Ketopelenolide D

Details

• Internal ID: 91f669f6-3113-41d4-8eef-209e470ac43d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (1S,4R,6R,9S,11R,14S)-4,9,14-trimethyl-5,12-dioxatricyclo[9.3.0.04,6]tetradecane-8,13-dione
• SMILES (Canonical): CC1CC2C(CCC3(C(O3)CC1=O)C)C(C(=O)O2)C
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@@H](CC[C@@]3([C@H](O3)CC1=O)C)[C@@H](C(=O)O2)C
• InChI: InChI=1S/C15H22O4/c1-8-6-12-10(9(2)14(17)18-12)4-5-15(3)13(19-15)7-11(8)16/h8-10,12-13H,4-7H2,1-3H3/t8-,9-,10-,12+,13+,15+/m0/s1
• InChI Key: WGXCGTITYIOZAU-FBURBDLBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 55.90 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.10
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• (1S,4R,6R,9S,11R,14S)-4,9,14-Trimethyl-5,12-dioxatricyclo[9.3.0.04,6]tetradecane-8,13-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9737	97.37%
Caco-2	+	0.7932	79.32%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6129	61.29%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.9183	91.83%
OATP1B3 inhibitior	+	0.9729	97.29%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7869	78.69%
P-glycoprotein inhibitior	-	0.7797	77.97%
P-glycoprotein substrate	-	0.7283	72.83%
CYP3A4 substrate	+	0.5964	59.64%
CYP2C9 substrate	-	0.5954	59.54%
CYP2D6 substrate	-	0.8417	84.17%
CYP3A4 inhibition	-	0.8525	85.25%
CYP2C9 inhibition	-	0.8742	87.42%
CYP2C19 inhibition	-	0.8998	89.98%
CYP2D6 inhibition	-	0.9594	95.94%
CYP1A2 inhibition	-	0.5997	59.97%
CYP2C8 inhibition	-	0.8533	85.33%
CYP inhibitory promiscuity	-	0.9895	98.95%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6431	64.31%
Eye corrosion	-	0.9645	96.45%
Eye irritation	-	0.8703	87.03%
Skin irritation	-	0.5408	54.08%
Skin corrosion	-	0.6293	62.93%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6322	63.22%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8161	81.61%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7648	76.48%
Acute Oral Toxicity (c)	III	0.5847	58.47%
Estrogen receptor binding	+	0.7062	70.62%
Androgen receptor binding	+	0.6944	69.44%
Thyroid receptor binding	+	0.5145	51.45%
Glucocorticoid receptor binding	+	0.6179	61.79%
Aromatase binding	-	0.6702	67.02%
PPAR gamma	-	0.6186	61.86%
Honey bee toxicity	-	0.7861	78.61%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9435	94.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.88%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.20%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.32%	97.09%
CHEMBL1902	P62942	FK506-binding protein 1A	88.30%	97.05%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.22%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.51%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.27%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.10%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.61%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.96%	96.77%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.73%	93.04%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.47%	86.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.98%	86.33%

Plants that contains it

• Artemisia arborescens

Cross-Links

• PubChem: 25178792
• LOTUS: LTS0180077
• wikiData: Q105305025