[(8S)-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl (2R)-2,3-dihydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate

Details

• Internal ID: b4e0d1d5-b20a-4087-a059-9fd0c58e59c2
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(8S)-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl (2R)-2,3-dihydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
• SMILES (Canonical): CC(C(C(=O)OCC1=CC[N+]2(C1CCC2)[O-])(C(C)(C)O)O)OC
• SMILES (Isomeric): C[C@H]([C@](C(=O)OCC1=CC[N+]2([C@H]1CCC2)[O-])(C(C)(C)O)O)OC
• InChI: InChI=1S/C16H27NO6/c1-11(22-4)16(20,15(2,3)19)14(18)23-10-12-7-9-17(21)8-5-6-13(12)17/h7,11,13,19-20H,5-6,8-10H2,1-4H3/t11-,13+,16+,17?/m1/s1
• InChI Key: HBLMREVMAXBIKQ-DYLCFMGLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₇NO₆
• Molecular Weight: 329.39 g/mol
• Exact Mass: 329.18383758 g/mol
• Topological Polar Surface Area (TPSA): 94.10 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): 0.48
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8529	85.29%
Caco-2	-	0.5363	53.63%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5445	54.45%
OATP2B1 inhibitior	-	0.8517	85.17%
OATP1B1 inhibitior	+	0.8907	89.07%
OATP1B3 inhibitior	+	0.9373	93.73%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7181	71.81%
P-glycoprotein inhibitior	-	0.9052	90.52%
P-glycoprotein substrate	-	0.6231	62.31%
CYP3A4 substrate	+	0.5808	58.08%
CYP2C9 substrate	-	0.7942	79.42%
CYP2D6 substrate	-	0.8505	85.05%
CYP3A4 inhibition	-	0.9645	96.45%
CYP2C9 inhibition	-	0.8334	83.34%
CYP2C19 inhibition	-	0.7789	77.89%
CYP2D6 inhibition	-	0.8316	83.16%
CYP1A2 inhibition	-	0.8255	82.55%
CYP2C8 inhibition	+	0.4919	49.19%
CYP inhibitory promiscuity	-	0.9692	96.92%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Danger	0.5844	58.44%
Eye corrosion	-	0.9760	97.60%
Eye irritation	-	0.9344	93.44%
Skin irritation	-	0.7592	75.92%
Skin corrosion	-	0.9167	91.67%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6343	63.43%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8214	82.14%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7525	75.25%
Acute Oral Toxicity (c)	III	0.4859	48.59%
Estrogen receptor binding	+	0.7819	78.19%
Androgen receptor binding	+	0.6380	63.80%
Thyroid receptor binding	+	0.5559	55.59%
Glucocorticoid receptor binding	+	0.8279	82.79%
Aromatase binding	+	0.7062	70.62%
PPAR gamma	-	0.5172	51.72%
Honey bee toxicity	-	0.8663	86.63%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.4639	46.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.69%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.98%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.25%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.67%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.02%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.19%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.58%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.06%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.86%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.23%	92.62%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101044825
• LOTUS: LTS0076768
• wikiData: Q105025364