[(8S)-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R,3S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylpentanoate

Details

• Internal ID: bd1f44ef-0071-4c3e-b2ed-fd331a6ed537
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(8S)-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R,3S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylpentanoate
• InChI: InChI=1S/C16H27NO4/c1-4-11(2)16(20,12(3)18)15(19)21-10-13-7-9-17-8-5-6-14(13)17/h7,11-12,14,18,20H,4-6,8-10H2,1-3H3/t11-,12+,14-,16+/m0/s1
• InChI Key: WNDKUMUAOQFAGL-CQJJVWNLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₇NO₄
• Molecular Weight: 297.39 g/mol
• Exact Mass: 297.19400834 g/mol
• Topological Polar Surface Area (TPSA): 70.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 5
• 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	+	0.8807	88.07%
Caco-2	+	0.7603	76.03%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5233	52.33%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	+	0.9420	94.20%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5724	57.24%
P-glycoprotein inhibitior	-	0.9433	94.33%
P-glycoprotein substrate	-	0.6410	64.10%
CYP3A4 substrate	+	0.5249	52.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6606	66.06%
CYP3A4 inhibition	-	0.9048	90.48%
CYP2C9 inhibition	-	0.7882	78.82%
CYP2C19 inhibition	-	0.8326	83.26%
CYP2D6 inhibition	-	0.7510	75.10%
CYP1A2 inhibition	-	0.7534	75.34%
CYP2C8 inhibition	-	0.7676	76.76%
CYP inhibitory promiscuity	-	0.8307	83.07%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Danger	0.4964	49.64%
Eye corrosion	-	0.9796	97.96%
Eye irritation	-	0.9879	98.79%
Skin irritation	-	0.7552	75.52%
Skin corrosion	-	0.9187	91.87%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6999	69.99%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.9157	91.57%
skin sensitisation	-	0.7882	78.82%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.5880	58.80%
Acute Oral Toxicity (c)	III	0.5878	58.78%
Estrogen receptor binding	+	0.6400	64.00%
Androgen receptor binding	-	0.5680	56.80%
Thyroid receptor binding	-	0.5551	55.51%
Glucocorticoid receptor binding	+	0.6717	67.17%
Aromatase binding	-	0.5793	57.93%
PPAR gamma	-	0.5775	57.75%
Honey bee toxicity	-	0.9478	94.78%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8446	84.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.53%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.49%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.91%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.99%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.86%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.81%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.64%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.78%	95.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.05%	100.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.39%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.81%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.59%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.57%	90.71%

Plants that contains it

• Heliotropium curassavicum

Cross-Links

• PubChem: 162968088
• LOTUS: LTS0011700
• wikiData: Q105309011