NP-MRD: Showing NP-Card for Lycopodium base R (NP0070070)

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Record Information

Version

2.0

Created at

2022-04-28 15:20:29 UTC

Updated at

2022-04-28 15:20:29 UTC

NP-MRD ID

NP0070070

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lycopodium base R

Description

(1R,3S,10S,11R,14S,15S,16R)-15-hydroxy-16-methyl-2,6-diazapentacyclo[8.7.0.0¹,⁶.0³,¹¹.0¹⁰,¹⁴]Heptadecan-12-one belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. Lycopodium base R is found in Lycopodium fawcettii. Based on a literature review very few articles have been published on (1R,3S,10S,11R,14S,15S,16R)-15-hydroxy-16-methyl-2,6-diazapentacyclo[8.7.0.0¹,⁶.0³,¹¹.0¹⁰,¹⁴]Heptadecan-12-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
    2.9913   -2.2154   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0512   -1.2347    0.6183 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6340   -1.6878    0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172   -0.7075   -0.0350 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0885   -0.5092   -1.4343 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287    0.5943   -1.8273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1309    0.0932   -2.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3182   -1.1758   -1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345   -1.2079   -0.0308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301   -0.9475    1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3224    0.4494    1.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091    0.9040    1.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566    0.6813    0.5143 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2597    1.0637    0.7098 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3447    2.4889    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    2.5848   -0.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    3.3942   -1.7508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162    1.5295   -0.6186 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2638    0.1608    0.0808 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5370    0.5656    0.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0308   -1.9408    0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7508   -3.2380    0.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9216   -2.1284   -1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510   -1.1940    1.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6015   -2.6185   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2456   -2.0309    1.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040   -1.3529   -1.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    1.1007   -2.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094    0.8294   -1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515   -0.1384   -3.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9318   -2.0157   -1.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893   -1.3831   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596   -1.6740    1.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5117   -1.0834    0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7778    0.4238    2.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9492    1.1636    1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4194    0.3030    2.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944    1.9744    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024    1.1058    1.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1557    3.2322    1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3403    2.6920   -0.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121    1.9204   -0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    0.2094   -1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0550    1.0198   -0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  1
  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
 13 12  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 19  2  1  0
  9  4  1  0
 18 13  1  0
 13  4  1  0
 18  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  6
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  1
 15 40  1  0
 15 41  1  0
 18 42  1  1
 19 43  1  6
 20 44  1  0
M  END


  Mrv1652304282217202D          

 20 24  0  0  1  0            999 V2000
    0.2789   -0.7245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0237   -1.4920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -0.6338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5547   -1.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448    0.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9668    0.4622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5493   -0.3060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1930   -1.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3512   -1.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1609   -0.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2312    0.4060    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3053    1.2781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4221    1.4192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8734    1.4171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2515    1.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    0.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475    1.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574    2.0395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379    0.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -0.0203    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  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
 11 10  1  6  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
  6 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 12 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  1  0  0  0
  1 20  1  0  0  0  0
 11 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070070

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@]23N[C@H]4CCN2CCC[C@@]32[C@H](CC(=O)[C@@H]42)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N2O2/c1-9-8-16-15-4-2-5-18(16)6-3-11(17-16)13(15)12(19)7-10(15)14(9)20/h9-11,13-14,17,20H,2-8H2,1H3/t9-,10-,11+,13-,14+,15+,16-/m1/s1

> <INCHI_KEY>
PMZBYFAPABEYMY-KLTLJBQXSA-N

> <FORMULA>
C16H24N2O2

> <MOLECULAR_WEIGHT>
276.38

> <EXACT_MASS>
276.183778021

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
29.885874912924283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,10S,11R,14S,15S,16R)-15-hydroxy-16-methyl-2,6-diazapentacyclo[8.7.0.0^{1,6}.0^{3,11}.0^{10,14}]heptadecan-12-one

> <ALOGPS_LOGP>
0.25

> <JCHEM_LOGP>
0.48460876366666716

> <ALOGPS_LOGS>
-0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.489841938559113

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.634878611546988

> <JCHEM_PKA_STRONGEST_BASIC>
8.348157402413774

> <JCHEM_POLAR_SURFACE_AREA>
52.57

> <JCHEM_REFRACTIVITY>
75.4586

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,10S,11R,14S,15S,16R)-15-hydroxy-16-methyl-2,6-diazapentacyclo[8.7.0.0^{1,6}.0^{3,11}.0^{10,14}]heptadecan-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       0.521  -1.352   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.044  -2.785   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.056  -1.183   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.902  -2.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.884   0.274   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.805   0.863   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.892  -0.571   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.227  -2.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.656  -2.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.300  -0.962   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.432   0.758   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.570   2.386   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.655   2.649   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.630   2.645   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.203   1.994   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.229   0.387   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.022   2.471   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.787   3.807   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.751   1.063   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.609  -0.038   0.000  0.00  0.00           C+0
CONECT    1    2    3   20                                                  
CONECT    2    1                                                            
CONECT    3    1    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11   14                                             
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12   20                                             
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    6                                                       
CONECT   15   13   16                                                       
CONECT   16   15    7                                                       
CONECT   17   12   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    1   11                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₄N₂O₂

Average Mass

276.3800 Da

Monoisotopic Mass

276.18378 Da

IUPAC Name

(1R,3S,10S,11R,14S,15S,16R)-15-hydroxy-16-methyl-2,6-diazapentacyclo[8.7.0.0^{1,6}.0^{3,11}.0^{10,14}]heptadecan-12-one

Traditional Name

(1R,3S,10S,11R,14S,15S,16R)-15-hydroxy-16-methyl-2,6-diazapentacyclo[8.7.0.0^{1,6}.0^{3,11}.0^{10,14}]heptadecan-12-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@]23N[C@H]4CCN2CCC[C@@]32[C@H](CC(=O)[C@@H]42)[C@H]1O

InChI Identifier

InChI=1S/C16H24N2O2/c1-9-8-16-15-4-2-5-18(16)6-3-11(17-16)13(15)12(19)7-10(15)14(9)20/h9-11,13-14,17,20H,2-8H2,1H3/t9-,10-,11+,13-,14+,15+,16-/m1/s1

InChI Key

PMZBYFAPABEYMY-KLTLJBQXSA-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 fawcettii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Quinolidine
Azaspirodecane
Dihydroindole
Indole or derivatives
Azepane
Piperidine
1,3-diazinane
Pyrrolidine
Cyclic alcohol
Secondary alcohol
Ketone
Azacycle
Secondary amine
Secondary aliphatic amine
Aminal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	0.25	ALOGPS
logP	0.48	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	14.63	ChemAxon
pKa (Strongest Basic)	8.35	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.57 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.46 m³·mol⁻¹	ChemAxon
Polarizability	29.89 Å³	ChemAxon
Number of Rings	5	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

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

163105539

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lycopodium base R (NP0070070)

MOL for NP0070070 (Lycopodium base R)

3D MOL for NP0070070 (Lycopodium base R)

3D SDF for NP0070070 (Lycopodium base R)

3D-SDF for NP0070070 (Lycopodium base R)

PDB for NP0070070 (Lycopodium base R)

3D PDB for NP0070070 (Lycopodium base R)

SMILES for NP0070070 (Lycopodium base R)

INCHI for NP0070070 (Lycopodium base R)

Structure for NP0070070 (Lycopodium base R)

3D Structure for NP0070070 (Lycopodium base R)