NP-MRD: Showing NP-Card for azitine (NP0029223)

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Record Information

Version

2.0

Created at

2021-06-19 20:54:26 UTC

Updated at

2021-06-29 23:56:27 UTC

NP-MRD ID

NP0029223

Secondary Accession Numbers

None

Natural Product Identification

Common Name

azitine

Provided By

JEOL Database JEOL Logo

Description

Azitine is also known as isoazitine. azitine is found in Consolida hellespontica, Consolida raveyi, Consolida raveyi Boiss Schrod, Delphinium stapeliosum and Delphinium staphisagria. azitine was first documented in 2004 (PMID: 15387663). Based on a literature review a small amount of articles have been published on Azitine (PMID: 16391494) (PMID: 15664483) (PMID: 29611891).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122543D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192122543D          

 51 55  0  0  0  0            999 V2000
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    3.2655    0.3095    1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713    2.4761    0.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8235    2.6768    0.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.5503   -2.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0611    0.0962   -0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  1  0  0  0
 19  6  1  0  0  0  0
 14  9  1  0  0  0  0
 10 18  1  0  0  0  0
  2 21  1  0  0  0  0
 10  9  1  0  0  0  0
 19 20  1  0  0  0  0
  6 21  1  0  0  0  0
 14 13  1  0  0  0  0
  2  3  1  0  0  0  0
 14 15  1  1  0  0  0
  3 20  1  0  0  0  0
  2  1  2  3  0  0  0
 17 18  1  0  0  0  0
 21 22  1  0  0  0  0
 10 11  1  6  0  0  0
  3  4  1  0  0  0  0
 10 19  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  1  0  0  0  0
  9  8  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8  7  1  0  0  0  0
 17 16  1  0  0  0  0
 14 16  1  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
  9 34  1  1  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
 19 47  1  1  0  0  0
  3 25  1  6  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 11 35  1  0  0  0  0
  7 30  1  0  0  0  0
  7 31  1  0  0  0  0
 21 50  1  6  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
 22 51  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029223

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]11C([H])([H])C([H])([H])[C@@]3([H])[C@]4(C([H])=NC([H])([H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])C4([H])[H])[C@]1([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H29NO/c1-13-14-4-8-19(17(13)22)9-5-15-18(2)6-3-7-20(15,12-21-11-18)16(19)10-14/h12,14-17,22H,1,3-11H2,2H3/t14-,15+,16+,17+,18-,19-,20-/m0/s1

> <INCHI_KEY>
UUTPNBAAXAQHKM-YQXKYMSPSA-N

> <FORMULA>
C20H29NO

> <MOLECULAR_WEIGHT>
299.458

> <EXACT_MASS>
299.224914558

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.86550522414595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4S,6R,7S,10R,11R)-11-methyl-5-methylidene-13-azapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadec-13-en-6-ol

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.048454396

> <ALOGPS_LOGS>
-5.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.774630580562604

