NP-MRD: Showing NP-Card for Dihydrodeoxycernuine (NP0069823)

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Record Information

Version

2.0

Created at

2022-04-28 15:09:11 UTC

Updated at

2022-04-28 15:09:11 UTC

NP-MRD ID

NP0069823

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrodeoxycernuine

Description

(3Aalpha,6abeta,7abeta,12aalpha)-Tetradecahydro-5alpha-methyl-2H-pyrido[1',2':3,4]Pyrimido[2,1,6-de]quinolizine belongs to the class of organic compounds known as quinolizidines. Quinolizidines are compounds containing a quinolizidine moiety, which is a octahydro-2H-quinolizine derivative. Dihydrodeoxycernuine is found in Lycopodium carolinianum var. affine. Based on a literature review very few articles have been published on (3aalpha,6abeta,7abeta,12aalpha)-Tetradecahydro-5alpha-methyl-2H-pyrido[1',2':3,4]Pyrimido[2,1,6-de]quinolizine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
    4.2299    1.5065    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3098    0.6959   -0.0783 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1261   -0.6901    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7515   -1.2265    0.4132 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5212   -2.1308   -0.8020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0955   -2.5774   -0.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5770   -2.2729    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5646   -0.7602    0.8097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6830   -0.1970    0.1948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9247   -0.7360    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104    0.3714    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0130    1.3066   -0.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7065    1.7485   -0.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5643    0.8156   -0.7330 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3418    1.6748   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349    0.7024   -0.5058 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0818    1.4902   -0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7070   -0.2679    0.5137 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0782    1.0598    1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8996    2.5513    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2687    1.4805    0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8669    0.6561   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7698   -1.4131   -0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669   -0.7387    1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -1.9218    1.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8165   -1.6267   -1.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992   -2.9995   -0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5171   -2.0519   -1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039   -3.6558   -0.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1667   -2.8418    1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6391   -2.5736    0.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168   -0.6963    1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299   -1.3067    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3166   -1.4534   -0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9046   -0.0826    0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6078    0.9012    1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6614    0.8024   -1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6364    2.1784   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8513    1.9550   -2.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4939    2.7730   -0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790    0.3646   -1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884    1.9722    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460    2.5326   -1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832    0.3122   -1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8985    2.1836    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876    2.1861   -1.1782 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  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 17  2  1  0
 18  4  1  0
 18  8  1  0
 14  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  1
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  1
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  6
 15 42  1  0
 15 43  1  0
 16 44  1  6
 17 45  1  0
 17 46  1  0
M  END


  Mrv1652304282217092D          

 18 21  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    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
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   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
    2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    2.1434    2.0625    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  8  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 12 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0069823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@H]2CCC[C@@H]3N4CCCC[C@H]4C[C@@H](C1)N23

> <INCHI_IDENTIFIER>
InChI=1S/C16H28N2/c1-12-9-14-6-4-7-16-17-8-3-2-5-13(17)11-15(10-12)18(14)16/h12-16H,2-11H2,1H3/t12-,13-,14-,15+,16+/m0/s1

> <INCHI_KEY>
YURLNPVZEVJTQP-RFBLXINOSA-N

> <FORMULA>
C16H28N2

> <MOLECULAR_WEIGHT>
248.414

> <EXACT_MASS>
248.22524891

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
30.7181874743981

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,7S,9R,11S,13S)-11-methyl-2,17-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecane

> <ALOGPS_LOGP>
3.94

> <JCHEM_LOGP>
3.2118440893333324

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.560496889734112

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
75.7368

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,7S,9R,11S,13S)-11-methyl-2,17-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   17                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    7                                                       
CONECT   18   12                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
(3Aalpha,6abeta,7abeta,12aalpha)-tetradecahydro-5a-methyl-2H-pyrido[1',2':3,4]pyrimido[2,1,6-de]quinolizine	Generator
(3Aalpha,6abeta,7abeta,12aalpha)-tetradecahydro-5α-methyl-2H-pyrido[1',2':3,4]pyrimido[2,1,6-de]quinolizine	Generator

Chemical Formula

C₁₆H₂₈N₂

Average Mass

248.4140 Da

Monoisotopic Mass

248.22525 Da

IUPAC Name

(1R,7S,9R,11S,13S)-11-methyl-2,17-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecane

Traditional Name

(1R,7S,9R,11S,13S)-11-methyl-2,17-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecane

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H]2CCC[C@@H]3N4CCCC[C@H]4C[C@@H](C1)N23

InChI Identifier

InChI=1S/C16H28N2/c1-12-9-14-6-4-7-16-17-8-3-2-5-13(17)11-15(10-12)18(14)16/h12-16H,2-11H2,1H3/t12-,13-,14-,15+,16+/m0/s1

InChI Key

YURLNPVZEVJTQP-RFBLXINOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Lycopodium carolinianum var. affine	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolizidines. Quinolizidines are compounds containing a quinolizidine moiety, which is a octahydro-2H-quinolizine derivative.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolizidines

Sub Class

Not Available

Direct Parent

Quinolizidines

Alternative Parents

Substituents

Quinolizidine
Pyridopyrimidine
Pyrimidine
Pyridine
Piperidine
1,3-diazinane
Azacycle
Aminal
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
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	3.94	ALOGPS
logP	3.21	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	7.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.74 m³·mol⁻¹	ChemAxon
Polarizability	30.72 Å³	ChemAxon
Number of Rings	4	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

101102778

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dihydrodeoxycernuine (NP0069823)

MOL for NP0069823 (Dihydrodeoxycernuine)

3D MOL for NP0069823 (Dihydrodeoxycernuine)

3D SDF for NP0069823 (Dihydrodeoxycernuine)

3D-SDF for NP0069823 (Dihydrodeoxycernuine)

PDB for NP0069823 (Dihydrodeoxycernuine)

3D PDB for NP0069823 (Dihydrodeoxycernuine)

SMILES for NP0069823 (Dihydrodeoxycernuine)

INCHI for NP0069823 (Dihydrodeoxycernuine)

Structure for NP0069823 (Dihydrodeoxycernuine)

3D Structure for NP0069823 (Dihydrodeoxycernuine)