NP-MRD: Showing NP-Card for epi-lyfoline (NP0037210)

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Record Information

Version

2.0

Created at

2021-06-20 20:11:10 UTC

Updated at

2021-06-30 00:09:16 UTC

NP-MRD ID

NP0037210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epi-lyfoline

Provided By

JEOL Database JEOL Logo

Description

Lyfoline belongs to the class of organic compounds known as quinolizidines. Quinolizidines are compounds containing a quinolizidine moiety, which is a octahydro-2H-quinolizine derivative. epi-lyfoline is found in Heimia montana and Heimia salicifolia. epi-lyfoline was first documented in 2008 (PMID: 18374955). Based on a literature review very few articles have been published on Lyfoline.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122113D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202122113D          

 58 62  0  0  0  0            999 V2000
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    5.2685   -5.9890    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1266   -4.4322    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518   -3.7636    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -2.4905    3.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2122    0.2707    2.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4142   -3.6599    3.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4787    3.3707   -1.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034    1.5879   -3.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081   -0.4070   -4.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563   -2.8014   -3.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -4.3574   -0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148   -0.1432   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
 14 15  1  0  0  0  0
 12 20  1  0  0  0  0
 14 13  1  0  0  0  0
 14 44  1  1  0  0  0
 19 10  1  0  0  0  0
  3  2  1  0  0  0  0
 10 11  1  0  0  0  0
 20 21  1  0  0  0  0
 11 12  1  0  0  0  0
 21 22  2  0  0  0  0
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 21 23  1  0  0  0  0
 14 19  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 10  6  1  0  0  0  0
 30 28  2  0  0  0  0
  6  7  2  0  0  0  0
 28 27  1  0  0  0  0
 16 17  1  0  0  0  0
 27 26  2  0  0  0  0
  7  8  1  0  0  0  0
 26 25  1  0  0  0  0
 16 15  1  0  0  0  0
 25 31  2  0  0  0  0
 31 30  1  0  0  0  0
  5 30  1  0  0  0  0
  8  3  2  0  0  0  0
 28 29  1  0  0  0  0
 17 18  1  0  0  0  0
  8  9  1  0  0  0  0
  3  4  1  0  0  0  0
  2  1  1  0  0  0  0
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 15 45  1  0  0  0  0
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 10 38  1  6  0  0  0
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 11 40  1  0  0  0  0
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  7 36  1  0  0  0  0
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 23 53  1  0  0  0  0
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 31 58  1  0  0  0  0
 29 57  1  0  0  0  0
  9 37  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037210

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C2C3=C(O[H])C([H])=C([H])C(=C3[H])\C([H])=C([H])/C(=O)O[C@]3([H])C([H])([H])[C@]([H])(N4C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]4([H])C3([H])[H])C2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H27NO5/c1-30-24-14-18-19(13-23(24)28)21-12-17(11-16-4-2-3-9-26(16)21)31-25(29)8-6-15-5-7-22(27)20(18)10-15/h5-8,10,13-14,16-17,21,27-28H,2-4,9,11-12H2,1H3/b8-6-/t16-,17+,21+/m1/s1

> <INCHI_KEY>
CDTGNBVPXHNHGE-RDOPERODSA-N

> <FORMULA>
C25H27NO5

> <MOLECULAR_WEIGHT>
421.493

> <EXACT_MASS>
421.188922973

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.31785803938499

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13Z,17S,19R)-4,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.1^{8,12}.0^{2,7}.0^{19,24}]hexacosa-2,4,6,8,10,12(26),13-heptaen-15-one

