Lettowienolide

Details

• Internal ID: 601304d5-f9e9-49bc-a98b-e4a4ae5d58c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 7-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-hydroxy-3H-1-benzofuran-2-one
• SMILES (Canonical): CC(=CCCC(=CCC1=CC(=CC2=C1OC(=O)C2)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=CC(=CC2=C1OC(=O)C2)O)/C)C
• InChI: InChI=1S/C18H22O3/c1-12(2)5-4-6-13(3)7-8-14-9-16(19)10-15-11-17(20)21-18(14)15/h5,7,9-10,19H,4,6,8,11H2,1-3H3/b13-7+
• InChI Key: BQSTWVNVLQVIEE-NTUHNPAUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₃
• Molecular Weight: 286.40 g/mol
• Exact Mass: 286.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.09
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• Denudalide
• 1189105-39-2
• HY-N10928
• CS-0637583

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	+	0.7258	72.58%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6893	68.93%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.8785	87.85%
OATP1B3 inhibitior	+	0.9289	92.89%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.6175	61.75%
P-glycoprotein inhibitior	-	0.8161	81.61%
P-glycoprotein substrate	-	0.9068	90.68%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.7855	78.55%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.6370	63.70%
CYP2C19 inhibition	+	0.6202	62.02%
CYP2D6 inhibition	-	0.8127	81.27%
CYP1A2 inhibition	+	0.8006	80.06%
CYP2C8 inhibition	-	0.7977	79.77%
CYP inhibitory promiscuity	+	0.5450	54.50%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6424	64.24%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.5732	57.32%
Skin irritation	-	0.6913	69.13%
Skin corrosion	-	0.9377	93.77%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6752	67.52%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.5733	57.33%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5623	56.23%
Acute Oral Toxicity (c)	III	0.5171	51.71%
Estrogen receptor binding	+	0.7927	79.27%
Androgen receptor binding	-	0.5311	53.11%
Thyroid receptor binding	+	0.5878	58.78%
Glucocorticoid receptor binding	+	0.6683	66.83%
Aromatase binding	-	0.5177	51.77%
PPAR gamma	+	0.8927	89.27%
Honey bee toxicity	-	0.8871	88.71%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9964	99.64%

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	99.08%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	95.43%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.52%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.90%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.72%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.14%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.70%	95.56%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	87.27%	93.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.65%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.67%	90.71%

Plants that contains it

• Lettowianthus stellatus
• Magnolia denudata

Cross-Links

• PubChem: 102025309
• NPASS: NPC58455
• LOTUS: LTS0172481
• wikiData: Q104944554