(3aS,4R,5R,6E,10E,11aR)-4,5-dihydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: 854b6e1d-2c29-494a-9028-87a777d0e04d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,4R,5R,6E,10E,11aR)-4,5-dihydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CC2C(C(C(C(=CCC1)C)O)O)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\[C@@H]2[C@H]([C@H]([C@@H](/C(=C/CC1)/C)O)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O4/c1-8-5-4-6-9(2)13(16)14(17)12-10(3)15(18)19-11(12)7-8/h6-7,11-14,16-17H,3-5H2,1-2H3/b8-7+,9-6+/t11-,12-,13-,14-/m1/s1
• InChI Key: NNLKMZXSOLUXBB-WBSDRIRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9338	93.38%
Caco-2	+	0.6451	64.51%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5011	50.11%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.9242	92.42%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9383	93.83%
P-glycoprotein inhibitior	-	0.8975	89.75%
P-glycoprotein substrate	-	0.9012	90.12%
CYP3A4 substrate	+	0.5313	53.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8344	83.44%
CYP3A4 inhibition	-	0.8208	82.08%
CYP2C9 inhibition	-	0.7995	79.95%
CYP2C19 inhibition	-	0.7400	74.00%
CYP2D6 inhibition	-	0.8797	87.97%
CYP1A2 inhibition	+	0.7098	70.98%
CYP2C8 inhibition	-	0.8644	86.44%
CYP inhibitory promiscuity	-	0.8564	85.64%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5336	53.36%
Eye corrosion	-	0.9644	96.44%
Eye irritation	-	0.9296	92.96%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8415	84.15%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8166	81.66%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.7331	73.31%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5743	57.43%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6543	65.43%
Acute Oral Toxicity (c)	III	0.3653	36.53%
Estrogen receptor binding	-	0.5656	56.56%
Androgen receptor binding	-	0.6690	66.90%
Thyroid receptor binding	-	0.6489	64.89%
Glucocorticoid receptor binding	+	0.6079	60.79%
Aromatase binding	-	0.7211	72.11%
PPAR gamma	-	0.5503	55.03%
Honey bee toxicity	-	0.8339	83.39%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9695	96.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.22%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.88%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.15%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.43%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	84.86%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.09%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.72%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.98%	100.00%

Plants that contains it

• Tanacetum vulgare

Cross-Links

• PubChem: 162969527
• LOTUS: LTS0142141
• wikiData: Q105182200