NP-MRD: Showing NP-Card for neoadenostylone (NP0036691)

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Record Information

Version

2.0

Created at

2021-06-20 19:47:53 UTC

Updated at

2021-06-30 00:08:28 UTC

NP-MRD ID

NP0036691

Secondary Accession Numbers

None

Natural Product Identification

Common Name

neoadenostylone

Provided By

JEOL Database JEOL Logo

Description

Neoadenostylone belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. neoadenostylone is found in Adenostyles alliariae, Lasiocephalus ovatus, Ligularia cyathiceps, Ligularia macrophylla, P. bellidifolia, Psacalium radulifolium, Roldana aschenborniana and Senecio polyanthemoides. neoadenostylone was first documented in 2012 (PMID: 22551074). Based on a literature review very few articles have been published on neoadenostylone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121473D          

 48 50  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121473D          

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 10 11  1  0  0  0  0
 17 18  2  0  0  0  0
 21 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  6  0  0  0
  8  7  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  2 28  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
 20 40  1  0  0  0  0
 20 41  1  0  0  0  0
 21 42  1  1  0  0  0
 18 37  1  0  0  0  0
  8 32  1  1  0  0  0
 12 36  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 22 43  1  0  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 24 46  1  0  0  0  0
 24 47  1  0  0  0  0
 24 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036691

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\C(=O)O[C@]1([H])C2=C(OC([H])=C2C([H])([H])[H])C(=O)C2=C([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@@]12C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-6-11(2)19(22)24-18-15-12(3)10-23-17(15)16(21)14-9-7-8-13(4)20(14,18)5/h6,9-10,13,18H,7-8H2,1-5H3/b11-6-/t13-,18+,20+/m0/s1

> <INCHI_KEY>
ZGPJMFUBGMSEDV-OLQHVUIGSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.408

> <EXACT_MASS>
328.167459253

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.28584487750167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,4aR,5S)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
4.685697048333335

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.940805698844561

> <JCHEM_POLAR_SURFACE_AREA>
56.51

> <JCHEM_REFRACTIVITY>
93.37259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,5S)-3,4a,5-trimethyl-9-oxo-4H,5H,6H,7H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
   -3.8141    3.4664    0.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6547    2.0769    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507    1.3030    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5556   -0.0662   -0.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833    1.7466    0.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154    2.5130    1.7641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309    1.1573    0.1987 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0854    1.5504    0.6337 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7379    2.3885   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267    3.3982   -1.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1546    3.9262   -1.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085    3.8096   -2.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    3.1496   -1.7154 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870    2.2991   -0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0578    1.4579   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2548    1.4243   -0.3443 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719    0.5882    1.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3249    0.1646    1.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -0.7074    3.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5628   -1.3405    2.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269   -0.3372    2.3815 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1545   -1.0191    2.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9603    0.2520    0.9725 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7744   -0.8136   -0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3234    3.4425    1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689    4.0032    0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4302    4.0497    0.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5602    1.6790   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061   -0.0952   -1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5584   -0.3670   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079   -0.8160    0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0473    2.1738    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8327    3.1560   -1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5113    4.2684   -0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019    4.7784   -2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4314    4.5390   -2.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740    0.4593    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6817   -1.4999    3.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503   -0.1040    4.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -1.7336    3.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -2.2072    2.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4887    0.5016    3.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0966   -1.8856    1.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494   -1.3804    3.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551   -0.3351    2.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0841   -0.4353   -1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3706   -1.7118    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -1.1286   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  7  5  1  0
  2  1  1  0
 19 20  1  0
 17 15  1  0
 23  8  1  0
  8  9  1  0
 14 15  1  0
 14  9  2  0
  5  6  2  0
  3  4  1  0
  5  3  1  0
 19 18  1  0
  9 10  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 20 21  1  0
 15 16  2  0
 21 23  1  0
 10 11  1  0
 17 18  2  0
 21 22  1  0
 17 23  1  0
 23 24  1  6
  8  7  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  2 28  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  1
 18 37  1  0
  8 32  1  1
 12 36  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  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      -3.814   3.466   0.696  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.655   2.077   0.163  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.551   1.303   0.165  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.556  -0.066  -0.454  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.283   1.747   0.818  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.215   2.513   1.764  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.231   1.157   0.199  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.085   1.550   0.634  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.738   2.389  -0.440  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.227   3.398  -1.317  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.155   3.926  -1.422  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.309   3.810  -2.073  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.437   3.150  -1.715  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.087   2.299  -0.719  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.058   1.458  -0.075  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.255   1.424  -0.344  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.472   0.588   1.015  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.325   0.165   1.966  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.936  -0.707   3.111  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.563  -1.341   2.932  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.527  -0.337   2.381  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.155  -1.019   2.437  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.960   0.252   0.973  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.774  -0.814  -0.142  0.00  0.00           C+0
HETATM   25  H   UNK     0      -4.323   3.442   1.664  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.869   4.003   0.800  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.430   4.050   0.004  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.560   1.679  -0.294  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.906  -0.095  -1.335  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.558  -0.367  -0.776  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.208  -0.816   0.263  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.047   2.174   1.537  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.833   3.156  -1.801  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.511   4.268  -0.446  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.202   4.778  -2.108  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.431   4.539  -2.863  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.374   0.459   1.932  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.682  -1.500   3.239  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.950  -0.104   4.027  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.235  -1.734   3.903  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.641  -2.207   2.264  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.489   0.502   3.092  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.097  -1.886   1.772  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.049  -1.380   3.452  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.655  -0.335   2.193  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.084  -0.435  -1.123  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.371  -1.712   0.053  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.732  -1.129  -0.244  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1   28                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3   29   30   31                                             
CONECT    5    7    6    3                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8   23    9    7   32                                             
CONECT    9    8   14   10                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10   33   34   35                                             
CONECT   12   10   13   36                                                  
CONECT   13   12   14                                                       
CONECT   14   15    9   13                                                  
CONECT   15   17   14   16                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   19   17   37                                                  
CONECT   19   20   18   38   39                                             
CONECT   20   19   21   40   41                                             
CONECT   21   20   23   22   42                                             
CONECT   22   21   43   44   45                                             
CONECT   23    8   21   17   24                                             
CONECT   24   23   46   47   48                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    8                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   12                                                            
CONECT   37   18                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   20                                                            
CONECT   42   21                                                            
CONECT   43   22                                                            
CONECT   44   22                                                            
CONECT   45   22                                                            
CONECT   46   24                                                            
CONECT   47   24                                                            
CONECT   48   24                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  100    0
END

