[(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2-methylbutanoate

Details

• Internal ID: 12f06573-3cf1-47a6-acc0-f2187197cd49
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OCC1=CCN2C1C(CC2)OC(=O)C(=CC)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)OCC1=CCN2[C@H]1[C@H](CC2)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C18H27NO4/c1-5-12(3)17(20)22-11-14-7-9-19-10-8-15(16(14)19)23-18(21)13(4)6-2/h6-7,12,15-16H,5,8-11H2,1-4H3/b13-6-/t12-,15+,16-/m1/s1
• InChI Key: HCWYTYBGRVJHCP-CWAPYDSKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₇NO₄
• Molecular Weight: 321.40 g/mol
• Exact Mass: 321.19400834 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9658	96.58%
Caco-2	+	0.6939	69.39%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5920	59.20%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8896	88.96%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.5916	59.16%
P-glycoprotein inhibitior	-	0.7333	73.33%
P-glycoprotein substrate	-	0.6091	60.91%
CYP3A4 substrate	+	0.5588	55.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7961	79.61%
CYP3A4 inhibition	-	0.8287	82.87%
CYP2C9 inhibition	-	0.9067	90.67%
CYP2C19 inhibition	-	0.8537	85.37%
CYP2D6 inhibition	-	0.7570	75.70%
CYP1A2 inhibition	-	0.6587	65.87%
CYP2C8 inhibition	-	0.8559	85.59%
CYP inhibitory promiscuity	-	0.8161	81.61%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Danger	0.4388	43.88%
Eye corrosion	-	0.9759	97.59%
Eye irritation	-	0.9734	97.34%
Skin irritation	-	0.7725	77.25%
Skin corrosion	-	0.9127	91.27%
Ames mutagenesis	-	0.6554	65.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6962	69.62%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.9625	96.25%
skin sensitisation	-	0.8264	82.64%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5067	50.67%
Acute Oral Toxicity (c)	III	0.6814	68.14%
Estrogen receptor binding	-	0.8633	86.33%
Androgen receptor binding	-	0.4857	48.57%
Thyroid receptor binding	-	0.5843	58.43%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.8154	81.54%
PPAR gamma	-	0.7964	79.64%
Honey bee toxicity	-	0.8274	82.74%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6255	62.55%
Fish aquatic toxicity	+	0.7510	75.10%

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	98.97%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.09%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.12%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.98%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.35%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.06%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.35%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.38%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.54%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.55%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.13%	89.62%

Plants that contains it

• Cynoglossum creticum

Cross-Links

• PubChem: 162865484
• LOTUS: LTS0128211
• wikiData: Q105026029