(3S,4S,4aR,8R)-4-ethenyl-3-ethoxy-8-methoxy-3,4,4a,5,6,7-hexahydropyrano[3,4-c]pyridin-8-ol

Details

• Internal ID: 6e2eae0c-90fd-44b7-915c-858730bee6f7
• Taxonomy: Organoheterocyclic compounds > Piperidines
• IUPAC Name: (3S,4S,4aR,8R)-4-ethenyl-3-ethoxy-8-methoxy-3,4,4a,5,6,7-hexahydropyrano[3,4-c]pyridin-8-ol
• SMILES (Canonical): CCOC1C(C2CCNC(C2=CO1)(O)OC)C=C
• SMILES (Isomeric): CCO[C@@H]1[C@H]([C@H]2CCN[C@](C2=CO1)(O)OC)C=C
• InChI: InChI=1S/C13H21NO4/c1-4-9-10-6-7-14-13(15,16-3)11(10)8-18-12(9)17-5-2/h4,8-10,12,14-15H,1,5-7H2,2-3H3/t9-,10+,12-,13+/m0/s1
• InChI Key: OIUMMEQZEXIQAL-JULQROHOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₁NO₄
• Molecular Weight: 255.31 g/mol
• Exact Mass: 255.14705815 g/mol
• Topological Polar Surface Area (TPSA): 60.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.97
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8796	87.96%
Caco-2	+	0.5091	50.91%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4436	44.36%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.8928	89.28%
OATP1B3 inhibitior	+	0.9405	94.05%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8976	89.76%
P-glycoprotein inhibitior	-	0.9075	90.75%
P-glycoprotein substrate	-	0.7333	73.33%
CYP3A4 substrate	+	0.5769	57.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7859	78.59%
CYP3A4 inhibition	-	0.7311	73.11%
CYP2C9 inhibition	-	0.7419	74.19%
CYP2C19 inhibition	-	0.7221	72.21%
CYP2D6 inhibition	-	0.8393	83.93%
CYP1A2 inhibition	-	0.6676	66.76%
CYP2C8 inhibition	+	0.4730	47.30%
CYP inhibitory promiscuity	-	0.7430	74.30%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5301	53.01%
Eye corrosion	-	0.9804	98.04%
Eye irritation	-	0.9876	98.76%
Skin irritation	-	0.7561	75.61%
Skin corrosion	-	0.9199	91.99%
Ames mutagenesis	-	0.6240	62.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.5214	52.14%
Micronuclear	+	0.7068	70.68%
Hepatotoxicity	+	0.5659	56.59%
skin sensitisation	-	0.8258	82.58%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5206	52.06%
Acute Oral Toxicity (c)	III	0.5699	56.99%
Estrogen receptor binding	+	0.5649	56.49%
Androgen receptor binding	+	0.5335	53.35%
Thyroid receptor binding	+	0.7305	73.05%
Glucocorticoid receptor binding	+	0.5511	55.11%
Aromatase binding	-	0.5488	54.88%
PPAR gamma	-	0.5980	59.80%
Honey bee toxicity	-	0.8815	88.15%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.4200	42.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.05%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.36%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.26%	97.25%
CHEMBL240	Q12809	HERG	95.89%	89.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.72%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.98%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.19%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	84.15%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.15%	95.56%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.20%	92.88%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.28%	92.94%

Plants that contains it

• Schenkia spicata

Cross-Links

• PubChem: 163043681
• LOTUS: LTS0190877
• wikiData: Q105192766