NP-MRD: Showing NP-Card for 17-hydroxydaphnigraciline (NP0034792)

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Record Information

Version

2.0

Created at

2021-06-20 18:25:12 UTC

Updated at

2021-06-30 00:05:24 UTC

NP-MRD ID

NP0034792

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-hydroxydaphnigraciline

Provided By

JEOL Database JEOL Logo

Description

17-hydroxydaphnigraciline is found in Daphniphyllum subverticillatum. 17-hydroxydaphnigraciline was first documented in 2009 ( Zhang, C. -R., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120253D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202120253D          

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    1.1520    2.4923   -2.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5832   -0.3115   -0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875   -1.9260   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0511    0.8493    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696    0.3263    1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2745    2.1471    0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771    2.1431    0.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783   -0.1728   -3.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071    1.6332   -4.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6146    1.3503   -4.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0084   -1.7408   -4.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7295   -2.6072   -2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8516   -3.3639   -2.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7348   -2.6658   -1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6306   -3.1886   -0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7622   -1.5557    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9506   -0.8787    1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825   -2.2883    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 10  1  0  0  0  0
  7  6  1  1  0  0  0
 13 17  1  0  0  0  0
 17 16  1  0  0  0  0
 16 15  1  0  0  0  0
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  6  5  1  0  0  0  0
 29 27  1  0  0  0  0
 13 12  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 11 12  1  0  0  0  0
  3  4  1  6  0  0  0
 25 14  1  0  0  0  0
  3  2  1  0  0  0  0
  5  3  1  0  0  0  0
  2  1  1  0  0  0  0
  3  9  1  0  0  0  0
 27 28  1  0  0  0  0
  9  8  1  0  0  0  0
 10 42  1  6  0  0  0
  8  7  1  0  0  0  0
 15 47  1  1  0  0  0
 14 15  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 22  1  0  0  0  0
 24 25  1  0  0  0  0
 20 21  2  0  0  0  0
 14 13  2  0  0  0  0
 22 23  1  0  0  0  0
  7 25  1  0  0  0  0
  6 38  1  0  0  0  0
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  5 36  1  0  0  0  0
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 23 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034792

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C2=C3[C@]([H])(C1([H])[H])[C@]([H])(C(=O)OC([H])([H])[H])C([H])([H])[C@]31C([H])([H])N(C([H])([H])[H])C([H])([H])[C@@]([H])(C([H])([H])C2([H])[H])[C@]11C([H])([H])O[C@@](O[H])(C([H])([H])C([H])([H])[H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H35NO5/c1-4-23(27)8-7-21(13-29-23)14-5-6-15-18(25)9-16-17(20(26)28-3)10-22(21,19(15)16)12-24(2)11-14/h14,16-18,25,27H,4-13H2,1-3H3/t14-,16-,17-,18+,21+,22+,23+/m1/s1

> <INCHI_KEY>
JQSUAFILVQFOIV-IMFDLFKKSA-N

> <FORMULA>
C23H35NO5

> <MOLECULAR_WEIGHT>
405.535

> <EXACT_MASS>
405.251523231

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
44.87239932243555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1'S,3S,6S,9'S,11'R,12'R)-6-ethyl-6,9'-dihydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1^{1,5}.0^{11,14}]pentadecan]-8'(14')-ene-12'-carboxylate

