[(1R,8R)-7-[[(Z)-3-hydroxyprop-2-enoyl]oxymethyl]-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: 10d6523a-129c-4bc9-8cd2-158890c6e250
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(1R,8R)-7-[[(Z)-3-hydroxyprop-2-enoyl]oxymethyl]-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl] (E)-2-methylbut-2-enoate
• InChI: InChI=1S/C16H21NO5/c1-3-11(2)16(20)22-13-5-8-17-7-4-12(15(13)17)10-21-14(19)6-9-18/h3-4,6,9,13,15,18H,5,7-8,10H2,1-2H3/b9-6-,11-3+/t13-,15-/m1/s1
• InChI Key: KREIPAAFIFMOKA-QXCUTPQZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.34 g/mol
• Exact Mass: 307.14197277 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9530	95.30%
Caco-2	+	0.6912	69.12%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7588	75.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9114	91.14%
OATP1B3 inhibitior	+	0.9431	94.31%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.5162	51.62%
P-glycoprotein inhibitior	-	0.7408	74.08%
P-glycoprotein substrate	-	0.6150	61.50%
CYP3A4 substrate	+	0.6001	60.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8263	82.63%
CYP3A4 inhibition	-	0.9410	94.10%
CYP2C9 inhibition	-	0.9259	92.59%
CYP2C19 inhibition	-	0.9152	91.52%
CYP2D6 inhibition	-	0.8304	83.04%
CYP1A2 inhibition	-	0.7374	73.74%
CYP2C8 inhibition	-	0.7965	79.65%
CYP inhibitory promiscuity	-	0.9411	94.11%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.4828	48.28%
Eye corrosion	-	0.9712	97.12%
Eye irritation	-	0.9729	97.29%
Skin irritation	-	0.7556	75.56%
Skin corrosion	-	0.9085	90.85%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8153	81.53%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.8441	84.41%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6354	63.54%
Acute Oral Toxicity (c)	III	0.5861	58.61%
Estrogen receptor binding	-	0.8411	84.11%
Androgen receptor binding	-	0.5613	56.13%
Thyroid receptor binding	-	0.6993	69.93%
Glucocorticoid receptor binding	-	0.5152	51.52%
Aromatase binding	-	0.7118	71.18%
PPAR gamma	-	0.8038	80.38%
Honey bee toxicity	-	0.8179	81.79%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6055	60.55%
Fish aquatic toxicity	-	0.6023	60.23%

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	98.33%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.59%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.09%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.66%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.62%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.39%	97.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.91%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.75%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.53%	93.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.51%	95.89%

Plants that contains it

• Alkanna orientalis

Cross-Links

• PubChem: 163071287
• LOTUS: LTS0022992
• wikiData: Q105144946