NP-MRD: Showing NP-Card for tagalsin A (NP0031257)

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Record Information

Version

2.0

Created at

2021-06-19 22:23:33 UTC

Updated at

2021-06-29 23:59:43 UTC

NP-MRD ID

NP0031257

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tagalsin A

Provided By

JEOL Database JEOL Logo

Description

TAGALSIN A belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. tagalsin A is found in Ceriops tagal. tagalsin A was first documented in 2011 (PMID: 21775935). Based on a literature review very few articles have been published on TAGALSIN A (PMID: 28964872).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100233D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202100233D          

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   -2.3547   -1.8794   -0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072   -0.5546   -1.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6715   -0.0652   -2.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  2  0  0  0  0
  7  6  1  0  0  0  0
  9 23  1  0  0  0  0
 23  3  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
 18 20  1  0  0  0  0
 18 19  2  0  0  0  0
 14  7  1  0  0  0  0
 16 17  1  0  0  0  0
 12 11  1  0  0  0  0
 20 21  1  0  0  0  0
 11 10  1  0  0  0  0
  7  8  1  6  0  0  0
 10  9  1  0  0  0  0
  3  2  1  6  0  0  0
  7  9  1  0  0  0  0
  2  1  2  3  0  0  0
 20 12  1  0  0  0  0
  3  4  1  0  0  0  0
 14 15  1  0  0  0  0
  9 37  1  1  0  0  0
 14 12  1  0  0  0  0
 14 45  1  1  0  0  0
 12 13  1  1  0  0  0
 16 18  1  0  0  0  0
 20 22  1  1  0  0  0
 22 21  1  0  0  0  0
 15 46  1  0  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
 17 47  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
  2 26  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031257

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])[C@]2([H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@](C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])[C@]3([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]2(OC2([H])[H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-5-17(2)8-9-18(3)13(11-17)6-7-19(4)15(18)10-14(21)16(22)20(19)12-23-20/h5,10,13,15,21H,1,6-9,11-12H2,2-4H3/t13-,15+,17-,18-,19-,20-/m0/s1

> <INCHI_KEY>
XJFGTYYCVFPPMQ-JXCDLVPQSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.607908628317965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4'aR,4'bS,7'S,8'aS,10'aS)-7'-ethenyl-3'-hydroxy-4'b,7',10'a-trimethyl-4'a,4'b,5',6',7',8',8'a,9',10',10'a-decahydro-2'H-spiro[oxirane-2,1'-phenanthrene]-2'-one

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
4.126401479

> <ALOGPS_LOGS>
-5.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.136263826852515