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
0.8531256636666651

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.388063407061818

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.081176665911308

> <JCHEM_PKA_STRONGEST_BASIC>
9.959026853603522

> <JCHEM_POLAR_SURFACE_AREA>
79.22999999999999

> <JCHEM_REFRACTIVITY>
109.67139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'S,3S,6S,9'S,11'R,12'R)-6-ethyl-6,9'-dihydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1^{1,5}.0^{11,14}]pentadecan]-8'(14')-ene-12'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    4.1882   -2.2482    2.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8034   -2.8849    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4272    0.4441    1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3868    1.0490   -1.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282   -0.1705   -1.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5426    1.2738   -3.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012    2.0701   -2.5280 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1520    2.4923   -2.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131   -1.4549   -3.9820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0544   -1.5226   -4.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6122   -2.9077   -5.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459   -2.3977   -2.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8177   -1.6065   -1.5203 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.7989   -2.3670    0.0985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2439   -2.5169    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8292   -4.5467    1.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883   -3.0039    2.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -3.8517   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9531   -3.7899    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5832   -0.3115   -0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875   -1.9260   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2745    2.1471    0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9783   -0.1728   -3.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071    1.6332   -4.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6146    1.3503   -4.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7295   -2.6072   -2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8516   -3.3639   -2.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9749   -0.9857   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9825   -2.2883    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 10  1  0
  7  6  1  1
 13 17  1  0
 17 16  1  0
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  6  5  1  0
 29 27  1  0
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  3  4  1  6
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  3  2  1  0
  5  3  1  0
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  3  9  1  0
 27 28  1  0
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 14 15  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 19 24  1  0
 20 22  1  0
 24 25  1  0
 20 21  2  0
 14 13  2  0
 22 23  1  0
  7 25  1  0
  6 38  1  0
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 18 51  1  0
 23 53  1  0
 23 54  1  0
 23 55  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       4.188  -2.248   2.974  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.803  -2.885   2.902  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.165  -2.862   1.500  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.957  -3.623   0.600  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.764  -3.475   1.567  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.012  -3.289   0.249  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.065  -1.787  -0.172  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.434  -1.357  -0.213  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.089  -1.517   1.051  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.000  -0.872   0.730  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.427   0.444   1.232  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.395   1.501   0.049  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.387   1.049  -1.420  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.528  -0.171  -1.989  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.123  -0.131  -3.430  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.543   1.274  -3.813  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.201   2.070  -2.528  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.152   2.492  -2.572  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.613  -1.455  -3.982  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.054  -1.523  -4.449  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.903  -0.656  -4.304  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.274  -2.724  -5.059  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.612  -2.908  -5.522  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.346  -2.398  -2.770  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.818  -1.607  -1.520  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.403  -1.891  -1.271  0.00  0.00           C+0
HETATM   27  N   UNK     0      -2.799  -2.367   0.099  0.00  0.00           N+0
HETATM   28  C   UNK     0      -4.244  -2.517   0.222  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.225  -1.606   1.249  0.00  0.00           C+0
HETATM   30  H   UNK     0       4.917  -2.804   2.376  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.544  -2.247   4.009  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.170  -1.211   2.625  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.886  -3.920   3.255  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.157  -2.344   3.605  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.823  -3.185   0.584  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.829  -4.547   1.788  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.188  -3.004   2.371  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.542  -3.852  -0.533  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.953  -3.790   0.330  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.583  -0.312  -0.481  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.988  -1.926  -0.970  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.654  -0.306   0.061  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.051   0.849   2.039  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.570   0.326   1.664  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.274   2.147   0.171  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.477   2.143   0.224  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.978  -0.173  -3.465  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.007   1.633  -4.688  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.615   1.350  -4.017  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.856   2.940  -2.420  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.367   2.857  -1.698  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.008  -1.741  -4.840  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.678  -3.896  -5.986  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.864  -2.154  -6.275  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.316  -2.871  -4.685  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.730  -2.607  -2.718  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.852  -3.364  -2.869  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.735  -2.666  -1.972  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.975  -0.986  -1.518  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.631  -3.189  -0.553  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.504  -2.965   1.187  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.762  -1.556   0.135  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.951  -0.879   1.638  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.982  -2.288   2.069  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1   33   34                                             
CONECT    3    4    2    5    9                                             
CONECT    4    3   35                                                       
CONECT    5    6    3   36   37                                             
CONECT    6    7    5   38   39                                             
CONECT    7   10    6    8   25                                             
CONECT    8    9    7   40   41                                             
CONECT    9    3    8                                                       
CONECT   10    7   11   29   42                                             
CONECT   11   10   12   43   44                                             
CONECT   12   13   11   45   46                                             
CONECT   13   17   12   14                                                  
CONECT   14   25   15   13                                                  
CONECT   15   16   47   14   19                                             
CONECT   16   17   15   48   49                                             
CONECT   17   13   16   18   50                                             
CONECT   18   17   51                                                       
CONECT   19   15   20   24   52                                             
CONECT   20   19   22   21                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   53   54   55                                             
CONECT   24   19   25   56   57                                             
CONECT   25   26   14   24    7                                             
CONECT   26   25   27   58   59                                             
CONECT   27   29   26   28                                                  
CONECT   28   27   60   61   62                                             
CONECT   29   10   27   63   64                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    6                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   28                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   29                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  136    0
END

