(7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl 2-hydroxy-2,3-dimethylbutanoate

Details

• Internal ID: 613de8c9-87ac-46a7-9839-774a023336e0
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: (7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl 2-hydroxy-2,3-dimethylbutanoate
• SMILES (Canonical): CC(C)C(C)(C(=O)OCC1=CCN2C1C(CC2)O)O
• SMILES (Isomeric): CC(C)C(C)(C(=O)OCC1=CCN2C1C(CC2)O)O
• InChI: InChI=1S/C14H23NO4/c1-9(2)14(3,18)13(17)19-8-10-4-6-15-7-5-11(16)12(10)15/h4,9,11-12,16,18H,5-8H2,1-3H3
• InChI Key: TZHAMNIFJHFPNN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₃NO₄
• Molecular Weight: 269.34 g/mol
• Exact Mass: 269.16270821 g/mol
• Topological Polar Surface Area (TPSA): 70.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.31
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• ACon1_001564
• NCGC00180377-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8882	88.82%
Caco-2	+	0.6641	66.41%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6721	67.21%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9250	92.50%
OATP1B3 inhibitior	+	0.9425	94.25%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6363	63.63%
P-glycoprotein inhibitior	-	0.9727	97.27%
P-glycoprotein substrate	-	0.6246	62.46%
CYP3A4 substrate	+	0.5501	55.01%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	+	0.3842	38.42%
CYP3A4 inhibition	-	0.9099	90.99%
CYP2C9 inhibition	-	0.8951	89.51%
CYP2C19 inhibition	-	0.8928	89.28%
CYP2D6 inhibition	-	0.7050	70.50%
CYP1A2 inhibition	-	0.8859	88.59%
CYP2C8 inhibition	-	0.9079	90.79%
CYP inhibitory promiscuity	-	0.9172	91.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.5638	56.38%
Eye corrosion	-	0.9815	98.15%
Eye irritation	-	0.9865	98.65%
Skin irritation	-	0.7493	74.93%
Skin corrosion	-	0.9120	91.20%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6932	69.32%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.8010	80.10%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.4787	47.87%
Acute Oral Toxicity (c)	III	0.5299	52.99%
Estrogen receptor binding	-	0.6611	66.11%
Androgen receptor binding	-	0.6376	63.76%
Thyroid receptor binding	-	0.6659	66.59%
Glucocorticoid receptor binding	+	0.6180	61.80%
Aromatase binding	-	0.6073	60.73%
PPAR gamma	-	0.7292	72.92%
Honey bee toxicity	-	0.9136	91.36%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	-	0.6140	61.40%

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	98.90%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.05%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.58%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.74%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.73%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.36%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.44%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.24%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.16%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.73%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.11%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.98%	100.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.47%	90.24%

Plants that contains it

• Ageratum houstonianum

Cross-Links

• PubChem: 22297469
• LOTUS: LTS0213377
• wikiData: Q105268149