NP-MRD: Showing NP-Card for (1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate (NP0303523)

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Record Information

Version

2.0

Created at

2022-09-10 17:56:13 UTC

Updated at

2022-09-10 17:56:13 UTC

NP-MRD ID

NP0303523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

Description

Anisodamine 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. (1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate is found in Anisodus tanguticus. (1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate was first documented in 2020 (PMID: 33633726). Based on a literature review a significant number of articles have been published on anisodamine (PMID: 36087820) (PMID: 34967033) (PMID: 35892780) (PMID: 35915796) (PMID: 35636257) (PMID: 35601065).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -2.8913    2.3920   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159    1.1326   -0.4696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5094    0.2579    0.6302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2921   -0.6172    0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2148   -0.1727   -0.1424 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0333   -0.8929    0.0027 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492   -0.2992    0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    0.9330    0.6315 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832   -1.0780    0.5488 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7493   -1.7903   -0.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433   -0.8474   -1.7897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5329   -0.2640    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1967   -0.5957    2.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771    0.1165    2.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428    1.2118    1.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921    1.5643    0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0003    0.8346    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7410   -0.1680   -1.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1589    0.3178   -1.5827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1442   -0.8398   -1.3465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2183   -0.7481   -2.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6033   -0.6837    0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0707    2.6809   -1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5429    2.6291    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6955    3.1631   -0.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8360    0.7628    1.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717   -0.4391    1.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -1.6873    0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9982    0.8851    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -1.8885    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9811   -2.5356   -1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7137   -2.3200   -0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -1.2739   -2.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485   -1.4670    2.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7817   -0.1621    3.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5965    1.8003    2.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4369    2.4246    0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826    1.1018   -0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0797    0.4898   -2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7217   -1.1749   -2.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522    0.8032   -2.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -1.7748   -1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0727    0.0464   -2.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6061   -1.6398    0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5963   -0.1875    0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 22  1  0
 22 20  1  0
 20 21  1  0
 20 19  1  0
 19 18  1  0
 18  5  1  0
  5  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 19  2  1  0
 17 12  1  0
  4  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  1
 22 44  1  0
 22 45  1  0
 20 42  1  1
 21 43  1  0
 19 41  1  6
 18 39  1  0
 18 40  1  0
  5 29  1  1
  4 27  1  0
  4 28  1  0
  9 30  1  1
 10 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END


  Mrv1652309102219562D          

 22 24  0  0  1  0            999 V2000
    0.3528    4.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542    4.4076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    5.3262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0072    5.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4197    4.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2424    4.5504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1183    3.7208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3299    3.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517    3.9423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0662    3.5298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0662    2.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517    2.2923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7807    2.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951    2.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2096    2.2923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7807    1.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951    1.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951    0.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7807   -0.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0662    0.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0662    1.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4134    4.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
  9 22  1  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@H]2CC(O)[C@@H]1C[C@@H](C2)OC(=O)C(CO)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
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?/m1/s1

> <INCHI_KEY>
WTQYWNWRJNXDEG-AQIKHJSRSA-N

> <FORMULA>
C17H23NO4

> <MOLECULAR_WEIGHT>
305.374

> <EXACT_MASS>
305.162708225

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.20136781863152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,5S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

> <JCHEM_LOGP>
0.4235434036666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.242167959533525

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.444837042780517

> <JCHEM_PKA_STRONGEST_BASIC>
8.842587954522479

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
82.13430000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.659   7.907   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.848   8.228   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.357   9.942   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.880   9.713   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.650   8.379   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.186   8.494   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.087   6.945   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.616   6.492   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.657   7.359   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.990   6.589   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.990   5.049   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.657   4.279   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.324   4.279   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.658   5.049   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.991   4.279   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.324   2.739   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.658   1.969   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.658   0.429   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.324  -0.341   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.990   0.429   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.990   1.969   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.772   8.895   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22    9    3                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Anisodamine hydrobromide	MeSH
Racanisodamine	MeSH
6-Hydroxyhyoscyamine	MeSH

Chemical Formula

C₁₇H₂₃NO₄

Average Mass

305.3740 Da

Monoisotopic Mass

305.16271 Da

IUPAC Name

(1S,3R,5S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

Traditional Name

(1S,3R,5S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

CAS Registry Number

Not Available

SMILES

CN1[C@H]2CC(O)[C@@H]1C[C@@H](C2)OC(=O)C(CO)C1=CC=CC=C1

InChI Identifier

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?/m1/s1

InChI Key

WTQYWNWRJNXDEG-AQIKHJSRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anisodus tanguticus	LOTUS Database	35616633

