NP-MRD: Showing NP-Card for macrodaphniphyllamine (NP0032559)

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Record Information

Version

2.0

Created at

2021-06-19 23:19:48 UTC

Updated at

2021-06-30 00:01:49 UTC

NP-MRD ID

NP0032559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

macrodaphniphyllamine

Provided By

JEOL Database JEOL Logo

Description

macrodaphniphyllamine is found in Daphniphyllum macropodum Miq. and Daphniphyllum yunnanense. macrodaphniphyllamine was first documented in 2006 (Di, Y. -T., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101193D          

 61 66  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202101193D          

 61 66  0  0  0  0            999 V2000
    4.6101    2.0041    4.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5225    2.6593    3.6260 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4695    1.3153    2.9112 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.3823    3.9623   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    2.1564   -2.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6813    1.9402   -1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -0.5500   -1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7069   -0.9420    0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2891   -2.6742    0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6726   -3.6511   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3910   -3.2632   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4866   -2.0012   -2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451    0.4158   -2.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0338   -0.0881   -1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695    2.9334   -0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    2.6058   -1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906    1.6055   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416   -0.1703    1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5385    3.3643    3.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    4.5485    2.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392    2.5633    4.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862    3.1665    3.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2976    0.6838    3.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  1  0  0  0
  8  9  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 24  1  0  0  0  0
 24  7  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28  8  1  0  0  0  0
 10 11  1  0  0  0  0
  5  3  1  0  0  0  0
 12 11  1  0  0  0  0
 22 23  1  1  0  0  0
 19 20  1  0  0  0  0
 12 39  1  6  0  0  0
 20 22  1  0  0  0  0
 18 16  1  0  0  0  0
 24 18  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
  7  8  1  0  0  0  0
 20 21  1  0  0  0  0
  9 10  1  0  0  0  0
 24 25  1  1  0  0  0
  7 22  1  0  0  0  0
  3  2  1  0  0  0  0
 22 12  1  0  0  0  0
  2  1  1  0  0  0  0
 28  5  1  0  0  0  0
  3  4  2  0  0  0  0
  5  6  1  0  0  0  0
 28 61  1  1  0  0  0
 10 35  1  0  0  0  0
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  5 32  1  1  0  0  0
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  6 34  1  0  0  0  0
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 15 42  1  0  0  0  0
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 25 56  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])[C@]2([H])[C@]([H])(C([H])([H])[H])C([H])([H])N3C([H])([H])[C@@]4([H])C([H])([H])C([H])([H])C5=C6[C@]([H])(C([H])([H])C5([H])[H])[C@]([H])(C(=O)OC([H])([H])[H])C([H])([H])[C@]6([C@]23O[H])[C@@]14C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H33NO4/c1-12-10-24-11-14-6-4-13-5-7-15-16(20(26)28-3)9-22(19(13)15)21(14,2)18(25)8-17(12)23(22,24)27/h12,14-18,25,27H,4-11H2,1-3H3/t12-,14-,15-,16-,17-,18+,21-,22-,23-/m1/s1

> <INCHI_KEY>
VSUPHZOFQVOSCQ-FYNJOORZSA-N

> <FORMULA>
C23H33NO4

> <MOLECULAR_WEIGHT>
387.52

> <EXACT_MASS>
387.240958547

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
42.403886670807424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,3R,4R,10S,14S,15R,17S,18S,19R)-17,19-dihydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icos-7(20)-ene-3-carboxylate

