Argolide

Details

• Internal ID: 16596ef2-f8fd-4a4e-95a6-055d526eba57
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,6E,10R,11aR)-6,10-dimethyl-3-methylidene-4,5,8,10,11,11a-hexahydro-3aH-cyclodeca[b]furan-2,9-dione
• SMILES (Canonical): CC1CC2C(CCC(=CCC1=O)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@@H]1C[C@@H]2[C@@H](CC/C(=C/CC1=O)/C)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,10,12,14H,3-4,6-8H2,1-2H3/b9-5+/t10-,12+,14-/m1/s1
• InChI Key: WBBCIKNHTYTDRA-YYYMEZEWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• CHEMBL2380796
• BDBM50433435
• NSC780898
• NSC-780898

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9959	99.59%
Caco-2	+	0.8799	87.99%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6172	61.72%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.9108	91.08%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8925	89.25%
P-glycoprotein inhibitior	-	0.8553	85.53%
P-glycoprotein substrate	-	0.8904	89.04%
CYP3A4 substrate	+	0.5701	57.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8743	87.43%
CYP3A4 inhibition	-	0.8318	83.18%
CYP2C9 inhibition	-	0.9389	93.89%
CYP2C19 inhibition	-	0.8271	82.71%
CYP2D6 inhibition	-	0.9330	93.30%
CYP1A2 inhibition	+	0.6891	68.91%
CYP2C8 inhibition	-	0.7276	72.76%
CYP inhibitory promiscuity	-	0.9222	92.22%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6358	63.58%
Eye corrosion	-	0.8863	88.63%
Eye irritation	+	0.6576	65.76%
Skin irritation	-	0.5498	54.98%
Skin corrosion	-	0.9130	91.30%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4466	44.66%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.5297	52.97%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6148	61.48%
Acute Oral Toxicity (c)	III	0.6276	62.76%
Estrogen receptor binding	-	0.7578	75.78%
Androgen receptor binding	+	0.6781	67.81%
Thyroid receptor binding	-	0.6283	62.83%
Glucocorticoid receptor binding	-	0.5164	51.64%
Aromatase binding	-	0.8137	81.37%
PPAR gamma	-	0.7731	77.31%
Honey bee toxicity	-	0.8474	84.74%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9927	99.27%

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	92.65%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.07%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.34%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.35%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.29%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.23%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.92%	86.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.48%	96.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.39%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.26%	86.33%

Plants that contains it

• Ajania fruticulosa
• Artemisia lucentica
• Artemisia obtusiloba var. glabra

Cross-Links

• PubChem: 14466572
• LOTUS: LTS0258385
• wikiData: Q104403097