(+)-Hyoscyamine

Details

• Internal ID: f13abc10-9b97-49fa-bcc5-5ca218b48669
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate
• SMILES (Canonical): CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
• SMILES (Isomeric): CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)[C@@H](CO)C3=CC=CC=C3
• InChI: InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15?,16-/m0/s1
• InChI Key: RKUNBYITZUJHSG-QXULXFAOSA-N
• Popularity: 26,969 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.40 g/mol
• Exact Mass: 289.16779360 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• (R)-atropine
• (+)-Atropine
• 13269-35-7
• Hyoscyamine, (+)-
• CHEMBL3084476
• V3203SI72M
• R-(+)-Hyoscyamine
• UNII-V3203SI72M
• tropan-3alpha-yl (2R)-3-hydroxy-2-phenylpropanoate
• Hyoscyamine (D)-
• (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2R)-3-hydroxy-2-phenylpropanoate
• [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate
• 5-21-01-00235 (Beilstein Handbook Reference)
• HSDB 3553
• d-hyoscyamine
• BRN 0091258
• BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, 8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, (3(R)-ENDO)-
• HYOSCYAMINE, D-
• Prestwick0_000233
• Prestwick1_000233
• Prestwick2_000233
• Lopac-A-0257
• Lopac-H-9002
• ATROPINE, (R)-
• SCHEMBL25020
• SPBio_002226
• CHEMBL1379091
• CHEBI:48882
• DTXSID201045952
• HMS1568P07
• Atropine dried down 100 microg/mL
• Benzeneacetic acid, alpha-(hydroxymethyl)-, 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, (3(R)-endo)-
• TNP00272
• Atropine 1.0 mg/ml in Acetonitrile
• BDBM50469864
• [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate
• Atropine 100 microg/mL in Acetonitrile
• NCGC00015026-01
• NCGC00015026-02
• NCGC00016359-01
• NCGC00017333-01
• CAS-101-31-5
• PD132959
• Q27121382
• [(1s,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl](2r)-3-hydroxy-2-phenylpropanoate
• BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, (.ALPHA.R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9762	97.62%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Lysosomes	0.4825	48.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9541	95.41%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	1.0000	100.00%
BSEP inhibitior	-	0.8666	86.66%
P-glycoprotein inhibitior	-	0.9389	93.89%
P-glycoprotein substrate	-	0.7721	77.21%
CYP3A4 substrate	+	0.5662	56.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3762	37.62%
CYP3A4 inhibition	-	0.9500	95.00%
CYP2C9 inhibition	-	0.9275	92.75%
CYP2C19 inhibition	-	0.9285	92.85%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9813	98.13%
CYP inhibitory promiscuity	-	0.9113	91.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6945	69.45%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9761	97.61%
Skin irritation	-	0.8242	82.42%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6189	61.89%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	1.0000	100.00%
skin sensitisation	-	0.9029	90.29%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8448	84.48%
Acute Oral Toxicity (c)	III	0.7806	78.06%
Estrogen receptor binding	-	0.7539	75.39%
Androgen receptor binding	-	0.6929	69.29%
Thyroid receptor binding	-	0.8320	83.20%
Glucocorticoid receptor binding	-	0.8661	86.61%
Aromatase binding	-	0.7444	74.44%
PPAR gamma	+	0.5318	53.18%
Honey bee toxicity	-	0.9334	93.34%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	-	0.5515	55.15%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	0.44 nM; 0.25 nM; 0.2692 nM	Ki; Ki; Ki	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	0.8128 nM; 2.818 nM; 0.912 nM	Ki; Ki; Ki	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	0.5 nM; 0.2692 nM; 0.53 nM; 3.2 nM	Ki; Ki; Ki; IC50	via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	0.34 nM; 0.64 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	0.14 nM; 0.21 nM; 0.6 nM	Ki; Ki; Ki	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	10000 nM; 10000 nM; 4466.8 nM; 4466.8 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.65%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.13%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.58%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.62%	86.33%
CHEMBL5028	O14672	ADAM10	85.25%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	85.24%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.57%	97.09%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	84.38%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.45%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.31%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.67%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.19%	82.69%

Plants that contains it

• Atropa belladonna
• Datura metel
• Datura stramonium
• Hyoscyamus albus
• Hyoscyamus niger
• Linum usitatissimum
• Lycium barbarum
• Lycium chinense
• Scopolia carniolica
• Scopolia japonica

Cross-Links

• PubChem: 637577
• NPASS: NPC169485
• ChEMBL: CHEMBL1379091
• LOTUS: LTS0057506
• wikiData: Q104393164