Talpinine

Details

• Internal ID: 6279066f-6d07-4f5c-ac4a-a61ba8354677
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: (2S,13S,15R,16R,19S,20R,21R)-11,19-dimethyl-18-oxa-1,11-diazahexacyclo[11.8.0.02,16.04,12.05,10.015,20]henicosa-4(12),5,7,9-tetraen-21-ol
• SMILES (Canonical): CC1C2C3CC4C5=C(CC(C3CO1)N4C2O)C6=CC=CC=C6N5C
• SMILES (Isomeric): C[C@H]1[C@H]2[C@@H]3C[C@H]4C5=C(C[C@@H]([C@@H]3CO1)N4[C@@H]2O)C6=CC=CC=C6N5C
• InChI: InChI=1S/C20H24N2O2/c1-10-18-12-7-17-19-13(11-5-3-4-6-15(11)21(19)2)8-16(14(12)9-24-10)22(17)20(18)23/h3-6,10,12,14,16-18,20,23H,7-9H2,1-2H3/t10-,12+,14+,16-,17-,18-,20+/m0/s1
• InChI Key: UTKWZPZEAKXURV-QYEMIGNBSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.183778013 g/mol
• Topological Polar Surface Area (TPSA): 37.60 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.45
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• CHEMBL3338251

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9798	97.98%
Caco-2	+	0.8369	83.69%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4809	48.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9054	90.54%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.7051	70.51%
P-glycoprotein inhibitior	-	0.8447	84.47%
P-glycoprotein substrate	+	0.7039	70.39%
CYP3A4 substrate	+	0.6648	66.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7492	74.92%
CYP3A4 inhibition	-	0.8545	85.45%
CYP2C9 inhibition	-	0.9176	91.76%
CYP2C19 inhibition	-	0.7362	73.62%
CYP2D6 inhibition	-	0.7682	76.82%
CYP1A2 inhibition	-	0.5729	57.29%
CYP2C8 inhibition	-	0.5912	59.12%
CYP inhibitory promiscuity	-	0.8005	80.05%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6542	65.42%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9904	99.04%
Skin irritation	-	0.8129	81.29%
Skin corrosion	-	0.9429	94.29%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7248	72.48%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.5887	58.87%
skin sensitisation	-	0.8867	88.67%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8890	88.90%
Acute Oral Toxicity (c)	III	0.5725	57.25%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.6216	62.16%
Thyroid receptor binding	+	0.6255	62.55%
Glucocorticoid receptor binding	-	0.6422	64.22%
Aromatase binding	-	0.5743	57.43%
PPAR gamma	-	0.5764	57.64%
Honey bee toxicity	-	0.8338	83.38%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	-	0.4211	42.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	97.34%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.07%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.71%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.59%	89.00%
CHEMBL2581	P07339	Cathepsin D	92.57%	98.95%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	91.90%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	90.61%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.79%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.69%	86.33%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.61%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.43%	97.25%
CHEMBL5805	Q9NR97	Toll-like receptor 8	83.21%	96.25%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	81.89%	98.46%
CHEMBL255	P29275	Adenosine A2b receptor	81.18%	98.59%

Plants that contains it

• Alstonia angustifolia

Cross-Links

• PubChem: 11834305
• LOTUS: LTS0214817
• wikiData: Q105278855