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.655473600666666

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.666035066393352

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.607911584171923

> <JCHEM_PKA_STRONGEST_BASIC>
10.415065102004752

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
105.51989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,3R,4R,10S,14S,15R,17S,18S,19R)-17,19-dihydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icos-7(20)-ene-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 66  0  0  0  0  0  0  0  0999 V2000
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    2.2860   -0.6588   -1.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9695    2.1358   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.2910    0.2702 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.5225    2.6593    3.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4695    1.3153    2.9112 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.8247    1.9663    5.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7732   -0.3378    3.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4481   -0.1026    0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530   -1.1783    1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2427    4.6995    0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360    4.0132   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823    3.9623   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6726   -3.6511   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3566   -2.2228   -3.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0472   -2.2493   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4866   -2.0012   -2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451    0.4158   -2.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0338   -0.0881   -1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695    2.9334   -0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5385    3.3643    3.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    4.5485    2.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392    2.5633    4.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862    3.1665    3.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2976    0.6838    3.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  1
  8  9  2  0
 12 13  1  0
 13 14  1  0
 14 24  1  0
 24  7  1  0
  9 26  1  0
 26 27  1  0
 27 28  1  0
 28  8  1  0
 10 11  1  0
  5  3  1  0
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 22 23  1  1
 19 20  1  0
 12 39  1  6
 20 22  1  0
 18 16  1  0
 24 18  1  0
 16 17  1  0
 18 19  1  0
 16 15  1  0
 15 14  1  0
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 20 21  1  0
  9 10  1  0
 24 25  1  1
  7 22  1  0
  3  2  1  0
 22 12  1  0
  2  1  1  0
 28  5  1  0
  3  4  2  0
  5  6  1  0
 28 61  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 40  1  0
 13 41  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  6
 18 48  1  1
  5 32  1  1
  6 33  1  0
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 26 57  1  0
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 21 52  1  0
 25 56  1  0
  1 29  1  0
  1 30  1  0
  1 31  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       4.610   2.004   4.322  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.394   1.292   4.089  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.010   1.262   2.777  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.629   1.788   1.863  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.709   0.492   2.651  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.502  -0.117   1.242  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.345   0.648   0.496  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.016   1.703   1.538  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.585   2.898   1.545  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.269   3.624   0.444  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.697   3.446  -0.957  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.507   2.006  -1.490  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.845   1.230  -1.446  0.00  0.00           C+0
HETATM   14  N   UNK     0      -2.092   0.352  -0.293  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.982  -0.770  -0.692  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.089  -2.015  -0.848  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.387  -2.829  -2.098  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.651  -1.474  -0.685  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.025  -1.093  -2.011  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.076   0.011  -1.893  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.286  -0.659  -1.540  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.729   1.204  -0.913  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.970   2.136  -0.862  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.894  -0.291   0.270  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.289  -0.828   1.534  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.563   3.488   2.932  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.523   2.659   3.626  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.470   1.315   2.911  0.00  0.00           C+0
HETATM   29  H   UNK     0       5.440   1.533   3.785  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.825   1.966   5.393  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.502   3.053   4.027  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.773  -0.338   3.368  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.448  -0.103   0.700  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.253  -1.178   1.359  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.331   3.350   0.456  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.243   4.699   0.663  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.236   4.013  -1.042  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.382   3.962  -1.645  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.286   2.156  -2.559  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.935   0.687  -2.393  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.681   1.940  -1.497  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.572  -0.550  -1.590  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.707  -0.942   0.113  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.289  -2.674   0.010  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.673  -3.651  -2.205  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.391  -3.263  -2.035  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.357  -2.223  -3.008  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.047  -2.249  -0.196  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.703  -0.796  -2.768  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.487  -2.001  -2.424  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.245   0.416  -2.899  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.034  -0.088  -1.788  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.869   2.933  -0.121  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.135   2.606  -1.839  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.891   1.605  -0.611  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.942  -0.170   1.834  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.539   3.364   3.415  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.294   4.548   2.930  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.339   2.563   4.701  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.486   3.167   3.503  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.298   0.684   3.378  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    3   28    6   32                                             
CONECT    6    7    5   33   34                                             
CONECT    7    6   24    8   22                                             
CONECT    8    9   28    7                                                  
CONECT    9    8   26   10                                                  
CONECT   10   11    9   35   36                                             
CONECT   11   10   12   37   38                                             
CONECT   12   13   11   39   22                                             
CONECT   13   12   14   40   41                                             
CONECT   14   13   24   15                                                  
CONECT   15   16   14   42   43                                             
CONECT   16   18   17   15   44                                             
CONECT   17   16   45   46   47                                             
CONECT   18   16   24   19   48                                             
CONECT   19   20   18   49   50                                             
CONECT   20   19   22   21   51                                             
CONECT   21   20   52                                                       
CONECT   22   23   20    7   12                                             
CONECT   23   22   53   54   55                                             
CONECT   24   14    7   18   25                                             
CONECT   25   24   56                                                       
CONECT   26    9   27   57   58                                             
CONECT   27   26   28   59   60                                             
CONECT   28   27    8    5   61                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   13                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   27                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  132    0
END

