NP-MRD: Showing NP-Card for macrophylline A (NP0035734)

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Record Information

Version

2.0

Created at

2021-06-20 19:05:51 UTC

Updated at

2021-06-30 00:06:55 UTC

NP-MRD ID

NP0035734

Secondary Accession Numbers

None

Natural Product Identification

Common Name

macrophylline A

Provided By

JEOL Database JEOL Logo

Description

Macrophylline A belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. macrophylline A is found in Uncaria macrophylla. macrophylline A was first documented in 2011 (Wang, K., et al.). Based on a literature review very few articles have been published on Macrophylline A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121053D          

 64 67  0  0  0  0            999 V2000
    2.8482    2.7269    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8947    1.7294    1.4560 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6500    0.8127    1.5983 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4997   -0.1662    0.3891 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7236   -1.0113    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2931   -1.0315   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061   -0.3218   -2.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8138   -0.0670   -3.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111   -1.8608    1.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319   -2.3292    0.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278   -2.0473    2.1661 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2198   -2.8367    3.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436   -1.0446    0.5393 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.1537    1.3352    2.0441 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.3475   -1.7239    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -1.6689   -0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
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 14 13  1  0  0  0  0
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  4  3  1  0  0  0  0
  3 28  1  0  0  0  0
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 25 24  2  0  0  0  0
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M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
    2.8482    2.7269    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202121053D          

 64 67  0  0  0  0            999 V2000
    2.8482    2.7269    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8947    1.7294    1.4560 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.2931   -1.0315   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061   -0.3218   -2.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2436   -1.0446    0.5393 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.3199    1.6125    1.8576 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4115    2.4950    3.1222 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8805    1.7807    4.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0186    0.6882    4.9526 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1610   -1.0019   -3.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4275   -3.8479    2.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1336   -2.3614    3.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061   -2.9046    4.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -1.7239    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -1.6689   -0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0373    0.5092   -0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483    1.7050    3.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9104   -4.4778   -1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5593   -3.2484   -3.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1932   -0.8041   -3.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1728    0.4603   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599    2.2888    1.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382    2.9901    3.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1110    3.3193    2.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.2167    4.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0199    1.0218    5.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543    0.4606    5.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0  0  0  0
 13  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3 28  1  0  0  0  0
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  4  5  1  0  0  0  0
 18 19  1  1  0  0  0
  5  9  1  0  0  0  0
 25 24  2  0  0  0  0
  5  6  2  0  0  0  0
 18 14  1  0  0  0  0
  6  7  1  0  0  0  0
 24 23  1  0  0  0  0
  7  8  1  0  0  0  0
 23 22  2  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 27 26  2  0  0  0  0
 11 12  1  0  0  0  0
 26 25  1  0  0  0  0
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  4 39  1  6  0  0  0
 15 16  1  0  0  0  0
  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
  2  1  1  0  0  0  0
 27 22  1  0  0  0  0
 19 20  2  0  0  0  0
 22 21  1  0  0  0  0
 28 29  1  0  0  0  0
 21 19  1  0  0  0  0
 29 30  1  0  0  0  0
 18 27  1  0  0  0  0
 30 31  1  0  0  0  0
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 31 64  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035734

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C([H])C([H])=C([H])C([H])=C2[C@]2(C1=O)C([H])([H])C([H])([H])N1[C@@]2([H])C([H])([H])[C@]([H])(C(=C(\[H])OC([H])([H])[H])\C(=O)OC([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[H])[C@]1([H])C([H])([H])C(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H32N2O5/c1-5-16-17(18(14-31-3)23(29)32-4)13-22-25(10-11-27(22)21(16)12-15(2)28)19-8-6-7-9-20(19)26-24(25)30/h6-9,14,16-17,21-22H,5,10-13H2,1-4H3,(H,26,30)/b18-14+/t16-,17+,21+,22+,25-/m1/s1

> <INCHI_KEY>
VWNYHBABHBBFQC-QFEVCRBPSA-N

> <FORMULA>
C25H32N2O5

> <MOLECULAR_WEIGHT>
440.54

> <EXACT_MASS>
440.231122138

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.54416929469696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-2-[(3R,5'S,6'R,7'S,8'aS)-6'-ethyl-2-oxo-5'-(2-oxopropyl)-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
2.7138525456666653