> <JCHEM_PKA_STRONGEST_BASIC>
3.9512462226258616

> <JCHEM_POLAR_SURFACE_AREA>
32.59

> <JCHEM_REFRACTIVITY>
88.2669

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.92e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,6R,7S,10R,11R)-11-methyl-5-methylidene-13-azapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadec-13-en-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
    5.6408    2.0784   -2.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    1.5111   -1.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2210    2.2912   -1.4128 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1784    1.7211   -2.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9892    0.2133   -2.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8484   -0.2630   -0.9489 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6595   -1.7627   -0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2999   -2.0993   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367   -1.3185    1.2321 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1493    0.2134    1.0317 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0777    0.6932    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2288    0.1204    0.2481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4703   -1.1470    0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3398   -1.6248    1.8764 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5261   -3.1354    2.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4192   -0.9225    3.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578    0.5768    3.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921    0.9214    2.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    0.5728    0.3287 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7270    2.0812    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3423    0.0307   -1.3347 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2097   -0.3471   -0.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5395    1.4958   -2.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6967    3.1433   -2.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637    3.3611   -1.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2213    2.2407   -2.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876    1.8947   -3.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882   -0.3298   -3.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265   -0.0074   -2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -2.3341   -1.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318   -2.1194    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5145   -1.9180   -0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2888   -3.1762    0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195   -1.6285    1.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020    1.6551   -0.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4064   -1.0569    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -1.8999    0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533   -3.3255    2.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3037   -3.5391    2.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5874   -3.7110    1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -1.3782    3.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993   -1.0991    3.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293    1.0949    2.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466    0.9556    4.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739    0.6378    3.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1314    2.0113    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2655    0.3095    1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713    2.4761    0.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8235    2.6768    0.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.5503   -2.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0611    0.0962   -0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  1
 19  6  1  0
 14  9  1  0
 10 18  1  0
  2 21  1  0
 10  9  1  0
 19 20  1  0
  6 21  1  0
 14 13  1  0
  2  3  1  0
 14 15  1  1
  3 20  1  0
  2  1  2  3
 17 18  1  0
 21 22  1  0
 10 11  1  6
  3  4  1  0
 10 19  1  0
  6  5  1  0
  5  4  1  0
  9  8  1  0
 11 12  2  0
 12 13  1  0
  8  7  1  0
 17 16  1  0
 14 16  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
  9 34  1  1
  8 32  1  0
  8 33  1  0
 19 47  1  1
  3 25  1  6
 20 48  1  0
 20 49  1  0
 11 35  1  0
  7 30  1  0
  7 31  1  0
 21 50  1  6
 13 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
  1 23  1  0
  1 24  1  0
 22 51  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
 16 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       5.641   2.078  -2.053  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.505   1.511  -1.616  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.221   2.291  -1.413  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.178   1.721  -2.388  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.989   0.213  -2.152  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.848  -0.263  -0.949  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.660  -1.763  -0.676  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.300  -2.099  -0.073  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.037  -1.319   1.232  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.149   0.213   1.032  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.078   0.693   0.271  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.229   0.120   0.248  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.470  -1.147   0.941  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.340  -1.625   1.876  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.526  -3.135   2.137  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.419  -0.923   3.260  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.158   0.577   3.222  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.092   0.921   2.414  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.501   0.573   0.329  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.727   2.081   0.031  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.342   0.031  -1.335  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.210  -0.347  -0.272  0.00  0.00           O+0
HETATM   23  H   UNK     0       6.540   1.496  -2.229  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.697   3.143  -2.260  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.364   3.361  -1.603  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.221   2.241  -2.261  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.488   1.895  -3.426  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.288  -0.330  -3.059  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.927  -0.007  -2.021  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.795  -2.334  -1.602  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.432  -2.119   0.018  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.515  -1.918  -0.813  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.289  -3.176   0.129  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.819  -1.629   1.941  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.002   1.655  -0.257  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.406  -1.057   1.505  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.662  -1.900   0.166  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.453  -3.325   2.691  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.304  -3.539   2.728  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.587  -3.711   1.208  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.320  -1.378   3.934  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.399  -1.099   3.721  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.029   1.095   2.805  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.047   0.956   4.245  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.974   0.638   3.004  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.131   2.011   2.301  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.265   0.310   1.077  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.471   2.476   0.735  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.823   2.677   0.191  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.621  -0.550  -2.223  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.061   0.096  -0.417  0.00  0.00           H+0
CONECT    1    2   23   24                                                  
CONECT    2   21    3    1                                                  
CONECT    3    2   20    4   25                                             
CONECT    4    3    5   26   27                                             
CONECT    5    6    4   28   29                                             
CONECT    6    7   19   21    5                                             
CONECT    7    6    8   30   31                                             
CONECT    8    9    7   32   33                                             
CONECT    9   14   10    8   34                                             
CONECT   10   18    9   11   19                                             
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   14   12   36   37                                             
CONECT   14    9   13   15   16                                             
CONECT   15   14   38   39   40                                             
CONECT   16   17   14   41   42                                             
CONECT   17   18   16   43   44                                             
CONECT   18   10   17   45   46                                             
CONECT   19    6   20   10   47                                             
CONECT   20   19    3   48   49                                             
CONECT   21    2    6   22   50                                             
CONECT   22   21   51                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    7                                                            
CONECT   31    7                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   11                                                            
CONECT   36   13                                                            
CONECT   37   13                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END

RDKit          3D

51 55  0  0  0  0  0  0  0  0999 V2000
    5.6408    2.0784   -2.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    1.5111   -1.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2210    2.2912   -1.4128 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1784    1.7211   -2.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9892    0.2133   -2.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8484   -0.2630   -0.9489 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6595   -1.7627   -0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2999   -2.0993   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367   -1.3185    1.2321 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1493    0.2134    1.0317 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0777    0.6932    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2288    0.1204    0.2481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4703   -1.1470    0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3398   -1.6248    1.8764 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5261   -3.1354    2.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4192   -0.9225    3.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578    0.5768    3.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921    0.9214    2.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    0.5728    0.3287 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7270    2.0812    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3423    0.0307   -1.3347 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2097   -0.3471   -0.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5395    1.4958   -2.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6967    3.1433   -2.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637    3.3611   -1.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2213    2.2407   -2.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876    1.8947   -3.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882   -0.3298   -3.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265   -0.0074   -2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -2.3341   -1.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318   -2.1194    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5145   -1.9180   -0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2888   -3.1762    0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195   -1.6285    1.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020    1.6551   -0.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4064   -1.0569    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -1.8999    0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533   -3.3255    2.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3037   -3.5391    2.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5874   -3.7110    1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -1.3782    3.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993   -1.0991    3.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293    1.0949    2.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466    0.9556    4.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739    0.6378    3.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1314    2.0113    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2655    0.3095    1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713    2.4761    0.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8235    2.6768    0.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.5503   -2.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0611    0.0962   -0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  1
 19  6  1  0
 14  9  1  0
 10 18  1  0
  2 21  1  0
 10  9  1  0
 19 20  1  0
  6 21  1  0
 14 13  1  0
  2  3  1  0
 14 15  1  1
  3 20  1  0
  2  1  2  3
 17 18  1  0
 21 22  1  0
 10 11  1  6
  3  4  1  0
 10 19  1  0
  6  5  1  0
  5  4  1  0
  9  8  1  0
 11 12  2  0
 12 13  1  0
  8  7  1  0
 17 16  1  0
 14 16  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
  9 34  1  1
  8 32  1  0
  8 33  1  0
 19 47  1  1
  3 25  1  6
 20 48  1  0
 20 49  1  0
 11 35  1  0
  7 30  1  0
  7 31  1  0
 21 50  1  6
 13 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
  1 23  1  0
  1 24  1  0
 22 51  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol

