NP-MRD: Showing NP-Card for Candelalide A (NP0003722)

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Record Information

Version

2.0

Created at

2020-12-09 00:53:40 UTC

Updated at

2021-07-15 16:47:12 UTC

NP-MRD ID

NP0003722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Candelalide A

Provided By

NPAtlas

Description

Candelalide A belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Candelalide A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Candelalide A is found in Clonostachys candelabrum and Sesquicillium. Candelalide A was first documented in 2005 (PMID: 16092865). Based on a literature review a small amount of articles have been published on candelalide A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117493D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242117493D          

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    4.6432   -2.8734   -0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9033   -2.3532   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1674   -1.6981    1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4043   -1.0664    0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0361    0.7277    2.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6933    2.4596    1.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6226   -0.5304   -1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926    1.7511   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671    1.2857   -2.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372   -0.5113   -2.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0817    0.9129   -2.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675   -2.4242   -2.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1040   -3.6839   -1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7005   -0.1068    0.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1071    4.0970    0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6726    3.5215   -0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3172    3.3110    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 17  2  1  0  0  0  0
 28 19  1  0  0  0  0
 15  5  1  0  0  0  0
 12  6  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
  5 36  1  1  0  0  0
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  7 39  1  0  0  0  0
  8 40  1  0  0  0  0
  8 41  1  0  0  0  0
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 25 60  1  0  0  0  0
 27 61  1  0  0  0  0
 27 62  1  0  0  0  0
 27 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C([H])([H])C([H])([H])[C@@]2([H])[C@]3(C([H])([H])[H])C([H])([H])C([H])=C([H])O[C@]3([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@]1([H])C([H])([H])C1=C(OC([H])([H])[H])OC(=C(C1=O)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O4/c1-15-8-9-20-24(4,12-10-21-25(20,5)11-7-13-28-21)19(15)14-18-22(26)16(2)17(3)29-23(18)27-6/h7,13,19-21H,1,8-12,14H2,2-6H3/t19-,20-,21-,24-,25+/m1/s1

> <INCHI_KEY>
SCHPGLGCBCJZKD-YYHYCTJNSA-N

> <FORMULA>
C25H34O4

> <MOLECULAR_WEIGHT>
398.543

> <EXACT_MASS>
398.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.2839410650476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(4aR,6aR,7R,10aR,10bS)-6a,10b-dimethyl-8-methylidene-1H,4aH,5H,6H,6aH,7H,8H,9H,10H,10aH,10bH-cyclohexa[f]chromen-7-yl]methyl}-2-methoxy-5,6-dimethyl-4H-pyran-4-one

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
5.1005652266666655

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5156778722096025

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
125.80099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(4aR,6aR,7R,10aR,10bS)-6a,10b-dimethyl-8-methylidene-1H,4aH,5H,6H,7H,9H,10H,10aH-cyclohexa[f]chromen-7-yl]methyl}-2-methoxy-5,6-dimethylpyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
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    4.1674   -1.6981    1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4671    1.2857   -2.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5675   -2.4242   -2.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
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 23 24  1  0
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 24 26  2  0
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 26 28  1  0
 28 29  2  0
 17  2  1  0
 28 19  1  0
 15  5  1  0
 12  6  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  1
  7 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
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  9 42  1  0
 10 43  1  0
 12 44  1  6
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 22 55  1  0
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 25 58  1  0
 25 59  1  0
 25 60  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       0.158   2.028   0.935  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.133   0.731   0.821  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.463  -0.166   2.018  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.476  -1.207   1.480  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.103  -0.619   0.252  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.499  -1.022  -0.041  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.686  -2.420  -0.567  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.336  -0.913   1.201  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.307   0.463   1.750  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.667   1.405   0.856  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.990   0.893  -0.394  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.068   0.006  -1.030  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.016   0.863  -1.652  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.762   0.155  -2.051  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.173  -0.633  -0.941  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.846  -2.006  -1.435  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.147  -0.051  -0.397  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.060   0.508  -1.395  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.415   0.699  -0.841  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.204  -0.428  -0.579  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.685  -1.715  -0.825  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.498  -2.836  -0.552  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.419  -0.293  -0.109  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.005   0.845   0.156  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.405   0.910   0.695  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.316   1.994  -0.070  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.912   3.331   0.204  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.011   1.904  -0.573  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.418   2.993  -0.770  0.00  0.00           O+0
HETATM   30  H   UNK     0       0.424   2.430   1.927  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.029   2.726   0.155  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.443  -0.658   2.407  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.884   0.477   2.779  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.966  -2.166   1.315  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.197  -1.338   2.283  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.188   0.494   0.485  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.907  -3.129  -0.303  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.643  -2.873  -0.165  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.903  -2.353  -1.673  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.167  -1.698   1.943  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.404  -1.066   0.859  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.036   0.728   2.743  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.693   2.460   1.118  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.623  -0.530  -1.850  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.793   1.751  -1.027  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.467   1.286  -2.598  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.037  -0.511  -2.923  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.082   0.913  -2.489  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.567  -2.424  -2.160  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.105  -1.916  -2.027  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.575  -2.712  -0.617  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.738  -0.961   0.030  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.193  -0.234  -2.220  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.748   1.501  -1.805  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.514  -3.070   0.536  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.104  -3.684  -1.141  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.559  -2.584  -0.847  0.00  0.00           H+0
HETATM   58  H   UNK     0      -7.034   1.268  -0.144  0.00  0.00           H+0
HETATM   59  H   UNK     0      -6.700  -0.107   0.998  0.00  0.00           H+0
HETATM   60  H   UNK     0      -6.482   1.635   1.531  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.107   4.097   0.189  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.673   3.522  -0.574  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.317   3.311   1.230  0.00  0.00           H+0
CONECT    1    2   30   31                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4   32   33                                             
CONECT    4    3    5   34   35                                             
CONECT    5    4    6   15   36                                             
CONECT    6    5    7    8   12                                             
CONECT    7    6   37   38   39                                             
CONECT    8    6    9   40   41                                             
CONECT    9    8   10   42                                                  
CONECT   10    9   11   43                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13    6   44                                             
CONECT   13   12   14   45   46                                             
CONECT   14   13   15   47   48                                             
CONECT   15   14   16   17    5                                             
CONECT   16   15   49   50   51                                             
CONECT   17   15   18    2   52                                             
CONECT   18   17   19   53   54                                             
CONECT   19   18   20   28                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   55   56   57                                             
CONECT   23   20   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   58   59   60                                             
CONECT   26   24   27   28                                                  
CONECT   27   26   61   62   63                                             
CONECT   28   26   29   19                                                  
CONECT   29   28                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   16                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   17                                                            
CONECT   53   18                                                            
CONECT   54   18                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   25                                                            
CONECT   59   25                                                            
CONECT   60   25                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   27                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  132    0
END

