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

Details

• Internal ID: 95e793e0-1a9e-4dba-aa35-ac493215cb42
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(1R,8S)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2,3-dimethylbutanoate
• SMILES (Canonical): CC(C)C(C)(C(=O)OCC1CCN2C1C(=CC2)CO)O
• SMILES (Isomeric): CC(C)[C@@](C)(C(=O)OC[C@@H]1CCN2[C@@H]1C(=CC2)CO)O
• InChI: InChI=1S/C15H25NO4/c1-10(2)15(3,19)14(18)20-9-12-5-7-16-6-4-11(8-17)13(12)16/h4,10,12-13,17,19H,5-9H2,1-3H3/t12-,13+,15-/m0/s1
• InChI Key: SGQBWHHTTFQKAN-GUTXKFCHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₅NO₄
• Molecular Weight: 283.36 g/mol
• Exact Mass: 283.17835828 g/mol
• Topological Polar Surface Area (TPSA): 70.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.56
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7868	78.68%
Caco-2	+	0.5893	58.93%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6385	63.85%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.9224	92.24%
OATP1B3 inhibitior	+	0.9386	93.86%
MATE1 inhibitior	-	0.9409	94.09%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6282	62.82%
P-glycoprotein inhibitior	-	0.9376	93.76%
P-glycoprotein substrate	-	0.5078	50.78%
CYP3A4 substrate	+	0.5249	52.49%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.6598	65.98%
CYP3A4 inhibition	-	0.8615	86.15%
CYP2C9 inhibition	-	0.8177	81.77%
CYP2C19 inhibition	-	0.8139	81.39%
CYP2D6 inhibition	-	0.7563	75.63%
CYP1A2 inhibition	-	0.7857	78.57%
CYP2C8 inhibition	-	0.9137	91.37%
CYP inhibitory promiscuity	-	0.7623	76.23%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.4198	41.98%
Eye corrosion	-	0.9730	97.30%
Eye irritation	-	0.9844	98.44%
Skin irritation	-	0.7420	74.20%
Skin corrosion	-	0.9017	90.17%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8081	80.81%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.7486	74.86%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6794	67.94%
Acute Oral Toxicity (c)	III	0.5832	58.32%
Estrogen receptor binding	-	0.6541	65.41%
Androgen receptor binding	-	0.6399	63.99%
Thyroid receptor binding	-	0.5199	51.99%
Glucocorticoid receptor binding	+	0.6259	62.59%
Aromatase binding	-	0.7030	70.30%
PPAR gamma	-	0.7156	71.56%
Honey bee toxicity	-	0.9298	92.98%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.4374	43.74%

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	99.05%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.85%	97.25%
CHEMBL2581	P07339	Cathepsin D	96.90%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.19%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.63%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.71%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.51%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.90%	85.14%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.72%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.39%	95.56%
CHEMBL5028	O14672	ADAM10	81.97%	97.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.55%	93.04%

Plants that contains it

• Ageratum houstonianum

Cross-Links

• PubChem: 102019615
• LOTUS: LTS0075458
• wikiData: Q105252497