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.49787273705212

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.16580205315919

> <JCHEM_PKA_STRONGEST_BASIC>
10.457857990959921

> <JCHEM_POLAR_SURFACE_AREA>
84.94

> <JCHEM_REFRACTIVITY>
122.01129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-2-[(3R,5'S,6'R,7'S,8'aS)-6'-ethyl-2-oxo-5'-(2-oxopropyl)-3',5',6',7',8',8'a-hexahydro-1H,2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
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    1.3025    0.4735   -0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
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 14 13  1  0
 13  4  1  0
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  3 28  1  0
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 19 20  2  0
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 28 59  1  6
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 29 60  1  0
 29 61  1  0
 31 62  1  0
 31 63  1  0
 31 64  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       2.848   2.727   0.306  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.895   1.729   1.456  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.650   0.813   1.598  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.500  -0.166   0.389  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.724  -1.011   0.066  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.293  -1.032  -1.153  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.806  -0.322  -2.221  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.814  -0.067  -3.197  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.411  -1.861   1.080  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.532  -2.329   0.934  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.628  -2.047   2.166  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.220  -2.837   3.198  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.244  -1.045   0.539  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.971  -0.144   0.720  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.838   0.702   1.917  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.154   1.335   2.044  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.152   0.231   1.684  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.330  -0.824   0.929  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.255  -2.139   1.754  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.855  -2.292   2.897  0.00  0.00           O+0
HETATM   21  N   UNK     0      -2.762  -3.158   0.955  0.00  0.00           N+0
HETATM   22  C   UNK     0      -3.186  -2.681  -0.273  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.750  -3.409  -1.299  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.111  -2.713  -2.454  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.903  -1.326  -2.551  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.329  -0.610  -1.496  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.971  -1.306  -0.353  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.320   1.613   1.858  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.412   2.495   3.122  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.881   1.781   4.378  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.019   0.688   4.953  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.940   2.102   4.923  0.00  0.00           O+0
HETATM   33  H   UNK     0       3.778   3.305   0.282  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.747   2.229  -0.661  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.025   3.438   0.421  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.053   2.284   2.387  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.794   1.113   1.343  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.829   0.201   2.491  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.303   0.474  -0.483  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.166  -1.633  -1.386  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.654   0.481  -2.756  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.161  -1.002  -3.650  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.374   0.553  -3.984  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.428  -3.848   2.834  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.134  -2.361   3.568  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.506  -2.905   4.023  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.348  -1.724   1.391  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.112  -1.669  -0.353  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.037   0.509  -0.164  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.348   1.705   3.055  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.262   2.172   1.342  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.967   0.651   1.084  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.598  -0.183   2.596  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.819  -4.115   1.270  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.910  -4.478  -1.220  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.559  -3.248  -3.288  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.193  -0.804  -3.461  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.173   0.460  -1.581  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.160   2.289   1.007  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.538   2.990   3.351  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.111   3.319   2.935  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.102  -0.217   4.348  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.020   1.022   5.007  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.354   0.461   5.969  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    3    1   36   37                                             
CONECT    3    4   28    2   38                                             
CONECT    4   13    3    5   39                                             
CONECT    5    4    9    6                                                  
CONECT    6    5    7   40                                                  
CONECT    7    6    8                                                       
CONECT    8    7   41   42   43                                             
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   44   45   46                                             
CONECT   13   14    4   47   48                                             
CONECT   14   13   18   49   15                                             
CONECT   15   14   16   28                                                  
CONECT   16   15   17   50   51                                             
CONECT   17   18   16   52   53                                             
CONECT   18   17   19   14   27                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   22   19   54                                                  
CONECT   22   23   27   21                                                  
CONECT   23   24   22   55                                                  
CONECT   24   25   23   56                                                  
CONECT   25   24   26   57                                                  
CONECT   26   27   25   58                                                  
CONECT   27   26   22   18                                                  
CONECT   28    3   29   15   59                                             
CONECT   29   28   30   60   61                                             
CONECT   30   29   31   32                                                  
CONECT   31   30   62   63   64                                             
CONECT   32   30                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    2                                                            
CONECT   37    2                                                            
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    6                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   21                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   26                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   31                                                            
CONECT   63   31                                                            
CONECT   64   31                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  134    0
END

