NP-MRD: Showing NP-Card for 3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate (NP0239532)

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Record Information

Version

2.0

Created at

2022-09-06 23:09:23 UTC

Updated at

2022-09-06 23:09:23 UTC

NP-MRD ID

NP0239532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate

Description

3-Methyl-13λ⁵-azatricyclo[7.3.1.0⁵,¹³]Tridec-2-en-13-one belongs to the class of organic compounds known as 9b-azaphenalenes. These are alkaloids with a structure based on the perhydro-9b-azaphenalene skeleton. Perhydro-9b-azaphenalene is a tricyclic compound consisting of quinolizidine that share its only nitrogen atom with a piperidine. In some 9b-azaphenalenes, the resulting tricyclic backbone can be unsaturated. 3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate is found in Anatis ocellata. 3-Methyl-13λ⁵-azatricyclo[7.3.1.0⁵,¹³]Tridec-2-en-13-one is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    3.8490    0.6681   -0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4145    0.5210   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5835    1.5166   -0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1622    1.3176    0.0304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7792    2.2870   -0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1147    2.1524    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1745    0.7158    0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -0.1844   -0.4183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1259   -1.5444   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2868   -2.6196    0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1493   -2.3327    0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4904   -0.8936    0.6359 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9831   -0.7314    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -0.0748   -0.3445 N   0  0  2  0  0  4  0  0  0  0  0  0
    0.4084   -0.3205   -1.5744 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.4111   -0.2698   -0.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3199    1.5072    0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9647    0.9787   -1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8693    2.4349   -0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1320    1.4334    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094    2.0862   -1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827    3.2964   -0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1658    2.8815    1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9596    2.2663   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204    0.3665    0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6748    0.6178    1.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8761    0.3035   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193   -1.4686    0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4304   -1.8815   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3598   -3.5761   -0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7268   -2.8991    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5717   -2.9187    1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7798   -2.6549   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -0.6366    1.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574   -1.5892    0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3577   -0.7553    1.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  6
 13  2  1  0
 14  4  1  0
 14  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  6
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  1
 13 35  1  0
 13 36  1  0
M  CHG  2  14   1  15  -1
M  END


  Mrv1533004241506592D          

 15 17  0  0  0  0            999 V2000
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  CHG  2  14   1  15  -1
M  END
> <DATABASE_ID>
NP0239532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2CCCC3CCCC(C1)[N+]23[O-]

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO/c1-10-8-12-6-2-4-11-5-3-7-13(9-10)14(11,12)15/h8,11-13H,2-7,9H2,1H3

> <INCHI_KEY>
LJUPKMWFUIBDDA-UHFFFAOYSA-N

> <FORMULA>
C13H21NO

> <MOLECULAR_WEIGHT>
207.317

> <EXACT_MASS>
207.1623143

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.554470738044774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
1.8335409623333327

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.2254910405254953

> <JCHEM_POLAR_SURFACE_AREA>
23.06

> <JCHEM_REFRACTIVITY>
62.714200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    2                                                       
CONECT   14   12    4    8   15                                             
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₁NO

Average Mass

207.3170 Da

Monoisotopic Mass

207.16231 Da

IUPAC Name

3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate

Traditional Name

3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate

CAS Registry Number

Not Available

SMILES

CC1=CC2CCCC3CCCC(C1)[N+]23[O-]

InChI Identifier

InChI=1S/C13H21NO/c1-10-8-12-6-2-4-11-5-3-7-13(9-10)14(11,12)15/h8,11-13H,2-7,9H2,1H3

InChI Key

LJUPKMWFUIBDDA-UHFFFAOYSA-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
Anatis ocellata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9b-azaphenalenes. These are alkaloids with a structure based on the perhydro-9b-azaphenalene skeleton. Perhydro-9b-azaphenalene is a tricyclic compound consisting of quinolizidine that share its only nitrogen atom with a piperidine. In some 9b-azaphenalenes, the resulting tricyclic backbone can be unsaturated.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

9b-azaphenalenes

Sub Class

Not Available

Direct Parent

9b-azaphenalenes

Alternative Parents

Substituents

9b-azaphenalene skeleton
Quinolizidine
Piperidine
Trialkyl amine oxide
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
N-oxide
Hydrocarbon derivative
Organic salt
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organic cation
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.76	ALOGPS
logP	1.83	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	3.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	62.71 m³·mol⁻¹	ChemAxon
Polarizability	24.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate (NP0239532)

MOL for NP0239532 (3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate)

3D MOL for NP0239532 (3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate)

3D SDF for NP0239532 (3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate)

3D-SDF for NP0239532 (3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate)

PDB for NP0239532 (3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate)

3D PDB for NP0239532 (3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate)

SMILES for NP0239532 (3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate)

INCHI for NP0239532 (3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate)

Structure for NP0239532 (3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate)

3D Structure for NP0239532 (3-methyl-13-azatricyclo[7.3.1.0⁵,¹³]tridec-2-en-13-ium-13-olate)