NP-MRD: Showing NP-Card for (1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate (NP0329227)

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Record Information

Version

2.0

Created at

2022-09-12 13:25:48 UTC

Updated at

2022-09-12 13:25:48 UTC

NP-MRD ID

NP0329227

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate

Description

(1R,2R,3R,4S,5S,7R,8S,9R,11R,12S,14R,17S,18R)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]Octadecan-5-yl benzoate belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. (1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate is found in Delphinium barbeyi. Based on a literature review very few articles have been published on (1R,2R,3R,4S,5S,7R,8S,9R,11R,12S,14R,17S,18R)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]Octadecan-5-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122215252D          

 42 48  0  0  1  0            999 V2000
   -0.8981   -0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970    0.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3474    0.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3123    0.8286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6334    1.7340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1221    2.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057    2.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2056    2.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    1.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5628    1.8336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0604    1.1564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9070    1.2881    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7158    2.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6918    1.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8638    2.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2302    0.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8563   -0.2474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2169   -0.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0398   -1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9465    2.2707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5765    3.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
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  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
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 12 13  1  1  0  0  0
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 21 26  1  0  0  0  0
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 27 32  1  0  0  0  0
 32 11  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  4 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  2  0  0  0  0
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  2 37  1  0  0  0  0
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 32 40  1  0  0  0  0
 33 41  1  1  0  0  0
 10 41  1  6  0  0  0
 41 42  1  0  0  0  0
M  END

     RDKit          3D

 77 83  0  0  0  0  0  0  0  0999 V2000
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   -2.9882   -0.4072   -0.9028 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.4105   -0.6703   -1.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4271    0.1525    1.3742 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122215252D          

 42 48  0  0  1  0            999 V2000
   -0.8981   -0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970    0.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3123    0.8286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6334    1.7340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1221    2.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057    2.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8563   -0.2474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2169   -0.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0398   -1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5021   -0.3649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4003   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2232   -1.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5838   -2.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1215   -3.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2986   -3.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9380   -2.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304   -0.0739    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6177   -0.7882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0299   -1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8549   -1.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6172   -2.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    0.5760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.3025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9644    1.4067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7994    0.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3684   -0.1290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6377   -0.3782    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4097   -0.7108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7166   -1.4766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7462    0.0811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9465    2.2707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5765    3.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 11  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  4 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  2  0  0  0  0
 37 35  1  6  0  0  0
  2 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40  4  1  6  0  0  0
 32 40  1  0  0  0  0
 33 41  1  1  0  0  0
 10 41  1  6  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329227

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@@H]2[C@H]3[C@@]4([C@H]1[C@H]1C(=O)[C@H]5[C@H](O)[C@@H]4[C@@]1(CC5=C)[C@@H]2OC(C)=O)[C@H](OC(C)=O)[C@H](C[C@@]3(C)C=O)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H35NO9/c1-14-11-31-20-22(37)19(14)23(38)25(31)32-24(21(33(5)26(20)32)28(31)41-16(3)36)30(4,13-34)12-18(27(32)40-15(2)35)42-29(39)17-9-7-6-8-10-17/h6-10,13,18-21,23-28,38H,1,11-12H2,2-5H3/t18-,19-,20+,21+,23-,24+,25+,26+,27+,28+,30-,31-,32+/m0/s1

> <INCHI_KEY>
REQUJTKBFQSUNF-WIAAIORRSA-N

> <FORMULA>
C32H35NO9

> <MOLECULAR_WEIGHT>
577.63

> <EXACT_MASS>
577.231181711

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.771445543626186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,4S,5S,7R,8S,9R,11R,12S,14R,17S,18R)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1^{2,14}.0^{1,12}.0^{3,8}.0^{3,11}]octadecan-5-yl benzoate

