NP-MRD: Showing NP-Card for (+)-atropine (NP0293620)

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Record Information

Version

2.0

Created at

2022-09-10 01:43:30 UTC

Updated at

2022-09-10 01:43:30 UTC

NP-MRD ID

NP0293620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-atropine

Description

(R)-atropine 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. (+)-atropine is found in Mandragora officinarum. Based on a literature review very few articles have been published on (R)-atropine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
   -4.6360    1.7253    1.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4067    1.0234    0.8239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2458   -0.1693    1.6165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2173   -1.1491    0.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1317   -0.7994   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3746    0.5098   -0.5226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9350    0.3311   -0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1090    0.1006    0.3292 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0470   -0.6018   -0.0588 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289   -0.1427    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895    0.9604    0.6856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579   -0.9672   -0.3142 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4304   -1.2173   -1.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890   -0.0207   -2.4965 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7185   -0.2591    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6897   -0.8974    0.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8804   -0.2969    1.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1228    0.9904    0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1826    1.6526   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    1.0263   -0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513   -0.7068    1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8317    1.7412    2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4840    2.7802    0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4507    1.3148    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4469   -0.0142    2.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2290   -1.0097    1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8553   -2.1982    1.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6680   -1.5849   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1861   -0.6641   -0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991    1.2483   -1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893   -0.4550   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917    1.3244   -1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8150    1.0567    0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526   -1.9648    0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -1.6926   -2.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2365   -1.9139   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6126    0.3921   -2.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801   -1.9119    1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105   -0.8387    1.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0349    1.4804    0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3219    2.6753   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2578    1.5589   -0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2537   -0.6550    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8564   -1.7614    1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 21  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6  2  1  0
 20 15  1  0
 21  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  1
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  1
 21 43  1  0
 21 44  1  0
 12 34  1  1
 13 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END


  Mrv1652309102203432D          

 21 23  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
   -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  1  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
  6  2  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  8 21  1  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0293620

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
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-JJXSEGSLSA-N

> <FORMULA>
C17H23NO3

> <MOLECULAR_WEIGHT>
289.375

> <EXACT_MASS>
289.167793605

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.535696932565976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.571241016666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.145740617562414

> <JCHEM_PKA_STRONGEST_BASIC>
9.3855618707585

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
80.81640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(+)-atropine

> <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  C   UNK     0      -2.087   6.945   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.616   6.492   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.657   7.359   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.990   6.589   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.990   5.049   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.657   4.279   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.324   4.279   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.658   5.049   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.991   4.279   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.324   2.739   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.658   1.969   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.658   0.429   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.324  -0.341   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.990   0.429   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.990   1.969   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.772   8.895   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(+)-Atropine	ChEBI
(+)-Hyoscyamine	ChEBI

Chemical Formula

C₁₇H₂₃NO₃

Average Mass

289.3750 Da

Monoisotopic Mass

289.16779 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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-JJXSEGSLSA-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
Mandragora officinarum	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
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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate (CHEBI:48882 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21865610

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

48882

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (+)-atropine (NP0293620)

MOL for NP0293620 ((+)-atropine)

3D MOL for NP0293620 ((+)-atropine)

3D SDF for NP0293620 ((+)-atropine)

3D-SDF for NP0293620 ((+)-atropine)

PDB for NP0293620 ((+)-atropine)

3D PDB for NP0293620 ((+)-atropine)

SMILES for NP0293620 ((+)-atropine)

INCHI for NP0293620 ((+)-atropine)

Structure for NP0293620 ((+)-atropine)

3D Structure for NP0293620 ((+)-atropine)