(2R,3R)-4-[[(7R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methoxy]-3-propan-2-ylpent-4-ene-2,3-diol

Details

• Internal ID: 9d4ad613-4c2f-420c-9550-581fa9ddb2f1
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: (2R,3R)-4-[[(7R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methoxy]-3-propan-2-ylpent-4-ene-2,3-diol
• SMILES (Canonical): CC(C)C(C(C)O)(C(=C)OCC1=CCN2C1C(CC2)O)O
• SMILES (Isomeric): C[C@H]([C@](C(C)C)(C(=C)OCC1=CCN2C1[C@@H](CC2)O)O)O
• InChI: InChI=1S/C16H27NO4/c1-10(2)16(20,11(3)18)12(4)21-9-13-5-7-17-8-6-14(19)15(13)17/h5,10-11,14-15,18-20H,4,6-9H2,1-3H3/t11-,14-,15?,16-/m1/s1
• InChI Key: LCGFFVMHSUIPAC-XKAGKQMDSA-N
• Popularity: 0 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): 73.20 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.66
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9085	90.85%
Caco-2	+	0.5961	59.61%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5786	57.86%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.8920	89.20%
OATP1B3 inhibitior	+	0.9456	94.56%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6911	69.11%
P-glycoprotein inhibitior	-	0.9391	93.91%
P-glycoprotein substrate	-	0.5157	51.57%
CYP3A4 substrate	+	0.5674	56.74%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	+	0.4280	42.80%
CYP3A4 inhibition	-	0.9761	97.61%
CYP2C9 inhibition	-	0.8860	88.60%
CYP2C19 inhibition	-	0.8664	86.64%
CYP2D6 inhibition	-	0.7382	73.82%
CYP1A2 inhibition	-	0.8837	88.37%
CYP2C8 inhibition	-	0.8461	84.61%
CYP inhibitory promiscuity	-	0.9697	96.97%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Danger	0.5641	56.41%
Eye corrosion	-	0.9780	97.80%
Eye irritation	-	0.9724	97.24%
Skin irritation	-	0.7436	74.36%
Skin corrosion	-	0.8983	89.83%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6987	69.87%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.9625	96.25%
skin sensitisation	-	0.7954	79.54%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6692	66.92%
Acute Oral Toxicity (c)	III	0.4282	42.82%
Estrogen receptor binding	-	0.7207	72.07%
Androgen receptor binding	-	0.5697	56.97%
Thyroid receptor binding	-	0.6070	60.70%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5359	53.59%
PPAR gamma	-	0.6256	62.56%
Honey bee toxicity	-	0.8883	88.83%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.6858	68.58%

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	99.36%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.06%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.58%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.29%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.25%	91.11%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.71%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.50%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.16%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.76%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.59%	95.89%
CHEMBL238	Q01959	Dopamine transporter	82.45%	95.88%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.23%	100.00%
CHEMBL5028	O14672	ADAM10	80.00%	97.50%

Plants that contains it

• Cynoglossum amabile

Cross-Links

• PubChem: 6428028
• NPASS: NPC304683