Natural Product (NP) Details

General Information of the NP (ID: NP2556)
Name
Anisodamine
Synonyms
anisodamine; UNII-01343Q8EL8; 01343Q8EL8; 6-Hydroxy hyoscyamine; 55869-99-3; 6-Hydroxyhyoscyamine; 654-II; (Z)-RACANISODAMINE; CHEMBL2165224; HY-N0584; ZINC3197739; AKOS015955736; CCG-221772; CS-4549; DB11785; MCULE-3459933530; Hyoscyamine, 6-hydroxy- (6CI, 7CI); NCGC00485098-01; NCGC00485098-02; UNII-QQZ59S1DUT component WTQYWNWRJNXDEG-RBZJEDDUSA-N; (S)-3-hydroxy-2-phenyl-propionic acid (1r,3s,5r,6S)-6-hydroxy-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester, AldrichCPR; [(1R,3S,5R,6S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate; alpha-(Hydroxymethyl)benzeneacetic acid 6-hydroxy-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester; Benzeneacetic acid, alpha-(hydroxymethyl)-, (1R,3S,5R,6S)-6-hydroxy-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, (alphaS)-; Benzeneacetic acid, alpha-(hydroxymethyl)-, 6-hydroxy-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, (1R-(1-alpha,3-beta(S*),5-alpha,6-alpha))-
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Species Origin Solanaceae ...     Click to Show/Hide
Solanaceae
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Solanales
Family: Solanaceae
Disease Central and peripheral nervous disease [ICD-11: 8A04-8E7Z] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.947
 
MDCK Permeability
 -4.896
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 0.298
 
PPB
 28.5%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 +++
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - - -
HLM Stability
 - - -
 
Excretion
CLplasma
 12.916
 
T1/2
 2.256
Toxicity
DILI
 - -
 
Rat Oral Acute Toxicity
 - -
 
FDAMDD
 ++
 
Respiratory
 +
 
Human Hepatotoxicity
 ++
 
Ototoxicity
 +
 
Drug-induced Nephrotoxicity
 +
 
Drug-induced Neurotoxicity
 ++
 
Hematotoxicity
 - -
 
Genotoxicity
 +
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C17H23NO4
PubChem CID
6918612
Canonical SMILES
CN1C2CC(CC1C(C2)O)OC(=O)C(CO)C3=CC=CC=C3
InChI
1S/C17H23NO4/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3/t12-,13-,14+,15+,16-/m0/s1
InChIKey
WTQYWNWRJNXDEG-RBZJEDDUSA-N
CAS Number
CAS 55869-99-3
Herb ID
HBIN016189
SymMap ID
SMIT00605
TCMSP ID
MOL005409
TTD Drug ID
D06VFO
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Neostigmine      Myasthenia gravis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression JAK-2  Molecule Info 
Pathway MAP
Up-regulation Expression STAT3  Molecule Info 
Pathway MAP
                    In-vivo Model SD rats (250-270 g), C57BL/6 mice (25-30 g), and rabbits (2-3 kg) CS models were used in this study.
                    Experimental
                    Result(s)		 Ani/Neo combination could produce therapeutic effects in CS.
Target and Pathway
Target(s) Adrenergic receptor beta-1 (ADRB1)  Molecule Info  [3]
KEGG Pathway Calcium signaling pathway Click to Show/Hide
2 cGMP-PKG signaling pathway
3 cAMP signaling pathway
4 Neuroactive ligand-receptor interaction
5 Endocytosis
6 Adrenergic signaling in cardiomyocytes
7 Gap junction
8 Salivary secretion
9 Dilated cardiomyopathy
Panther Pathway Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway Click to Show/Hide
2 Beta1 adrenergic receptor signaling pathway
Pathwhiz Pathway Muscle/Heart Contraction Click to Show/Hide
Reactome Adrenoceptors Click to Show/Hide
2 G alpha (s) signalling events
WikiPathways Monoamine GPCRs Click to Show/Hide
2 Calcium Regulation in the Cardiac Cell
3 GPCRs, Class A Rhodopsin-like
4 Endothelin Pathways
5 GPCR ligand binding
6 GPCR downstream signaling
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 Combined administration of anisodamine and neostigmine rescued acute lethal crush syndrome through Alpha7nAChR-dependent JAK2-STAT3 signaling. Sci Rep. 2016 Nov 22;6:37709.
Reference 3 Medicinal plants in therapy. Bull World Health Organ. 1985;63(6):965-81.
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