D-Hyoscyamine

Basic Info

Common NameD-Hyoscyamine(F04808)
2D Structure
Description

Hyoscyamine is a plant toxin found in certain plants of the Solanaceae family, including henbane (Hyoscyamus niger), mandrake (Mandragora officinarum), jimsonweed (Datura stramonium), and deadly nightshade (Atropa belladonna). It is used as a drug to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in palliative care.(L1255)

FRCD IDF04808
CAS Number13269-35-7
PubChem CID637577
FormulaC17H23NO3
IUPAC Name

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate

InChI Key

RKUNBYITZUJHSG-QXULXFAOSA-N

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

Canonical SMILES

CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3

Isomeric SMILES

CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)[C@@H](CO)C3=CC=CC=C3

Synonyms
        
            (R)-atropine
        
            (+)-Atropine
        
            (+)-HYOSCYAMINE
        
            hyoscyamine
        
            tropan-3alpha-yl (2R)-3-hydroxy-2-phenylpropanoate
        
            (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2R)-3-hydroxy-2-phenylpropanoate
        
            UNII-V3203SI72M
        
            V3203SI72M
        
            [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate
        
            13269-35-7
Classifies
                

                  
                    Plant Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassAlkaloids and derivatives
ClassTropane alkaloids
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentTropane alkaloids
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsTropane alkaloid - Beta-hydroxy acid - Monocyclic benzene moiety - Hydroxy acid - Piperidine - Benzenoid - N-alkylpyrrolidine - Pyrrolidine - Amino acid or derivatives - Carboxylic acid ester - Tertiary aliphatic amine - Tertiary amine - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Azacycle - Organoheterocyclic compound - Organonitrogen compound - Amine - Hydrocarbon derivative - Organic oxide - Alcohol - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organic nitrogen compound - Primary alcohol - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.

Properties

Property NameProperty Value
Molecular Weight289.375
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Complexity353
Monoisotopic Mass289.168
Exact Mass289.168
XLogP1.8
Formal Charge0
Heavy Atom Count21
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9569
Human Intestinal AbsorptionHIA+0.9286
Caco-2 PermeabilityCaco2+0.8866
P-glycoprotein SubstrateSubstrate0.5000
P-glycoprotein InhibitorNon-inhibitor0.6542
Non-inhibitor0.8595
Renal Organic Cation TransporterInhibitor0.7956
Distribution
Subcellular localizationLysosome0.4825
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7041
CYP450 2D6 SubstrateNon-substrate0.6838
CYP450 3A4 SubstrateSubstrate0.5496
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9275
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9285
CYP450 3A4 InhibitorNon-inhibitor0.9500
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9113
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8354
Inhibitor0.5378
AMES ToxicityNon AMES toxic0.7742
CarcinogensNon-carcinogens0.9631
Fish ToxicityHigh FHMT0.8274
Tetrahymena Pyriformis ToxicityHigh TPT0.9314
Honey Bee ToxicityLow HBT0.5891
BiodegradationReady biodegradable0.5527
Acute Oral ToxicityIII0.7806
Carcinogenicity (Three-class)Non-required0.6945
Model Value Unit
Absorption
Aqueous solubility-1.8475LogS
Caco-2 Permeability1.1717LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7305LD50, mol/kg
Fish Toxicity1.0113pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7143pIGC50, ug/L

Targets

Target Details

Glycine receptor subunit alpha-1

General Function:
Transmitter-gated ion channel activity
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRA1
Uniprot ID:
P23415
Molecular Weight:
52623.35 Da
References
  1. Jensen AA, Kristiansen U: Functional characterisation of the human alpha1 glycine receptor in a fluorescence-based membrane potential assay. Biochem Pharmacol. 2004 May 1;67(9):1789-99. [15081878 ]
Target Details

Muscarinic acetylcholine receptor M4

General Function:
Guanyl-nucleotide exchange factor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular Weight:
53048.65 Da
Mechanism of Action:
Hyoscyamine is an anticholinergic, specifically an antimuscarinic, and works by blocking the action of acetylcholine at parasympathetic sites in smooth muscle, secretory glands, and the central nervous system.
References
  1. Lanzafame AA, Sexton PM, Christopoulos A: Interaction studies of multiple binding sites on m4 muscarinic acetylcholine receptors. Mol Pharmacol. 2006 Aug;70(2):736-46. Epub 2006 May 18. [16709648 ]
Target Details

Muscarinic acetylcholine receptor M3

General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
Mechanism of Action:
Hyoscyamine is an anticholinergic, specifically an antimuscarinic, and works by blocking the action of acetylcholine at parasympathetic sites in smooth muscle, secretory glands, and the central nervous system.
References
  1. Nelson CP, Gupta P, Napier CM, Nahorski SR, Challiss RA: Functional selectivity of muscarinic receptor antagonists for inhibition of M3-mediated phosphoinositide responses in guinea pig urinary bladder and submandibular salivary gland. J Pharmacol Exp Ther. 2004 Sep;310(3):1255-65. Epub 2004 May 12. [15140916 ]
Target Details

Muscarinic acetylcholine receptor M5

General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM5
Uniprot ID:
P08912
Molecular Weight:
60073.205 Da
Mechanism of Action:
Hyoscyamine is an anticholinergic, specifically an antimuscarinic, and works by blocking the action of acetylcholine at parasympathetic sites in smooth muscle, secretory glands, and the central nervous system.
References
  1. Wikipedia. Hyoscyamine. Last Updated 10 June 2009. : http://en.wikipedia.org/wiki/Hyoscyamine
Target Details

Muscarinic acetylcholine receptor M2

General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol.
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
Mechanism of Action:
Hyoscyamine is an anticholinergic, specifically an antimuscarinic, and works by blocking the action of acetylcholine at parasympathetic sites in smooth muscle, secretory glands, and the central nervous system.
References
  1. Nelson CP, Gupta P, Napier CM, Nahorski SR, Challiss RA: Functional selectivity of muscarinic receptor antagonists for inhibition of M3-mediated phosphoinositide responses in guinea pig urinary bladder and submandibular salivary gland. J Pharmacol Exp Ther. 2004 Sep;310(3):1255-65. Epub 2004 May 12. [15140916 ]
Target Details

Muscarinic acetylcholine receptor M1

General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
Mechanism of Action:
Hyoscyamine is an anticholinergic, specifically an antimuscarinic, and works by blocking the action of acetylcholine at parasympathetic sites in smooth muscle, secretory glands, and the central nervous system.
References
  1. Wikipedia. Hyoscyamine. Last Updated 10 June 2009. : http://en.wikipedia.org/wiki/Hyoscyamine