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7320582021348114

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
91.00619999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.99e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4'aR,4'bS,7'S,8'aS,10'aS)-7'-ethenyl-3'-hydroxy-4'b,7',10'a-trimethyl-5',6',8',8'a,9',10'-hexahydro-4'aH-spiro[oxirane-2,1'-phenanthrene]-2'-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    4.7154    0.8556   -3.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5627    1.7784   -2.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    1.6041   -1.5750 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0783    1.8351   -0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547    2.6960   -1.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    2.5518   -0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3475    1.1480    0.0267 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3019    0.9751   -1.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4851    0.0939   -0.0617 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9501   -1.3251    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -1.4728    1.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2394   -0.4256    1.8872 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1252   -0.4609    3.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808    1.0271    1.4559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4347    2.0318    1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7378    1.7359    1.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903    2.7246    1.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2125    0.3458    1.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140    0.1430    1.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719   -0.7361    1.3263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4700   -1.9228    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697   -2.0130    1.8077 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3103    0.2015   -1.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951   -0.1737   -3.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1840    1.1192   -4.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9331    2.7815   -3.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299    1.8070    0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542    2.8123   -0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8592    1.0720   -0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214    3.6906   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1908    2.6979   -2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2331    3.3328   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6300    2.7715    0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.0039   -2.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2339    0.0281   -1.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446    1.7765   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780    0.2775    0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7755   -2.0438    0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2424   -1.5927   -0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -1.3891    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9441   -2.4942    1.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658    0.1960    3.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0643   -0.1532    3.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1039   -1.4724    3.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4645    1.3204    2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475    3.0685    1.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5518    2.2659    1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6795   -2.5206   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547   -1.8794   -0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072   -0.5546   -1.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6715   -0.0652   -2.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  2  0
  7  6  1  0
  9 23  1  0
 23  3  1  0
  3  5  1  0
  5  6  1  0
 18 20  1  0
 18 19  2  0
 14  7  1  0
 16 17  1  0
 12 11  1  0
 20 21  1  0
 11 10  1  0
  7  8  1  6
 10  9  1  0
  3  2  1  6
  7  9  1  0
  2  1  2  3
 20 12  1  0
  3  4  1  0
 14 15  1  0
  9 37  1  1
 14 12  1  0
 14 45  1  1
 12 13  1  1
 16 18  1  0
 20 22  1  1
 22 21  1  0
 15 46  1  0
 11 40  1  0
 11 41  1  0
 10 38  1  0
 10 39  1  0
 23 50  1  0
 23 51  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
 17 47  1  0
 21 48  1  0
 21 49  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  2 26  1  0
  1 24  1  0
  1 25  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
 13 42  1  0
 13 43  1  0
 13 44  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       4.715   0.856  -3.920  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.563   1.778  -2.960  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.938   1.604  -1.575  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.078   1.835  -0.557  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.855   2.696  -1.407  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.003   2.552  -0.139  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.347   1.148   0.027  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.302   0.975  -1.106  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.485   0.094  -0.062  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.950  -1.325   0.137  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.324  -1.473   1.522  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.239  -0.426   1.887  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.125  -0.461   3.447  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.681   1.027   1.456  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.435   2.032   1.651  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.738   1.736   1.624  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.690   2.725   1.779  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.212   0.346   1.381  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.414   0.143   1.218  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.172  -0.736   1.326  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.470  -1.923   0.402  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.670  -2.013   1.808  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.310   0.202  -1.357  0.00  0.00           C+0
HETATM   24  H   UNK     0       4.395  -0.174  -3.805  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.184   1.119  -4.864  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.933   2.781  -3.179  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.730   1.807   0.479  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.554   2.812  -0.706  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.859   1.072  -0.661  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.321   3.691  -1.395  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.191   2.698  -2.281  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.233   3.333  -0.160  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.630   2.772   0.735  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.754   1.004  -2.102  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.234   0.028  -1.044  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.445   1.777  -1.087  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.178   0.278   0.771  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.776  -2.044   0.056  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.242  -1.593  -0.652  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.148  -1.389   2.245  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.944  -2.494   1.642  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.666   0.196   3.823  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.064  -0.153   3.921  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.104  -1.472   3.803  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.464   1.320   2.172  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.148   3.068   1.813  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.552   2.266   1.676  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.680  -2.521  -0.026  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.355  -1.879  -0.226  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.107  -0.555  -1.334  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.672  -0.065  -2.208  0.00  0.00           H+0
CONECT    1    2   24   25                                                  
CONECT    2    3    1   26                                                  
CONECT    3   23    5    2    4                                             
CONECT    4    3   27   28   29                                             
CONECT    5    3    6   30   31                                             
CONECT    6    7    5   32   33                                             
CONECT    7    6   14    8    9                                             
CONECT    8    7   34   35   36                                             
CONECT    9   23   10    7   37                                             
CONECT   10   11    9   38   39                                             
CONECT   11   12   10   40   41                                             
CONECT   12   11   20   14   13                                             
CONECT   13   12   42   43   44                                             
CONECT   14    7   15   12   45                                             
CONECT   15   16   14   46                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   47                                                       
CONECT   18   20   19   16                                                  
CONECT   19   18                                                            
CONECT   20   18   21   12   22                                             
CONECT   21   20   22   48   49                                             
CONECT   22   20   21                                                       
CONECT   23    9    3   50   51                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    4                                                            
CONECT   28    4                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   17                                                            
CONECT   48   21                                                            
CONECT   49   21                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  108    0
END

