(-)-Scopolamine

Details

• Internal ID: cf34af25-cf5c-4766-8685-c166ebfbda85
• Taxonomy: Organic acids and derivatives > Hydroxy acids and derivatives > Beta hydroxy acids and derivatives
• IUPAC Name: (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): CN1C2CC(CC1C3C2O3)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
• InChI Key: STECJAGHUSJQJN-UHFFFAOYSA-N
• Popularity: 7,610 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
• Atomic LogP (AlogP): 0.92
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• (-)-Scopolamine
• 51-34-3
• Atroscine
• CHEMBL13030
• 138-12-5
• (+)-Scopolamine
• (+)-Hyoscine
• Benzeneacetic acid, .alpha.-(hydroxymethyl)-, (1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, (.alpha.S)-
• 9-methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl tropate
• tropic acid ester with scopine
• HSDB 4074
• Atroscin
• Plexonal
• EINECS 200-090-3
• 9-methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl 3-hydroxy-2-phenylpropanoate
• NSC61806
• SCHEMBL16227
• 6-.beta.,7-.beta.-Epoxy-3-.alpha.-tropanyl S-(-)-tropate
• ChEMBL_11434
• MLS006012038
• 3-Oxa-9-azatricyclo(3.3.1.O(2,4))nonan-7-ol, 9-methyl-, tropate
• 6-beta,7-beta-epoxy-1-alpha H,5-alpha H-tropan-3-alpha-ol (-)-tropate
• 9-Methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]nonan-7-ol (-)-tropate
• Tropic acid, 9-methyl-3-oxa-9-azatricyclo(3.3.1.O(2,4))non-7-yl ester
• CHEBI:91541
• DTXSID60858963
• 1.alpha.H,5.alpha.H-Tropan-3.alpha.-ol, 6.beta.,7.beta.-epoxy-, (-)-tropate (ester)
• STECJAGHUSJQJN-UHFFFAOYSA-N
• Benzeneacetic acid, .alpha.-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl ester, [7(S)-(1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)]-
• BBL033894
• BDBM50015720
• STL377948
• AKOS001581155
• AKOS016038549
• NCGC00015932-03
• NCGC00162334-01
• SMR001307730
• VS-12336
• LS-144660
• AB00826823-11
• L001096
• BRD-A14566392-004-03-5
• 81D34684-E0B2-4B3A-A36C-FB916BBC90F7
• 9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl tropate
• 9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2),?]nonan-7-yl 3-hydroxy-2-phenylpropanoate
• 9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl 3-hydroxy-2-phenylpropanoate
• (hyoscine)3-Hydroxy-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.0*2,4*]non-7-yl ester
• (S)-(1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl 3-hydroxy-2-phenylpropanoate
• [(1S,2S,4R,5S)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate
• 475199-31-6
• Benzotropine3-Hydroxy-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.0*2,4*]non-7-yl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.9714	97.14%
Subcellular localzation	Lysosomes	0.5921	59.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9449	94.49%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	-	0.7557	75.57%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	+	0.5353	53.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3936	39.36%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9270	92.70%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9801	98.01%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6988	69.88%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9787	97.87%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7261	72.61%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	1.0000	100.00%
skin sensitisation	-	0.8585	85.85%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8857	88.57%
Acute Oral Toxicity (c)	III	0.7702	77.02%
Estrogen receptor binding	-	0.8431	84.31%
Androgen receptor binding	-	0.6130	61.30%
Thyroid receptor binding	-	0.7747	77.47%
Glucocorticoid receptor binding	-	0.7911	79.11%
Aromatase binding	-	0.6418	64.18%
PPAR gamma	+	0.5707	57.07%
Honey bee toxicity	-	0.9122	91.22%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5855	58.55%
Fish aquatic toxicity	-	0.6915	69.15%

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

• Anisodus tanguticus
• Atropa belladonna
• Atropanthe sinensis
• Brugmansia arborea
• Brugmansia sanguinea
• Datura ferox
• Datura innoxia
• Datura metel
• Datura stramonium
• Datura stramonium
• Duboisia hopwoodii
• Duboisia leichhardtii
• Duboisia myoporoides
• Hyoscyamus albus
• Hyoscyamus niger
• Hyoscyamus pusillus
• Linum usitatissimum
• Mandragora officinarum
• Physochlaina alaica
• Scopolia carniolica
• Scopolia japonica
• Solandra grandiflora

Cross-Links

• PubChem: 5184
• NPASS: NPC233910
• ChEMBL: CHEMBL13030
• LOTUS: LTS0213778
• wikiData: Q105260197