RDKit          3D

64 68  0  0  0  0  0  0  0  0999 V2000
    4.1882   -2.2482    2.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8034   -2.8849    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649   -2.8618    1.5003 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9573   -3.6225    0.5999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642   -3.4746    1.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0123   -3.2894    0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0651   -1.7872   -0.1716 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4343   -1.3572   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893   -1.5170    1.0513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995   -0.8719    0.7296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4272    0.4441    1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3946    1.5009    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3868    1.0490   -1.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282   -0.1705   -1.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231   -0.1310   -3.4296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5426    1.2738   -3.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012    2.0701   -2.5280 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1520    2.4923   -2.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131   -1.4549   -3.9820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0544   -1.5226   -4.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9030   -0.6561   -4.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738   -2.7245   -5.0588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6122   -2.9077   -5.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459   -2.3977   -2.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8177   -1.6065   -1.5203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4026   -1.8908   -1.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7989   -2.3670    0.0985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2439   -2.5169    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2249   -1.6062    1.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9171   -2.8036    2.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441   -2.2473    4.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1704   -1.2111    2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860   -3.9204    3.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1573   -2.3435    3.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8232   -3.1848    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -4.5467    1.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883   -3.0039    2.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -3.8517   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9531   -3.7899    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5832   -0.3115   -0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875   -1.9260   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6537   -0.3059    0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0511    0.8493    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696    0.3263    1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2745    2.1471    0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771    2.1431    0.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783   -0.1728   -3.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071    1.6332   -4.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6146    1.3503   -4.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8564    2.9398   -2.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3669    2.8573   -1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0084   -1.7408   -4.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6778   -3.8958   -5.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8636   -2.1541   -6.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3158   -2.8708   -4.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7295   -2.6072   -2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8516   -3.3639   -2.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7348   -2.6658   -1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9749   -0.9857   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6306   -3.1886   -0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5036   -2.9651    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7622   -1.5557    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9506   -0.8787    1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825   -2.2883    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 10  1  0
  7  6  1  1
 13 17  1  0
 17 16  1  0
 16 15  1  0
 10 11  1  0
 10 29  1  0
  6  5  1  0
 29 27  1  0
 13 12  1  0
 25 26  1  1
 26 27  1  0
 11 12  1  0
  3  4  1  6
 25 14  1  0
  3  2  1  0
  5  3  1  0
  2  1  1  0
  3  9  1  0
 27 28  1  0
  9  8  1  0
 10 42  1  6
  8  7  1  0
 15 47  1  1
 14 15  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 19 24  1  0
 20 22  1  0
 24 25  1  0
 20 21  2  0
 14 13  2  0
 22 23  1  0
  7 25  1  0
  6 38  1  0
  6 39  1  0
  5 36  1  0
  5 37  1  0
  8 40  1  0
  8 41  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 19 52  1  6
 24 56  1  0
 24 57  1  0
 17 50  1  1
 16 48  1  0
 16 49  1  0
 29 63  1  0
 29 64  1  0
 26 58  1  0
 26 59  1  0
  4 35  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
 18 51  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₅NO₅

Average Mass

405.5350 Da

Monoisotopic Mass

405.25152 Da

IUPAC Name

methyl (1'S,3S,6S,9'S,11'R,12'R)-6-ethyl-6,9'-dihydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1^{1,5}.0^{11,14}]pentadecan]-8'(14')-ene-12'-carboxylate

Traditional Name

methyl (1'S,3S,6S,9'S,11'R,12'R)-6-ethyl-6,9'-dihydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1^{1,5}.0^{11,14}]pentadecan]-8'(14')-ene-12'-carboxylate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C2=C3[C@]([H])(C1([H])[H])[C@]([H])(C(=O)OC([H])([H])[H])C([H])([H])[C@]31C([H])([H])N(C([H])([H])[H])C([H])([H])[C@@]([H])(C([H])([H])C2([H])[H])[C@]11C([H])([H])O[C@@](O[H])(C([H])([H])C([H])([H])[H])C([H])([H])C1([H])[H]

InChI Identifier

InChI=1S/C23H35NO5/c1-4-23(27)8-7-21(13-29-23)14-5-6-15-18(25)9-16-17(20(26)28-3)10-22(21,19(15)16)12-24(2)11-14/h14,16-18,25,27H,4-13H2,1-3H3/t14-,16-,17-,18+,21+,22+,23+/m1/s1

InChI Key

JQSUAFILVQFOIV-IMFDLFKKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Daphniphyllum subverticillatum	JEOL database	Zhang, C. -R., et al, J. Nat. Prod. 72, 1669 (2009)

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	1.36	ALOGPS
logP	0.85	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	9.96	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	3	ChemAxon
Refractivity	109.67 m³·mol⁻¹	ChemAxon
Polarizability	44.87 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

Not Available

References

General References

Zhang, C. -R., et al. (2009). Zhang, C. -R., et al, J. Nat. Prod. 72, 1669 (2009). J. Nat. Prod..

Showing NP-Card for 17-hydroxydaphnigraciline (NP0034792)

MOL for NP0034792 (17-hydroxydaphnigraciline)

3D MOL for NP0034792 (17-hydroxydaphnigraciline)

3D SDF for NP0034792 (17-hydroxydaphnigraciline)

3D-SDF for NP0034792 (17-hydroxydaphnigraciline)

PDB for NP0034792 (17-hydroxydaphnigraciline)

3D PDB for NP0034792 (17-hydroxydaphnigraciline)

SMILES for NP0034792 (17-hydroxydaphnigraciline)

INCHI for NP0034792 (17-hydroxydaphnigraciline)

Structure for NP0034792 (17-hydroxydaphnigraciline)

3D Structure for NP0034792 (17-hydroxydaphnigraciline)