RDKit          3D

51 54  0  0  0  0  0  0  0  0999 V2000
    4.7154    0.8556   -3.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5627    1.7784   -2.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    1.6041   -1.5750 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0783    1.8351   -0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547    2.6960   -1.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    2.5518   -0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3475    1.1480    0.0267 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3019    0.9751   -1.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4851    0.0939   -0.0617 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9501   -1.3251    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -1.4728    1.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2394   -0.4256    1.8872 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1252   -0.4609    3.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808    1.0271    1.4559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4347    2.0318    1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7378    1.7359    1.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903    2.7246    1.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2125    0.3458    1.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140    0.1430    1.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719   -0.7361    1.3263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4700   -1.9228    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697   -2.0130    1.8077 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3103    0.2015   -1.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951   -0.1737   -3.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1840    1.1192   -4.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9331    2.7815   -3.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299    1.8070    0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542    2.8123   -0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8592    1.0720   -0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214    3.6906   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1908    2.6979   -2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2331    3.3328   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6300    2.7715    0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.0039   -2.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2339    0.0281   -1.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446    1.7765   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780    0.2775    0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7755   -2.0438    0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2424   -1.5927   -0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -1.3891    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9441   -2.4942    1.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658    0.1960    3.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0643   -0.1532    3.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1039   -1.4724    3.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4645    1.3204    2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475    3.0685    1.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5518    2.2659    1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6795   -2.5206   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547   -1.8794   -0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072   -0.5546   -1.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6715   -0.0652   -2.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  2  0
  7  6  1  0
  9 23  1  0
 23  3  1  0
  3  5  1  0
  5  6  1  0
 18 20  1  0
 18 19  2  0
 14  7  1  0
 16 17  1  0
 12 11  1  0
 20 21  1  0
 11 10  1  0
  7  8  1  6
 10  9  1  0
  3  2  1  6
  7  9  1  0
  2  1  2  3
 20 12  1  0
  3  4  1  0
 14 15  1  0
  9 37  1  1
 14 12  1  0
 14 45  1  1
 12 13  1  1
 16 18  1  0
 20 22  1  1
 22 21  1  0
 15 46  1  0
 11 40  1  0
 11 41  1  0
 10 38  1  0
 10 39  1  0
 23 50  1  0
 23 51  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
 17 47  1  0
 21 48  1  0
 21 49  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  2 26  1  0
  1 24  1  0
  1 25  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4410 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(2S,4'aR,4'bS,7'S,8'aS,10'aS)-7'-ethenyl-3'-hydroxy-4'b,7',10'a-trimethyl-4'a,4'b,5',6',7',8',8'a,9',10',10'a-decahydro-2'H-spiro[oxirane-2,1'-phenanthrene]-2'-one

Traditional Name

(2S,4'aR,4'bS,7'S,8'aS,10'aS)-7'-ethenyl-3'-hydroxy-4'b,7',10'a-trimethyl-5',6',8',8'a,9',10'-hexahydro-4'aH-spiro[oxirane-2,1'-phenanthrene]-2'-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])[C@]2([H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@](C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])[C@]3([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]2(OC2([H])[H])C1=O

InChI Identifier

InChI=1S/C20H28O3/c1-5-17(2)8-9-18(3)13(11-17)6-7-19(4)15(18)10-14(21)16(22)20(19)12-23-20/h5,10,13,15,21H,1,6-9,11-12H2,2-4H3/t13-,15+,17-,18-,19-,20-/m0/s1

InChI Key

XJFGTYYCVFPPMQ-JXCDLVPQSA-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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Ceriops tagal	JEOL database	Zhang, Y., et al, Phytochemistry 66, 1465 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Phenanthrene
Cyclohexenone
Ketone
Dialkyl ether
Enol
Oxirane
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	3.33	ALOGPS
logP	4.13	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.01 m³·mol⁻¹	ChemAxon
Polarizability	35.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

9697361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11522574

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Du SS, Wang CF, Li J, Zhang HM, Liu QZ, Liu ZL, Deng ZW: Antifeedant diterpenoids against Tribolium castaneum from the stems and twigs of Ceriops tagal (Rhizophoraceae). Molecules. 2011 Jul 20;16(7):6060-7. doi: 10.3390/molecules16076060. [PubMed:21775935 ]
Zhang X, Li W, Shen L, Wu J: Four new diterpenes from the mangrove Ceriops tagal and structure revision of four dolabranes with a 4,18-epoxy group. Fitoterapia. 2018 Jan;124:1-7. doi: 10.1016/j.fitote.2017.09.019. Epub 2017 Sep 28. [PubMed:28964872 ]
Zhang, Y., et al. (2005). Zhang, Y., et al, Phytochemistry 66, 1465 (2005) . Phytochem..

Showing NP-Card for tagalsin A (NP0031257)

MOL for NP0031257 (tagalsin A)

3D MOL for NP0031257 (tagalsin A)

3D SDF for NP0031257 (tagalsin A)

3D-SDF for NP0031257 (tagalsin A)

PDB for NP0031257 (tagalsin A)

3D PDB for NP0031257 (tagalsin A)

SMILES for NP0031257 (tagalsin A)

INCHI for NP0031257 (tagalsin A)

Structure for NP0031257 (tagalsin A)

3D Structure for NP0031257 (tagalsin A)