Tropanserin

Details

• Internal ID: 263c8fe8-c889-44f7-b8a8-aeef7260241d
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Benzoic acid esters
• IUPAC Name: [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3,5-dimethylbenzoate
• SMILES (Canonical): CC1=CC(=CC(=C1)C(=O)OC2CC3CCC(C2)N3C)C
• SMILES (Isomeric): CC1=CC(=CC(=C1)C(=O)OC2C[C@H]3CC[C@@H](C2)N3C)C
• InChI: InChI=1S/C17H23NO2/c1-11-6-12(2)8-13(7-11)17(19)20-16-9-14-4-5-15(10-16)18(14)3/h6-8,14-16H,4-5,9-10H2,1-3H3/t14-,15+,16?
• InChI Key: HDDNYFLPWFSBLN-XYPWUTKMSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₃NO₂
• Molecular Weight: 273.37 g/mol
• Exact Mass: 273.172878976 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 85181-40-4
• Tropanserine
• Tropyl 3,5-dimethylbenzoate
• Tropanserina
• Tropanserinum
• tropanyl 3,5-dimethylbenzoate
• 04B48I6VHR
• DTXSID0042618
• CHEBI:64142
• [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3,5-dimethylbenzoate
• TROPANYL-3,5-DIMETHYLBENZOATE
• Benzoic acid, 3,5-dimethyl-, 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, endo-
• Benzoic acid,3,5-dimethyl-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
• Tropanserine [French]
• Tropanserinum [Latin]
• Tropanserina [Spanish]
• Tropanserin [INN:BAN]
• (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3,5-dimethylbenzoate
• rel-(1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-yl 3,5-dimethylbenzoate
• MDL 72422
• UNII-04B48I6VHR
• NCGC00024703-02
• (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3,5-dimethylbenzoate
• Tocris-0641
• MDL72422;MDL-72422;MDL 72422
• endo-8-Methyl-8-azabicyclo(3.2.1)oct-3-yl 3,5-dimethylbenzoate
• TROPANSERIN [INN]
• CHEMBL1476871
• CHEMBL1742402
• DTXCID8022618
• Tox21_110918
• NCGC00024703-01
• NCGC00186620-01
• PD071090
• CAS-85181-40-4
• Q7845609
• (1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl3,5-dimethylbenzoate
• (1R,5S)-8-METHYL-8-AZABICYCLO[3.2.1]OCTAN-3-YL 3,5-DIMETHYLBENZOATE
• BENZOIC ACID, 3,5-DIMETHYL-, (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9746	97.46%
Caco-2	+	0.8081	80.81%
Blood Brain Barrier	+	0.8108	81.08%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4795	47.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9153	91.53%
OATP1B3 inhibitior	+	0.9454	94.54%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.8500	85.00%
BSEP inhibitior	-	0.6922	69.22%
P-glycoprotein inhibitior	-	0.9090	90.90%
P-glycoprotein substrate	-	0.7712	77.12%
CYP3A4 substrate	+	0.5658	56.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4206	42.06%
CYP3A4 inhibition	-	0.8718	87.18%
CYP2C9 inhibition	-	0.9266	92.66%
CYP2C19 inhibition	-	0.9319	93.19%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	-	0.8677	86.77%
CYP2C8 inhibition	-	0.9508	95.08%
CYP inhibitory promiscuity	-	0.9231	92.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6309	63.09%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.7888	78.88%
Skin irritation	-	0.8074	80.74%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4331	43.31%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8995	89.95%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8144	81.44%
Acute Oral Toxicity (c)	III	0.6159	61.59%
Estrogen receptor binding	-	0.8150	81.50%
Androgen receptor binding	-	0.8200	82.00%
Thyroid receptor binding	-	0.6314	63.14%
Glucocorticoid receptor binding	-	0.6816	68.16%
Aromatase binding	-	0.7190	71.90%
PPAR gamma	-	0.5520	55.20%
Honey bee toxicity	-	0.9391	93.91%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6455	64.55%
Fish aquatic toxicity	-	0.3806	38.06%

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	95.83%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.03%	98.95%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	92.12%	100.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	90.97%	97.53%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.93%	97.21%
CHEMBL340	P08684	Cytochrome P450 3A4	90.88%	91.19%
CHEMBL4208	P20618	Proteasome component C5	88.59%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.47%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.94%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.86%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.69%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.24%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.24%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	82.67%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.65%	89.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.82%	90.24%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.40%	95.89%

Plants that contains it

• Alibertia edulis
• Aniba rosaeodora
• Calycophyllum spruceanum
• Conchocarpus heterophyllus
• Cupania vernalis
• Emmotum nitens
• Goniorrhachis marginata
• Iryanthera polyneura
• Neoraputia alba
• Porcelia macrocarpa
• Rhodostemonodaphne miranda
• Sextonia rubra
• Spiranthera odoratissima
• Vellozia candida
• Vellozia compacta
• Zanthoxylum petiolare

Cross-Links

• PubChem: 68600
• LOTUS: LTS0197777
• wikiData: Q105109443