Simsiolide

Details

• Internal ID: 1bde971f-72e8-43f8-9704-eeb6e8de513f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (1S,2S,3R,5R,8Z,11R)-2-hydroxy-5,9-dimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.03,5]tetradec-8-en-13-one
• SMILES (Canonical): CC1=CCCC2(C(O2)C(C3C(C1)OC(=O)C3=C)O)C
• SMILES (Isomeric): C/C/1=C/CC[C@@]2([C@H](O2)[C@H]([C@H]3[C@@H](C1)OC(=O)C3=C)O)C
• InChI: InChI=1S/C15H20O4/c1-8-5-4-6-15(3)13(19-15)12(16)11-9(2)14(17)18-10(11)7-8/h5,10-13,16H,2,4,6-7H2,1,3H3/b8-5-/t10-,11-,12+,13-,15-/m1/s1
• InChI Key: ZMFCIMWRPFSUCY-OKSPISFVSA-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): 59.10 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.73
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9682	96.82%
Caco-2	+	0.7816	78.16%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6504	65.04%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9364	93.64%
OATP1B3 inhibitior	+	0.9299	92.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.9388	93.88%
P-glycoprotein inhibitior	-	0.8895	88.95%
P-glycoprotein substrate	-	0.8459	84.59%
CYP3A4 substrate	+	0.5879	58.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8367	83.67%
CYP3A4 inhibition	-	0.8186	81.86%
CYP2C9 inhibition	-	0.8872	88.72%
CYP2C19 inhibition	-	0.8995	89.95%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	+	0.8140	81.40%
CYP2C8 inhibition	-	0.7654	76.54%
CYP inhibitory promiscuity	-	0.9558	95.58%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4953	49.53%
Eye corrosion	-	0.9808	98.08%
Eye irritation	-	0.7498	74.98%
Skin irritation	+	0.5240	52.40%
Skin corrosion	-	0.8760	87.60%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6511	65.11%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5836	58.36%
skin sensitisation	-	0.7558	75.58%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.9039	90.39%
Acute Oral Toxicity (c)	III	0.4610	46.10%
Estrogen receptor binding	+	0.5364	53.64%
Androgen receptor binding	+	0.5687	56.87%
Thyroid receptor binding	+	0.5643	56.43%
Glucocorticoid receptor binding	+	0.6873	68.73%
Aromatase binding	-	0.6449	64.49%
PPAR gamma	+	0.6764	67.64%
Honey bee toxicity	-	0.7582	75.82%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9802	98.02%

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	94.06%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	93.05%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.61%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.74%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.46%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.21%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.40%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.12%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.03%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.30%	93.03%
CHEMBL3401	O75469	Pregnane X receptor	82.79%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.26%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.39%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.20%	94.00%

Plants that contains it

• Helianthus argophyllus

Cross-Links

• PubChem: 101967113
• LOTUS: LTS0272249
• wikiData: Q105379425