-17(12-26-16(5)23)22(25)28-19-11-14(3)9-7-8-13(2)10-18-20(19)15(4)21(24)27-18/h6,9-10,18-20,23H,4-5,7-8,11-12H2,1-3H3/b13-10+,14-9+,17-6-/t18-,19+,20+/m1/s1
• InChI Key: BWEDGPMGFLZDML-PDQYEBQESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₆
• Molecular Weight: 388.50 g/mol
• Exact Mass: 388.18858861 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 4.06
• H-Bond Acceptor: 6
• 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	+	0.9874	98.74%
Caco-2	-	0.5848	58.48%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7504	75.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8944	89.44%
OATP1B3 inhibitior	+	0.9098	90.98%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6683	66.83%
P-glycoprotein inhibitior	+	0.5910	59.10%
P-glycoprotein substrate	-	0.7225	72.25%
CYP3A4 substrate	+	0.6187	61.87%
CYP2C9 substrate	-	0.6183	61.83%
CYP2D6 substrate	-	0.9104	91.04%
CYP3A4 inhibition	+	0.6660	66.60%
CYP2C9 inhibition	-	0.7701	77.01%
CYP2C19 inhibition	-	0.8062	80.62%
CYP2D6 inhibition	-	0.9323	93.23%
CYP1A2 inhibition	+	0.5890	58.90%
CYP2C8 inhibition	-	0.5597	55.97%
CYP inhibitory promiscuity	-	0.9163	91.63%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6811	68.11%
Eye corrosion	-	0.9751	97.51%
Eye irritation	-	0.8845	88.45%
Skin irritation	-	0.5946	59.46%
Skin corrosion	-	0.9429	94.29%
Ames mutagenesis	-	0.6537	65.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4791	47.91%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8653	86.53%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.6510	65.10%
Acute Oral Toxicity (c)	III	0.4910	49.10%
Estrogen receptor binding	+	0.5278	52.78%
Androgen receptor binding	+	0.5454	54.54%
Thyroid receptor binding	+	0.5873	58.73%
Glucocorticoid receptor binding	+	0.7757	77.57%
Aromatase binding	+	0.5883	58.83%
PPAR gamma	+	0.5219	52.19%
Honey bee toxicity	-	0.7484	74.84%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9936	99.36%

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	96.90%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.00%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.36%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.04%	94.45%
CHEMBL2581	P07339	Cathepsin D	86.56%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	85.86%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.66%	95.50%
CHEMBL5028	O14672	ADAM10	83.97%	97.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.13%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.90%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.88%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	82.32%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.23%	97.25%

Plants that contains it

• Brachylaena nereifolia

Cross-Links

• PubChem: 163103599
• LOTUS: LTS0015562
• wikiData: Q104947167