NP-MRD: Showing NP-Card for 1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate (NP0268449)

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Record Information

Version

2.0

Created at

2022-09-08 13:34:15 UTC

Updated at

2022-09-08 13:34:15 UTC

NP-MRD ID

NP0268449

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate

Description

Alpha-Belladonnine, also known as α-belladonnine, belongs to the class of organic compounds known as naphthalenecarboxylic acids and derivatives. Naphthalenecarboxylic acids and derivatives are compounds containing a naphthalene moiety, which bears a carboxylic acid group or a derivative at one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. Based on a literature review very few articles have been published on alpha-Belladonnine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082215342D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309082215342D          

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   -1.9012    1.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2436    0.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3402    2.1886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8705    2.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198    1.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020    1.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288   -4.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 24 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 15 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 12 39  1  0  0  0  0
  8 40  1  0  0  0  0
  3 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0268449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2CCC1CC(C2)OC(=O)[C@H]1CCC(C(=O)OC2CC3CCC(C2)N3C)(C2=CC=CC=C2)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C34H42N2O4/c1-35-23-12-13-24(35)19-27(18-23)39-32(37)30-16-17-34(22-8-4-3-5-9-22,31-11-7-6-10-29(30)31)33(38)40-28-20-25-14-15-26(21-28)36(25)2/h3-11,23-28,30H,12-21H2,1-2H3/t23?,24?,25?,26?,27?,28?,30-,34?/m0/s1

> <INCHI_KEY>
GERIGMSHTUAXSI-YJRMYWFWSA-N

> <FORMULA>
C34H42N2O4

> <MOLECULAR_WEIGHT>
542.72

> <EXACT_MASS>
542.31445784

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
61.226046915475145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4S)-1-phenyl-1,2,3,4-tetrahydronaphthalene-1,4-dicarboxylate

> <JCHEM_LOGP>
4.956870902666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.686592504402588

> <JCHEM_POLAR_SURFACE_AREA>
59.080000000000005

> <JCHEM_REFRACTIVITY>
154.69869999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4S)-1-phenyl-3,4-dihydro-2H-naphthalene-1,4-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.858  -7.202   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -8.667   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.396  -9.100   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564 -10.304   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104 -10.304   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.064  -9.100   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.721  -7.598   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.677   1.180   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.204   2.627   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.161   0.912   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.829   2.092   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.196   3.496   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.898   4.866   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.408   5.171   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.587   4.181   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.549   2.642   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.321   1.712   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -2.502   4.085   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -3.492   5.265   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.657   1.180   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.131   2.627   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.120   3.807   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.637   3.539   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.164   2.092   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.174   0.912   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.054  -7.598   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   40                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   40                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   39                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   28   34                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   19                                                       
CONECT   26   24   21   27                                                  
CONECT   27   26                                                            
CONECT   28   15   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   15   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34   12                                                  
CONECT   40    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Value	Source
a-Belladonnine	Generator
Α-belladonnine	Generator

Chemical Formula

C₃₄H₄₂N₂O₄

Average Mass

542.7200 Da

Monoisotopic Mass

542.31446 Da

IUPAC Name

1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4S)-1-phenyl-1,2,3,4-tetrahydronaphthalene-1,4-dicarboxylate

Traditional Name

1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4S)-1-phenyl-3,4-dihydro-2H-naphthalene-1,4-dicarboxylate

CAS Registry Number

Not Available

SMILES

CN1C2CCC1CC(C2)OC(=O)[C@H]1CCC(C(=O)OC2CC3CCC(C2)N3C)(C2=CC=CC=C2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C34H42N2O4/c1-35-23-12-13-24(35)19-27(18-23)39-32(37)30-16-17-34(22-8-4-3-5-9-22,31-11-7-6-10-29(30)31)33(38)40-28-20-25-14-15-26(21-28)36(25)2/h3-11,23-28,30H,12-21H2,1-2H3/t23?,24?,25?,26?,27?,28?,30-,34?/m0/s1

InChI Key

GERIGMSHTUAXSI-YJRMYWFWSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenecarboxylic acids and derivatives. Naphthalenecarboxylic acids and derivatives are compounds containing a naphthalene moiety, which bears a carboxylic acid group or a derivative at one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthalenecarboxylic acids and derivatives

Direct Parent

Naphthalenecarboxylic acids and derivatives

Alternative Parents

Substituents

1-naphthalenecarboxylic acid or derivatives
Tetralin
Tropane alkaloid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen compound
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	4.96	ChemAxon
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	59.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	154.7 m³·mol⁻¹	ChemAxon
Polarizability	61.23 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101614997

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate (NP0268449)

MOL for NP0268449 (1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate)

3D MOL for NP0268449 (1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate)

3D SDF for NP0268449 (1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate)

3D-SDF for NP0268449 (1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate)

PDB for NP0268449 (1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate)

3D PDB for NP0268449 (1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate)

SMILES for NP0268449 (1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate)

INCHI for NP0268449 (1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate)

Structure for NP0268449 (1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate)

3D Structure for NP0268449 (1,4-bis({8-methyl-8-azabicyclo[3.2.1]octan-3-yl}) (4s)-1-phenyl-3,4-dihydro-2h-naphthalene-1,4-dicarboxylate)