Scopalamine

Details

• Internal ID: 0f01beb0-915b-44c4-8226-368d517c5500
• Taxonomy: Organic acids and derivatives > Hydroxy acids and derivatives > Beta hydroxy acids and derivatives
• IUPAC Name: [(1R,2R,4S,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] 3-hydroxy-2-phenylpropanoate
• SMILES (Canonical): CN1C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4
• SMILES (Isomeric): CN1[C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)C(CO)C4=CC=CC=C4
• InChI: InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11?,12?,13-,14+,15-,16+
• InChI Key: STECJAGHUSJQJN-QBMZJCKTSA-N
• Popularity: 7,574 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.35 g/mol
• Exact Mass: 303.14705815 g/mol
• Topological Polar Surface Area (TPSA): 62.30 Ų
• XlogP: 0.90

Synonyms

• (-)-Scopolamine
• scopolamine
• Atroscine
• 138-12-5
• (+)-Scopolamine
• [(1S,2S,4R,5R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] 3-hydroxy-2-phenylpropanoate
• Scopolaminhydrobromid
• (+)-Hyoscine
• Benzeneacetic acid, alpha-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2,4))non-7-yl ester, (1alpha,2beta,4beta,5alpha,7beta)-(+-)-
• (+/-)-Scopolamine
• 51-34-3
• tropic acid ester with scopine
• HSDB 4074
• EINECS 200-090-3
• SCHEMBL6840787
• 6-beta,7-beta-epoxy-1-alpha H,5-alpha H-tropan-3-alpha-ol (-)-tropate
• DTXSID8043812
• SCHEMBL24175406
• STECJAGHUSJQJN-QBMZJCKTSA-N
• STECJAGHUSJQJN-SDODBCEQSA-N
• Benzeneacetic acid, .alpha.-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, [7(R)-(1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)]-
• AKOS015955512
• EN300-28336725
• W-105903
• (1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0,2,4]nonan-7-yl 3-hydroxy-2-phenylpropanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	1.514 nM	IC50	via Super-PRED
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	3.02 nM	Ki	via Super-PRED
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	6.5 nM	Ki	via Super-PRED
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	0.5754 nM	IC50	via Super-PRED
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	1.288 nM	Ki	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	125.9 nM	Potency	via Super-PRED

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	94.65%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.64%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.94%	86.33%
CHEMBL4040	P28482	MAP kinase ERK2	86.43%	83.82%
CHEMBL5028	O14672	ADAM10	85.81%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.72%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	84.08%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.41%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.22%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.69%	89.00%
CHEMBL4208	P20618	Proteasome component C5	80.04%	90.00%

Plants that contains it

• Atropa belladonna
• Datura innoxia
• Datura metel
• Datura stramonium
• Datura stramonium
• Hyoscyamus niger
• Linum usitatissimum
• Scopolia carniolica
• Scopolia japonica

Cross-Links

• PubChem: 6451257
• NPASS: NPC117351
• LOTUS: LTS0142014
• wikiData: Q104391779