Synonyms

Value	Source
Isoazitine	MeSH

Chemical Formula

C₂₀H₂₉NO

Average Mass

299.4580 Da

Monoisotopic Mass

299.22491 Da

IUPAC Name

(1S,2S,4S,6R,7S,10R,11R)-11-methyl-5-methylidene-13-azapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadec-13-en-6-ol

Traditional Name

(1S,2S,4S,6R,7S,10R,11R)-11-methyl-5-methylidene-13-azapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadec-13-en-6-ol

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]11C([H])([H])C([H])([H])[C@@]3([H])[C@]4(C([H])=NC([H])([H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])C4([H])[H])[C@]1([H])C2([H])[H]

InChI Identifier

InChI=1S/C20H29NO/c1-13-14-4-8-19(17(13)22)9-5-15-18(2)6-3-7-20(15,12-21-11-18)16(19)10-14/h12,14-17,22H,1,3-11H2,2H3/t14-,15+,16+,17+,18-,19-,20-/m0/s1

InChI Key

UUTPNBAAXAQHKM-YQXKYMSPSA-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
Consolida hellespontica	Plant	KNApSAcK
Consolida raveyi	LOTUS Database	35616633
Consolida raveyi Boiss Schrod	Plant	KNApSAcK
Delphinium stapeliosum	Plant	KNApSAcK
Staphisagria macrosperma	JEOL database	Diaz, J. G., et al, J. Nat. Prod. 63, 1136 (2000)

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
Alkaloid or derivatives
Tetrahydropyridine
Cyclic alcohol
Secondary alcohol
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.6	ALOGPS
logP	3.05	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	19.77	ChemAxon
pKa (Strongest Basic)	3.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.59 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.27 m³·mol⁻¹	ChemAxon
Polarizability	34.87 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10218698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12299863

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gonzalez P, Marin C, Rodriguez-Gonzalez I, Illana A, Mateo H, Longoni SS, Rosales MJ, Gonzalez-Coloma A, Reina M, Sanchez-Moreno M: Diterpenoid alkaloid derivatives as potential chemotherapeutic agents in American trypanosomiasis. Pharmacology. 2006;76(3):123-8. doi: 10.1159/000090600. Epub 2006 Jan 2. [PubMed:16391494 ]
Gonzalez P, Marin C, Rodriguez-Gonzalez I, Hitos AB, Rosales MJ, Reina M, Diaz JG, Gonzalez-Coloma A, Sanchez-Moreno M: In vitro activity of C20-diterpenoid alkaloid derivatives in promastigotes and intracellular amastigotes of Leishmania infantum. Int J Antimicrob Agents. 2005 Feb;25(2):136-41. doi: 10.1016/j.ijantimicag.2004.08.010. [PubMed:15664483 ]
Liu J, Ma D: A Unified Approach for the Assembly of Atisine- and Hetidine-type Diterpenoid Alkaloids: Total Syntheses of Azitine and the Proposed Structure of Navirine C. Angew Chem Int Ed Engl. 2018 May 28;57(22):6676-6680. doi: 10.1002/anie.201803018. Epub 2018 Apr 26. [PubMed:29611891 ]
Shrestha PM, Katz A: Diterpenoid alkaloids from the roots of Delphinium scabriflorum. J Nat Prod. 2004 Sep;67(9):1574-6. doi: 10.1021/np0305066. [PubMed:15387663 ]
Diaz, J. G., et al. (2000). Diaz, J. G., et al, J. Nat. Prod. 63, 1136 (2000). J. Nat. Prod..

Showing NP-Card for azitine (NP0029223)

MOL for NP0029223 (azitine)

3D MOL for NP0029223 (azitine)

3D SDF for NP0029223 (azitine)

3D-SDF for NP0029223 (azitine)

PDB for NP0029223 (azitine)

3D PDB for NP0029223 (azitine)

SMILES for NP0029223 (azitine)

INCHI for NP0029223 (azitine)

Structure for NP0029223 (azitine)

3D Structure for NP0029223 (azitine)