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Tropane alkaloid
Beta-hydroxy acid
Benzenoid
N-alkylpyrrolidine
Piperidine
Hydroxy acid
Monocyclic benzene moiety
Pyrrolidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.42	ChemAxon
pKa (Strongest Acidic)	14.44	ChemAxon
pKa (Strongest Basic)	8.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.13 m³·mol⁻¹	ChemAxon
Polarizability	32.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002274

Chemspider ID

78432820

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Anisodamine

METLIN ID

Not Available

PubChem Compound

51026956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qiao M, Zhang L, Xu C, Huo X, Chang J, Su J: Chitosan and anisodamine enhance the immersion immune efficacy of inactivated Elizabethkingia miricola vaccine in black spotted frogs. Fish Shellfish Immunol. 2022 Nov;130:93-102. doi: 10.1016/j.fsi.2022.08.072. Epub 2022 Sep 8. [PubMed:36087820 ]
Wang B, Chen T, Wang A, Fang J, Wang J, Yao W, Wu Y: Anisodamine affects the pigmentation, mineral density, craniofacial area, and eye development in zebrafish embryos. J Appl Toxicol. 2022 Jun;42(6):1067-1077. doi: 10.1002/jat.4278. Epub 2021 Dec 29. [PubMed:34967033 ]
Vera-Baquero FL, Morante-Zarcero S, Sierra I: Evaluation of Thermal Degradation of Tropane and Opium Alkaloids in Gluten-Free Corn Breadsticks Samples Contaminated with Stramonium Seeds and Baked with Poppy Seeds under Different Conditions. Foods. 2022 Jul 23;11(15):2196. doi: 10.3390/foods11152196. [PubMed:35892780 ]
Wang J, Zhu Q, Zhang S, Wen L, Wang L: Observation of Clinical Efficacy of Anisodamine and Chlorpromazine in the Treatment of Intractable Hiccup after Stroke. Biomed Res Int. 2022 Jul 11;2022:6563193. doi: 10.1155/2022/6563193. eCollection 2022. [PubMed:35915796 ]
Wei W, Kong N, Liu MZ, Han T, Xu JF, Liu C: Anisodamine potently inhibits SARS-CoV-2 infection in vitro and targets its main protease. Biochem Biophys Res Commun. 2022 Aug 6;616:8-13. doi: 10.1016/j.bbrc.2022.05.024. Epub 2022 May 13. [PubMed:35636257 ]
Dong GJ, Yang J, Zhao X, Guo SB: Anisodamine hydrobromide ameliorates cardiac damage after resuscitation. Exp Ther Med. 2022 Jun;23(6):422. doi: 10.3892/etm.2022.11349. Epub 2022 May 3. [PubMed:35601065 ]
Wang C, Zhu D, Zhang J, Du Y: Homochiral iron-based gamma-cyclodextrin metal-organic framework for stereoisomer separation in the open tubular capillary electrochromatography. J Pharm Biomed Anal. 2022 Jun 5;215:114777. doi: 10.1016/j.jpba.2022.114777. Epub 2022 Apr 19. [PubMed:35462287 ]
Zhang Y, Song D, Peng Z, Wang R, Li K, Ren H, Sun X, Du N, Tang SC: Anisodamine Enhances Macrophage M2 Polarization through Suppressing G9a-Mediated Interferon Regulatory Factor 4 Silencing to Alleviate Lipopolysaccharide-Induced Acute Lung Injury. J Pharmacol Exp Ther. 2022 Jun;381(3):247-256. doi: 10.1124/jpet.121.001019. Epub 2022 Apr 5. [PubMed:35383125 ]
Honore PM, Redant S, Preseau T, Cismas BV, Kaefer K, Barreto Gutierrez L, Anane S, Attou R, Gallerani A, De Bels D: Anisodamine microcirulatory effects in septic shock: be aware of cardiac side effects. Crit Care. 2021 Dec 16;25(1):433. doi: 10.1186/s13054-021-03854-5. [PubMed:34915896 ]
Lyu SC, Wang J, Xu WL, Wang HX, Pan F, Jiang T, He Q, Lang R: Therapeutic Effect of Combining Anisodamine With Neostigmine on Local Scar Formation Following Roux-en-Y Choledochojejunostomy in a Novel Rat Model. Front Pharmacol. 2021 Sep 29;12:700050. doi: 10.3389/fphar.2021.700050. eCollection 2021. [PubMed:34658849 ]