RDKit          3D

64 67  0  0  0  0  0  0  0  0999 V2000
    2.8482    2.7269    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8947    1.7294    1.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2198   -2.8367    3.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436   -1.0446    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9033   -1.3258   -2.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3291   -0.6104   -1.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9706   -1.3062   -0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199    1.6125    1.8576 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4115    2.4950    3.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805    1.7807    4.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0186    0.6882    4.9526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9397    2.1018    4.9228 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778    3.3054    0.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    2.2295   -0.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0252    3.4375    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0534    2.2844    2.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7941    1.1130    1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8290    0.2013    2.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3025    0.4735   -0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1659   -1.6332   -1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6540    0.4806   -2.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1610   -1.0019   -3.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744    0.5527   -3.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4275   -3.8479    2.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1336   -2.3614    3.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061   -2.9046    4.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -1.7239    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -1.6689   -0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0373    0.5092   -0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483    1.7050    3.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2624    2.1717    1.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9674    0.6507    1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5980   -0.1834    2.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191   -4.1147    1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104   -4.4778   -1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5593   -3.2484   -3.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1932   -0.8041   -3.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1728    0.4603   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599    2.2888    1.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382    2.9901    3.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1110    3.3193    2.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.2167    4.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0199    1.0218    5.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543    0.4606    5.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13  4  1  0
  4  3  1  0
  3 28  1  0
 17 18  1  0
  4  5  1  0
 18 19  1  1
  5  9  1  0
 25 24  2  0
  5  6  2  0
 18 14  1  0
  6  7  1  0
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  9 10  2  0
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  8 42  1  0
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  2 36  1  0
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 31 64  1  0
M  END

View in JSmol

Synonyms

Value	Source
Macrophylline b	MeSH

Chemical Formula

C₂₅H₃₂N₂O₅

Average Mass

440.5400 Da

Monoisotopic Mass

440.23112 Da

IUPAC Name

methyl (2E)-2-[(3R,5'S,6'R,7'S,8'aS)-6'-ethyl-2-oxo-5'-(2-oxopropyl)-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl (2E)-2-[(3R,5'S,6'R,7'S,8'aS)-6'-ethyl-2-oxo-5'-(2-oxopropyl)-3',5',6',7',8',8'a-hexahydro-1H,2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]N1C2=C([H])C([H])=C([H])C([H])=C2[C@]2(C1=O)C([H])([H])C([H])([H])N1[C@@]2([H])C([H])([H])[C@]([H])(C(=C(\[H])OC([H])([H])[H])\C(=O)OC([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[H])[C@]1([H])C([H])([H])C(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C25H32N2O5/c1-5-16-17(18(14-31-3)23(29)32-4)13-22-25(10-11-27(22)21(16)12-15(2)28)19-8-6-7-9-20(19)26-24(25)30/h6-9,14,16-17,21-22H,5,10-13H2,1-4H3,(H,26,30)/b18-14+/t16-,17+,21+,22+,25-/m1/s1

InChI Key

VWNYHBABHBBFQC-QFEVCRBPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Uncaria macrophylla	JEOL database	Wang, K., et al, J. Nat. Prod. 74, 12 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indolizidines

Sub Class

Not Available

Direct Parent

Indolizidines

Alternative Parents

Substituents

Indole or derivatives
Dihydroindole
Indolizidine
Aralkylamine
Beta-aminoketone
Piperidine
N-alkylpyrrolidine
Benzenoid
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxylic acid ester
Ketone
Lactam
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organopnictogen compound
Organonitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolizines (CHEBI:70067 )

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	2.66	ALOGPS
logP	2.71	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	10.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.94 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.01 m³·mol⁻¹	ChemAxon
Polarizability	47.54 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

35518347

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50993824

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, K., et al. (2011). Wang, K., et al, J. Nat. Prod. 74, 12 (2011). J. Nat. Prod..

Showing NP-Card for macrophylline A (NP0035734)

MOL for NP0035734 (macrophylline A)

3D MOL for NP0035734 (macrophylline A)

3D SDF for NP0035734 (macrophylline A)

3D-SDF for NP0035734 (macrophylline A)

PDB for NP0035734 (macrophylline A)

3D PDB for NP0035734 (macrophylline A)

SMILES for NP0035734 (macrophylline A)

INCHI for NP0035734 (macrophylline A)

Structure for NP0035734 (macrophylline A)

3D Structure for NP0035734 (macrophylline A)