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
4.025591097645081

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.818596867830998

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.966345359395786

> <JCHEM_PKA_STRONGEST_BASIC>
7.255753362124846

> <JCHEM_POLAR_SURFACE_AREA>
79.23

> <JCHEM_REFRACTIVITY>
118.87829999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13Z,17S,19R)-4,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.1^{8,12}.0^{2,7}.0^{19,24}]hexacosa-2,4,6,8,10,12(26),13-heptaen-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
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   -0.4504    1.4825   -0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0527    3.0067    0.6810 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    2.3645   -1.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652    1.3459   -2.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507   -0.0902   -2.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6766   -0.8588   -3.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076   -2.2134   -3.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792   -2.7986   -1.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2915   -4.1029   -1.6330 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764   -2.0615   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -0.7193   -1.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2685   -5.9890    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6570   -4.7492    4.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4142   -3.6599    3.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3325   -3.8376    1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8350   -3.5476    1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4787    3.3707   -1.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034    1.5879   -3.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3968   -4.3574   -0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148   -0.1432   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
  4  5  2  0
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  3  2  1  0
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 24 25  1  0
 10  6  1  0
 30 28  2  0
  6  7  2  0
 28 27  1  0
 16 17  1  0
 27 26  2  0
  7  8  1  0
 26 25  1  0
 16 15  1  0
 25 31  2  0
 31 30  1  0
  5 30  1  0
  8  3  2  0
 28 29  1  0
 17 18  1  0
  8  9  1  0
  3  4  1  0
  2  1  1  0
 16 47  1  0
 16 48  1  0
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 17 50  1  0
 18 51  1  0
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 15 45  1  0
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 10 38  1  6
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 31 58  1  0
 29 57  1  0
  9 37  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       4.561  -5.299   1.583  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.607  -4.919   2.568  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.636  -4.033   2.177  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.475  -3.500   0.899  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.429  -2.596   0.622  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.525  -2.226   1.661  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.703  -2.765   2.944  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.741  -3.656   3.183  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.877  -4.164   4.447  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.587  -1.208   1.402  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.117   0.183   1.863  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.981   1.239   1.174  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.430   0.754   1.019  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.800  -0.331   2.054  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.291  -0.696   1.903  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.628  -1.951   2.694  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.742  -3.123   2.274  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.526  -2.697   1.447  0.00  0.00           C+0
HETATM   19  N   UNK     0      -1.892  -1.511   2.033  0.00  0.00           N+0
HETATM   20  O   UNK     0      -0.450   1.482  -0.155  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.610   2.322  -0.229  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.053   3.007   0.681  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.194   2.365  -1.586  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.465   1.346  -2.422  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.251  -0.090  -2.201  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.677  -0.859  -3.219  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.408  -2.213  -3.014  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.679  -2.799  -1.780  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.292  -4.103  -1.633  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.276  -2.062  -0.746  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.616  -0.719  -1.005  0.00  0.00           C+0
HETATM   32  H   UNK     0       5.269  -5.989   2.052  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.080  -5.828   0.753  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.127  -4.432   1.226  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.152  -3.764   0.091  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.034  -2.490   3.756  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.657  -4.749   4.404  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.776  -1.179   0.323  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.943   0.345   1.643  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.212   0.271   2.954  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.972   2.171   1.754  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.597   0.371   0.003  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.102   1.615   1.121  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.685   0.115   3.052  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.913   0.137   2.253  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.545  -0.856   0.847  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.484  -1.754   3.764  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.684  -2.213   2.565  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.414  -3.660   3.173  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.332  -3.838   1.687  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.822  -2.505   0.407  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.835  -3.548   1.420  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.479   3.371  -1.880  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.903   1.588  -3.389  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.408  -0.407  -4.171  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.056  -2.801  -3.802  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.397  -4.357  -0.700  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.115  -0.143  -0.228  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3    1                                                       
CONECT    3    2    8    4                                                  
CONECT    4    5    3   35                                                  
CONECT    5    4    6   30                                                  
CONECT    6    5   10    7                                                  
CONECT    7    6    8   36                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   37                                                       
CONECT   10   19   11    6   38                                             
CONECT   11   10   12   39   40                                             
CONECT   12   20   11   13   41                                             
CONECT   13   14   12   42   43                                             
CONECT   14   15   13   44   19                                             
CONECT   15   14   16   45   46                                             
CONECT   16   17   15   47   48                                             
CONECT   17   16   18   49   50                                             
CONECT   18   19   17   51   52                                             
CONECT   19   18   10   14                                                  
CONECT   20   12   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   53                                                  
CONECT   24   23   25   54                                                  
CONECT   25   24   26   31                                                  
CONECT   26   27   25   55                                                  
CONECT   27   28   26   56                                                  
CONECT   28   30   27   29                                                  
CONECT   29   28   57                                                       
CONECT   30   28   31    5                                                  
CONECT   31   25   30   58                                                  
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    4                                                            
CONECT   36    7                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   29                                                            
CONECT   58   31                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  124    0
END

RDKit          3D

58 62  0  0  0  0  0  0  0  0999 V2000
    4.5605   -5.2990    1.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6068   -4.9192    2.5685 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6358   -4.0333    2.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4754   -3.4996    0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -2.5958    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5252   -2.2264    1.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033   -2.7647    2.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7412   -3.6561    3.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766   -4.1636    4.4475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5866   -1.2080    1.4017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1168    0.1829    1.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809    1.2394    1.1741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4299    0.7536    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002   -0.3310    2.0539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2912   -0.6960    1.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6278   -1.9511    2.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   -3.1232    2.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5258   -2.6970    1.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921   -1.5109    2.0325 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4504    1.4825   -0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6102    2.3216   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527    3.0067    0.6810 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    2.3645   -1.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652    1.3459   -2.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507   -0.0902   -2.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6766   -0.8588   -3.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076   -2.2134   -3.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792   -2.7986   -1.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2915   -4.1029   -1.6330 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764   -2.0615   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -0.7193   -1.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2685   -5.9890    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0799   -5.8280    0.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1266   -4.4322    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518   -3.7636    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -2.4905    3.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6570   -4.7492    4.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7762   -1.1786    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9431    0.3452    1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2122    0.2707    2.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719    2.1709    1.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5969    0.3712    0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1021    1.6151    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849    0.1147    3.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9126    0.1367    2.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5455   -0.8557    0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4840   -1.7535    3.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6841   -2.2127    2.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4142   -3.6599    3.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3325   -3.8376    1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8225   -2.5049    0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8350   -3.5476    1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4787    3.3707   -1.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034    1.5879   -3.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081   -0.4070   -4.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563   -2.8014   -3.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -4.3574   -0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148   -0.1432   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
  4  5  2  0
  5  6  1  0
 14 15  1  0
 12 20  1  0
 14 13  1  0
 14 44  1  1
 19 10  1  0
  3  2  1  0
 10 11  1  0
 20 21  1  0
 11 12  1  0
 21 22  2  0
 12 13  1  0
 21 23  1  0
 14 19  1  0
 23 24  2  0
 24 25  1  0
 10  6  1  0
 30 28  2  0
  6  7  2  0
 28 27  1  0
 16 17  1  0
 27 26  2  0
  7  8  1  0
 26 25  1  0
 16 15  1  0
 25 31  2  0
 31 30  1  0
  5 30  1  0
  8  3  2  0
 28 29  1  0
 17 18  1  0
  8  9  1  0
  3  4  1  0
  2  1  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 15 45  1  0
 15 46  1  0
 10 38  1  6
 11 39  1  0
 11 40  1  0
 12 41  1  1
 13 42  1  0
 13 43  1  0
  7 36  1  0
  4 35  1  0
 23 53  1  0
 24 54  1  0
 27 56  1  0
 26 55  1  0
 31 58  1  0
 29 57  1  0
  9 37  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₇NO₅

Average Mass

421.4930 Da

Monoisotopic Mass

421.18892 Da

IUPAC Name

(1S,13Z,17S,19R)-4,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.1^{8,12}.0^{2,7}.0^{19,24}]hexacosa-2,4,6,8,10,12(26),13-heptaen-15-one

Traditional Name

(1S,13Z,17S,19R)-4,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.1^{8,12}.0^{2,7}.0^{19,24}]hexacosa-2,4,6,8,10,12(26),13-heptaen-15-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C2C3=C(O[H])C([H])=C([H])C(=C3[H])\C([H])=C([H])/C(=O)O[C@]3([H])C([H])([H])[C@]([H])(N4C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]4([H])C3([H])[H])C2=C1[H]

InChI Identifier

InChI=1S/C25H27NO5/c1-30-24-14-18-19(13-23(24)28)21-12-17(11-16-4-2-3-9-26(16)21)31-25(29)8-6-15-5-7-22(27)20(18)10-15/h5-8,10,13-14,16-17,21,27-28H,2-4,9,11-12H2,1H3/b8-6-/t16-,17+,21+/m1/s1

InChI Key

CDTGNBVPXHNHGE-RDOPERODSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Heimia montana	LOTUS Database	35616633
Heimia salicifolia	JEOL database	Rumalla, C. S., et al, Phytochem. 69, 1756 (2008)

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
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Piperidine
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Lactone
Oxacycle
Azacycle
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Amine
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	3.54	ALOGPS
logP	4.03	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.97	ChemAxon
pKa (Strongest Basic)	7.26	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	118.88 m³·mol⁻¹	ChemAxon
Polarizability	45.32 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

4941436

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6436825

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rumalla CS, Jadhav AN, Smillie T, Fronczek FR, Khan IA: Alkaloids from Heimia salicifolia. Phytochemistry. 2008 May;69(8):1756-62. doi: 10.1016/j.phytochem.2008.01.028. Epub 2008 Mar 28. [PubMed:18374955 ]
Rumalla, C. S., et al. (2008). Rumalla, C. S., et al, Phytochem. 69, 1756 (2008). Phytochem..

Showing NP-Card for epi-lyfoline (NP0037210)

MOL for NP0037210 (epi-lyfoline)

3D MOL for NP0037210 (epi-lyfoline)

3D SDF for NP0037210 (epi-lyfoline)

3D-SDF for NP0037210 (epi-lyfoline)

PDB for NP0037210 (epi-lyfoline)

3D PDB for NP0037210 (epi-lyfoline)

SMILES for NP0037210 (epi-lyfoline)

INCHI for NP0037210 (epi-lyfoline)

Structure for NP0037210 (epi-lyfoline)

3D Structure for NP0037210 (epi-lyfoline)