Lin X, Chen H, Lin YN: The clinical efficacy and safety of atropine combined with omeprazole in the treatment of patients with acute gastritis: a systematic review and meta-analysis. Ann Palliat Med. 2021 Sep;10(9):9535-9543. doi: 10.21037/apm-21-1868. [PubMed:34628879 ]
Yu Y, Zhu C, Hong Y, Chen L, Huang Z, Zhou J, Tian X, Liu D, Ren B, Zhang C, Hu C, Wang X, Yin R, Gao Y, Zhang Z: Effectiveness of anisodamine for the treatment of critically ill patients with septic shock: a multicentre randomized controlled trial. Crit Care. 2021 Sep 27;25(1):349. doi: 10.1186/s13054-021-03774-4. [PubMed:34579741 ]
Cheng X, Liu Y, Wang Z, Qu L, Ning Z: Active Yeast but Not Henhouse Environment Affects Dropping Moisture Levels in Egg-Laying Hens. Animals (Basel). 2021 Jul 23;11(8):2179. doi: 10.3390/ani11082179. [PubMed:34438640 ]
Zhao X, Zhao B, Zhao Y, Zhang Y, Qian M: Protective effect of anisodamine on bleomycin-induced acute lung injury in immature rats via modulating oxidative stress, inflammation, and cell apoptosis by inhibiting the JAK2/STAT3 pathway. Ann Transl Med. 2021 May;9(10):859. doi: 10.21037/atm-21-1750. [PubMed:34164493 ]
Authors unspecified: Withdrawn: Anisodamine (654-2) inhibits inflammation to alleviate influenza A virus-induced acute lung injury. J Med Virol. 2021 Dec;93(12):6850. doi: 10.1002/jmv.27043. [PubMed:34076913 ]
Liu Z, Wang W, Luo J, Zhang Y, Zhang Y, Gan Z, Shen X, Zhang Y, Meng X: Anti-Apoptotic Role of Sanhuang Xiexin Decoction and Anisodamine in Endotoxemia. Front Pharmacol. 2021 Apr 21;12:531325. doi: 10.3389/fphar.2021.531325. eCollection 2021. [PubMed:33967742 ]
Zhang S, Xu X, Huang Y, Sun S, Jin C, Ji H, Sun D, Xia A: Anisodamine ameliorates ischemia/reperfusion-induced renal injury in rats through activation of the extracellular signal-regulated kinase (ERK) pathway and anti-apoptotic effect. Pharmazie. 2021 May 1;76(5):220-224. doi: 10.1691/ph.2021.1302. [PubMed:33964996 ]
Bai S, Wang X, Wu H, Chen T, Li X, Zhang L, Li X, Er L, Du R: Cardioprotective effect of anisodamine against ischemia/reperfusion injury through the mitochondrial ATP-sensitive potassium channel. Eur J Pharmacol. 2021 Jun 15;901:174095. doi: 10.1016/j.ejphar.2021.174095. Epub 2021 Apr 20. [PubMed:33862063 ]
Qin Z, Xiang K, Su DF, Sun Y, Liu X: Activation of the Cholinergic Anti-Inflammatory Pathway as a Novel Therapeutic Strategy for COVID-19. Front Immunol. 2021 Feb 8;11:595342. doi: 10.3389/fimmu.2020.595342. eCollection 2020. [PubMed:33633726 ]
LOTUS database [Link]

Showing NP-Card for (1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate (NP0303523)

MOL for NP0303523 ((1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate)

3D MOL for NP0303523 ((1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate)

3D SDF for NP0303523 ((1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate)

3D-SDF for NP0303523 ((1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate)

PDB for NP0303523 ((1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate)

3D PDB for NP0303523 ((1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate)

SMILES for NP0303523 ((1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate)

INCHI for NP0303523 ((1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate)

Structure for NP0303523 ((1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate)

3D Structure for NP0303523 ((1s,3r,5s)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate)