Fasicularin

Details

• Internal ID: 5bc07f66-1343-479a-8f3c-876cdc6279a4
• IUPAC Name: [(3S,6R,8aR,12aR)-6-hexyl-1,2,3,4,6,7,8,8a,9,10,11,12-dodecahydrobenzo[j]quinolizin-3-yl] thiocyanate
• SMILES (Canonical): CCCCCCC1CCC2CCCCC23N1CC(CC3)SC#N
• SMILES (Isomeric): CCCCCC[C@@H]1CC[C@H]2CCCC[C@]23N1C[C@H](CC3)SC#N
• InChI: InChI=1S/C20H34N2S/c1-2-3-4-5-9-18-11-10-17-8-6-7-13-20(17)14-12-19(23-16-21)15-22(18)20/h17-19H,2-15H2,1H3/t17-,18-,19+,20-/m1/s1
• InChI Key: VMURKEGWZZKIHB-YSTOQKLRSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄N₂S
• Molecular Weight: 334.60 g/mol
• Exact Mass: 334.24427027 g/mol
• Topological Polar Surface Area (TPSA): 52.30 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 5.73
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• [(3S,6R,8aR,12aR)-6-hexyl-1,2,3,4,6,7,8,8a,9,10,11,12-dodecahydrobenzo[j]quinolizin-3-yl] thiocyanate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9767	97.67%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Lysosomes	0.5572	55.72%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8936	89.36%
OATP1B3 inhibitior	+	0.9470	94.70%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.8268	82.68%
P-glycoprotein inhibitior	-	0.8831	88.31%
P-glycoprotein substrate	-	0.5114	51.14%
CYP3A4 substrate	+	0.6220	62.20%
CYP2C9 substrate	-	0.8081	80.81%
CYP2D6 substrate	+	0.5442	54.42%
CYP3A4 inhibition	-	0.7097	70.97%
CYP2C9 inhibition	-	0.6085	60.85%
CYP2C19 inhibition	+	0.6645	66.45%
CYP2D6 inhibition	-	0.7380	73.80%
CYP1A2 inhibition	-	0.5121	51.21%
CYP2C8 inhibition	-	0.6279	62.79%
CYP inhibitory promiscuity	+	0.6899	68.99%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6862	68.62%
Eye corrosion	-	0.9370	93.70%
Eye irritation	-	0.8976	89.76%
Skin irritation	-	0.6942	69.42%
Skin corrosion	-	0.7505	75.05%
Ames mutagenesis	-	0.9037	90.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5423	54.23%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5647	56.47%
skin sensitisation	-	0.7999	79.99%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5290	52.90%
Acute Oral Toxicity (c)	III	0.7451	74.51%
Estrogen receptor binding	+	0.6719	67.19%
Androgen receptor binding	-	0.5554	55.54%
Thyroid receptor binding	+	0.5750	57.50%
Glucocorticoid receptor binding	+	0.5824	58.24%
Aromatase binding	-	0.5742	57.42%
PPAR gamma	-	0.6495	64.95%
Honey bee toxicity	-	0.8812	88.12%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.8168	81.68%
Fish aquatic toxicity	+	0.9406	94.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL230	P35354	Cyclooxygenase-2	99.70%	89.63%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.76%	95.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	97.86%	96.38%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	97.28%	91.81%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.13%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.74%	92.86%
CHEMBL2581	P07339	Cathepsin D	96.25%	98.95%
CHEMBL4072	P07858	Cathepsin B	95.88%	93.67%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.25%	97.25%
CHEMBL1978	P11511	Cytochrome P450 19A1	94.12%	91.76%
CHEMBL259	P32245	Melanocortin receptor 4	93.77%	95.38%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	92.95%	90.24%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	92.68%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	92.43%	95.50%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	90.90%	98.33%
CHEMBL1871	P10275	Androgen Receptor	90.75%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.70%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.37%	90.17%
CHEMBL238	Q01959	Dopamine transporter	90.02%	95.88%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.77%	93.56%
CHEMBL3837	P07711	Cathepsin L	89.72%	96.61%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	88.75%	95.34%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	88.29%	92.08%
CHEMBL237	P41145	Kappa opioid receptor	87.97%	98.10%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	87.96%	95.58%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.54%	93.99%
CHEMBL204	P00734	Thrombin	86.49%	96.01%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	86.47%	96.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	86.41%	97.50%
CHEMBL4660	P28907	Lymphocyte differentiation antigen CD38	85.65%	95.27%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.51%	82.69%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	85.42%	96.25%
CHEMBL226	P30542	Adenosine A1 receptor	84.59%	95.93%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.35%	100.00%
CHEMBL1914	P06276	Butyrylcholinesterase	84.22%	95.00%
CHEMBL4105838	Q96GG9	DCN1-like protein 1	84.09%	95.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.17%	92.50%
CHEMBL4198	P98170	Inhibitor of apoptosis protein 3	83.04%	97.79%
CHEMBL4608	P33032	Melanocortin receptor 5	82.81%	97.00%
CHEMBL1968	P07099	Epoxide hydrolase 1	82.45%	98.57%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.38%	94.08%
CHEMBL4644	P41968	Melanocortin receptor 3	82.14%	99.52%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	81.58%	97.64%
CHEMBL268	P43235	Cathepsin K	81.38%	96.85%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.10%	90.24%
CHEMBL2094135	Q96BI3	Gamma-secretase	80.18%	98.05%
CHEMBL3012	Q13946	Phosphodiesterase 7A	80.11%	99.29%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10854221
• LOTUS: LTS0202194
• wikiData: Q105289310