RDKit          3D

48 50  0  0  0  0  0  0  0  0999 V2000
   -3.8141    3.4664    0.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6547    2.0769    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507    1.3030    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5556   -0.0662   -0.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833    1.7466    0.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154    2.5130    1.7641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309    1.1573    0.1987 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0854    1.5504    0.6337 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7379    2.3885   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267    3.3982   -1.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1546    3.9262   -1.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085    3.8096   -2.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    3.1496   -1.7154 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870    2.2991   -0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0578    1.4579   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2548    1.4243   -0.3443 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719    0.5882    1.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3249    0.1646    1.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -0.7074    3.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5628   -1.3405    2.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269   -0.3372    2.3815 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1545   -1.0191    2.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9603    0.2520    0.9725 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7744   -0.8136   -0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3234    3.4425    1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689    4.0032    0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4302    4.0497    0.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5602    1.6790   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061   -0.0952   -1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5584   -0.3670   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079   -0.8160    0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0473    2.1738    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8327    3.1560   -1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5113    4.2684   -0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019    4.7784   -2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4314    4.5390   -2.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740    0.4593    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6817   -1.4999    3.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503   -0.1040    4.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -1.7336    3.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -2.2072    2.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4887    0.5016    3.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0966   -1.8856    1.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494   -1.3804    3.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551   -0.3351    2.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0841   -0.4353   -1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3706   -1.7118    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -1.1286   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  7  5  1  0
  2  1  1  0
 19 20  1  0
 17 15  1  0
 23  8  1  0
  8  9  1  0
 14 15  1  0
 14  9  2  0
  5  6  2  0
  3  4  1  0
  5  3  1  0
 19 18  1  0
  9 10  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 20 21  1  0
 15 16  2  0
 21 23  1  0
 10 11  1  0
 17 18  2  0
 21 22  1  0
 17 23  1  0
 23 24  1  6
  8  7  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  2 28  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  1
 18 37  1  0
  8 32  1  1
 12 36  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₄

Average Mass

328.4080 Da

Monoisotopic Mass

328.16746 Da

IUPAC Name

(4S,4aR,5S)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(4S,4aR,5S)-3,4a,5-trimethyl-9-oxo-4H,5H,6H,7H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\C(=O)O[C@]1([H])C2=C(OC([H])=C2C([H])([H])[H])C(=O)C2=C([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@@]12C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H24O4/c1-6-11(2)19(22)24-18-15-12(3)10-23-17(15)16(21)14-9-7-8-13(4)20(14,18)5/h6,9-10,13,18H,7-8H2,1-5H3/b11-6-/t13-,18+,20+/m0/s1

InChI Key

ZGPJMFUBGMSEDV-OLQHVUIGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Adenostyles alliariae	Plant	KNApSAcK
Lasiocephalus ovatus	LOTUS Database	35616633
Ligularia cyathiceps	LOTUS Database	35616633
Ligularia macrophylla	LOTUS Database	35616633
Primula bellidifolia	JEOL database	Fragoso-Serrano, M., et al, J. Nat. Prod. 75, 890 (2012)
Psacalium radulifolium	Plant	KNApSAcK
Roldana aschenborniana	LOTUS Database	35616633
Senecio polyanthemoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Aryl ketone
Fatty acid ester
Fatty acyl
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Aldehyde
Organic oxygen compound
Carbonyl group
Organooxygen 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	4.57	ALOGPS
logP	4.69	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	56.51 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.37 m³·mol⁻¹	ChemAxon
Polarizability	36.29 Å³	ChemAxon
Number of Rings	3	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

4946459

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6442373

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fragoso-Serrano M, Figueroa-Gonzalez G, Castro-Carranza E, Hernandez-Solis F, Linares E, Bye R, Pereda-Miranda R: Profiling of alkaloids and eremophilanes in miracle tea (Packera candidissima and P. bellidifolia) products. J Nat Prod. 2012 May 25;75(5):890-5. doi: 10.1021/np2009412. Epub 2012 May 2. [PubMed:22551074 ]
Fragoso-Serrano, M., et al. (2012). Fragoso-Serrano, M., et al, J. Nat. Prod. 75, 890 (2012). J. Nat. Prod..

Showing NP-Card for neoadenostylone (NP0036691)

MOL for NP0036691 (neoadenostylone)

3D MOL for NP0036691 (neoadenostylone)

3D SDF for NP0036691 (neoadenostylone)

3D-SDF for NP0036691 (neoadenostylone)

PDB for NP0036691 (neoadenostylone)

3D PDB for NP0036691 (neoadenostylone)

SMILES for NP0036691 (neoadenostylone)

INCHI for NP0036691 (neoadenostylone)

Structure for NP0036691 (neoadenostylone)

3D Structure for NP0036691 (neoadenostylone)