RDKit          3D

61 66  0  0  0  0  0  0  0  0999 V2000
    4.6101    2.0041    4.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3945    1.2922    4.0888 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0104    1.2624    2.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289    1.7883    1.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7091    0.4915    2.6505 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5023   -0.1170    1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3448    0.6481    0.4955 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0163    1.7033    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5846    2.8985    1.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693    3.6238    0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6969    3.4455   -0.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5066    2.0065   -1.4902 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8451    1.2301   -1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920    0.3517   -0.2930 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9817   -0.7695   -0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894   -2.0152   -0.8477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3873   -2.8289   -2.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507   -1.4739   -0.6848 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0247   -1.0934   -2.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0757    0.0113   -1.8927 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2860   -0.6588   -1.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289    1.2039   -0.9125 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9695    2.1358   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.2910    0.2702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2887   -0.8282    1.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633    3.4880    2.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5225    2.6593    3.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4695    1.3153    2.9112 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4396    1.5327    3.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    1.9663    5.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5022    3.0527    4.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732   -0.3378    3.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4481   -0.1026    0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530   -1.1783    1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3312    3.3501    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2427    4.6995    0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360    4.0132   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823    3.9623   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    2.1564   -2.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9345    0.6868   -2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813    1.9402   -1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -0.5500   -1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7069   -0.9420    0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2891   -2.6742    0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6726   -3.6511   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3910   -3.2632   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566   -2.2228   -3.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0472   -2.2493   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -0.7962   -2.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4866   -2.0012   -2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451    0.4158   -2.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0338   -0.0881   -1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695    2.9334   -0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    2.6058   -1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906    1.6055   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416   -0.1703    1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5385    3.3643    3.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    4.5485    2.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392    2.5633    4.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862    3.1665    3.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2976    0.6838    3.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  1
  8  9  2  0
 12 13  1  0
 13 14  1  0
 14 24  1  0
 24  7  1  0
  9 26  1  0
 26 27  1  0
 27 28  1  0
 28  8  1  0
 10 11  1  0
  5  3  1  0
 12 11  1  0
 22 23  1  1
 19 20  1  0
 12 39  1  6
 20 22  1  0
 18 16  1  0
 24 18  1  0
 16 17  1  0
 18 19  1  0
 16 15  1  0
 15 14  1  0
  7  8  1  0
 20 21  1  0
  9 10  1  0
 24 25  1  1
  7 22  1  0
  3  2  1  0
 22 12  1  0
  2  1  1  0
 28  5  1  0
  3  4  2  0
  5  6  1  0
 28 61  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 40  1  0
 13 41  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  6
 18 48  1  1
  5 32  1  1
  6 33  1  0
  6 34  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 16 44  1  1
 17 45  1  0
 17 46  1  0
 17 47  1  0
 15 42  1  0
 15 43  1  0
 21 52  1  0
 25 56  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₃NO₄

Average Mass

387.5200 Da

Monoisotopic Mass

387.24096 Da

IUPAC Name

methyl (1R,3R,4R,10S,14S,15R,17S,18S,19R)-17,19-dihydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icos-7(20)-ene-3-carboxylate

Traditional Name

methyl (1R,3R,4R,10S,14S,15R,17S,18S,19R)-17,19-dihydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icos-7(20)-ene-3-carboxylate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])[C@]2([H])[C@]([H])(C([H])([H])[H])C([H])([H])N3C([H])([H])[C@@]4([H])C([H])([H])C([H])([H])C5=C6[C@]([H])(C([H])([H])C5([H])[H])[C@]([H])(C(=O)OC([H])([H])[H])C([H])([H])[C@]6([C@]23O[H])[C@@]14C([H])([H])[H]

InChI Identifier

InChI=1S/C23H33NO4/c1-12-10-24-11-14-6-4-13-5-7-15-16(20(26)28-3)9-22(19(13)15)21(14,2)18(25)8-17(12)23(22,24)27/h12,14-18,25,27H,4-11H2,1-3H3/t12-,14-,15-,16-,17-,18+,21-,22-,23-/m1/s1

InChI Key

VSUPHZOFQVOSCQ-FYNJOORZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Daphniphyllum macropodum	Plant	KNApSAcK
Daphniphyllum yunnanense	JEOL database	Di, Y. -T., et al, J. Nat. Prod. 69, 1745 (2006)

Chemical Taxonomy

Classification

Not classified

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	1.85	ALOGPS
logP	1.66	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.61	ChemAxon
pKa (Strongest Basic)	10.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.52 m³·mol⁻¹	ChemAxon
Polarizability	42.4 Å³	ChemAxon
Number of Rings	6	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

Not Available

References

General References

Di, Y. -T., et al. (2006). Di, Y. -T., et al, J. Nat. Prod. 69, 1745 (2006) . J. Nat. Prod..

Showing NP-Card for macrodaphniphyllamine (NP0032559)

MOL for NP0032559 (macrodaphniphyllamine)

3D MOL for NP0032559 (macrodaphniphyllamine)

3D SDF for NP0032559 (macrodaphniphyllamine)

3D-SDF for NP0032559 (macrodaphniphyllamine)

PDB for NP0032559 (macrodaphniphyllamine)

3D PDB for NP0032559 (macrodaphniphyllamine)

SMILES for NP0032559 (macrodaphniphyllamine)

INCHI for NP0032559 (macrodaphniphyllamine)

Structure for NP0032559 (macrodaphniphyllamine)

3D Structure for NP0032559 (macrodaphniphyllamine)