> <JCHEM_LOGP>
1.2042933896666672

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.157078528326153

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.870933961296132

> <JCHEM_PKA_STRONGEST_BASIC>
8.088071520801707

> <JCHEM_POLAR_SURFACE_AREA>
136.51000000000002

> <JCHEM_REFRACTIVITY>
145.3443

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,4S,5S,7R,8S,9R,11R,12S,14R,17S,18R)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1^{2,14}.0^{1,12}.0^{3,8}.0^{3,11}]octadecan-5-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.676  -0.238   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.181   0.131   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.649   1.516   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.450   1.547   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.049   3.237   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.095   4.445   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.571   4.223   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.384   5.432   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.001   2.792   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.784   3.423   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.713   2.159   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.293   2.404   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.936   3.902   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.758   2.879   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.079   4.386   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.896   0.950   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.198  -0.462   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.871  -1.847   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.408  -1.957   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.271  -0.681   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.081  -3.342   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.617  -3.451   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.290  -4.837   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.427  -6.112   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.891  -6.002   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.218  -4.617   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.657  -0.138   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.886  -1.471   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.656  -2.805   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.196  -2.806   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.885  -4.139   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.571   1.075   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.590   2.431   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.800   2.626   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.492   0.874   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.554  -0.241   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.190  -0.706   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.632  -1.327   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.204  -2.756   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.260   0.151   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0       3.633   4.239   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0       2.943   5.615   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   34   40                                             
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   41                                                  
CONECT   11   10   12   32                                                  
CONECT   12   11   13   14   16                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   17   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   11   33   40                                             
CONECT   33   32   34   41                                                  
CONECT   34   33    4   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    2   38                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38    4   32                                                  
CONECT   41   33   10   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,3R,4S,5S,7R,8S,9R,11R,12S,14R,17S,18R)-4,17-Bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1,.0,.0,.0,]octadecan-5-yl benzoic acid	Generator

Chemical Formula

C₃₂H₃₅NO₉

Average Mass

577.6300 Da

Monoisotopic Mass

577.23118 Da

IUPAC Name

(1R,2R,3R,4S,5S,7R,8S,9R,11R,12S,14R,17S,18R)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1^{2,14}.0^{1,12}.0^{3,8}.0^{3,11}]octadecan-5-yl benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CN1[C@@H]2[C@H]3[C@@]4([C@H]1[C@H]1C(=O)[C@H]5[C@H](O)[C@@H]4[C@@]1(CC5=C)[C@@H]2OC(C)=O)[C@H](OC(C)=O)[C@H](C[C@@]3(C)C=O)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C32H35NO9/c1-14-11-31-20-22(37)19(14)23(38)25(31)32-24(21(33(5)26(20)32)28(31)41-16(3)36)30(4,13-34)12-18(27(32)40-15(2)35)42-29(39)17-9-7-6-8-10-17/h6-10,13,18-21,23-28,38H,1,11-12H2,2-5H3/t18-,19-,20+,21+,23-,24+,25+,26+,27+,28+,30-,31-,32+/m0/s1

InChI Key

REQUJTKBFQSUNF-WIAAIORRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Delphinium barbeyi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Azaphilone
Azaspirodecane
Benzoate ester
Benzoic acid or derivatives
Isoindoline
Isoindole or derivatives
Tricarboxylic acid or derivatives
Alkaloid or derivatives
Benzoyl
Azepane
Benzenoid
Monocyclic benzene moiety
N-alkylpyrrolidine
Piperidine
Pyrrolidine
Cyclic alcohol
Amino acid or derivatives
Tertiary aliphatic amine
Ketone
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organopnictogen compound
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aldehyde
Amine
Organonitrogen compound
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	1.2	ChemAxon
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	8.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	136.51 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	145.34 m³·mol⁻¹	ChemAxon
Polarizability	55.77 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163028596

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate (NP0329227)

MOL for NP0329227 ((1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate)

3D MOL for NP0329227 ((1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate)

3D SDF for NP0329227 ((1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate)

3D-SDF for NP0329227 ((1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate)

PDB for NP0329227 ((1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate)

3D PDB for NP0329227 ((1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate)

SMILES for NP0329227 ((1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate)

INCHI for NP0329227 ((1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate)

Structure for NP0329227 ((1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate)

3D Structure for NP0329227 ((1r,2r,3r,4s,5s,7r,8s,9r,11r,12s,14r,17s,18r)-4,17-bis(acetyloxy)-7-formyl-18-hydroxy-7,10-dimethyl-15-methylidene-13-oxo-10-azahexacyclo[7.7.1.1²,¹⁴.0¹,¹².0³,⁸.0³,¹¹]octadecan-5-yl benzoate)