RDKit          3D

63 66  0  0  0  0  0  0  0  0999 V2000
    0.1583    2.0277    0.9349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1328    0.7309    0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4632   -0.1663    2.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765   -1.2069    1.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1030   -0.6186    0.2519 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4994   -1.0218   -0.0405 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6862   -2.4199   -0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3358   -0.9134    1.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3071    0.4629    1.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6673    1.4053    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0678    0.0062   -1.0303 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0164    0.8629   -1.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620    0.1552   -2.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725   -0.6331   -0.9413 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.4149    0.6993   -0.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4052    0.9098    0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3156    1.9945   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9117    3.3312    0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0109    1.9043   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4183    2.9926   -0.7695 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0292    2.7258    0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8839    0.4769    2.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9655   -2.1661    1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1969   -1.3378    2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885    0.4943    0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -3.1294   -0.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432   -2.8734   -0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9033   -2.3532   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1674   -1.6981    1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4043   -1.0664    0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0361    0.7277    2.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6933    2.4596    1.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6226   -0.5304   -1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926    1.7511   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671    1.2857   -2.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372   -0.5113   -2.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0817    0.9129   -2.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675   -2.4242   -2.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1045   -1.9162   -2.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752   -2.7122   -0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379   -0.9611    0.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -0.2344   -2.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    1.5008   -1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5142   -3.0700    0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1040   -3.6839   -1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5593   -2.5841   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0344    1.2683   -0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7005   -0.1068    0.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4818    1.6350    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071    4.0970    0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6726    3.5215   -0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3172    3.3110    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 17  2  1  0
 28 19  1  0
 15  5  1  0
 12  6  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  1
  7 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 12 44  1  6
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 13 46  1  0
 14 47  1  0
 14 48  1  0
 16 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  1
 18 53  1  0
 18 54  1  0
 22 55  1  0
 22 56  1  0
 22 57  1  0
 25 58  1  0
 25 59  1  0
 25 60  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-Candelalide a	ChEBI

Chemical Formula

C₂₅H₃₄O₄

Average Mass

398.5430 Da

Monoisotopic Mass

398.24571 Da

IUPAC Name

3-{[(4aR,6aR,7R,10aR,10bS)-6a,10b-dimethyl-8-methylidene-1H,4aH,5H,6H,6aH,7H,8H,9H,10H,10aH,10bH-cyclohexa[f]chromen-7-yl]methyl}-2-methoxy-5,6-dimethyl-4H-pyran-4-one

Traditional Name

3-{[(4aR,6aR,7R,10aR,10bS)-6a,10b-dimethyl-8-methylidene-1H,4aH,5H,6H,7H,9H,10H,10aH-cyclohexa[f]chromen-7-yl]methyl}-2-methoxy-5,6-dimethylpyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(C[C@@H]2C(=C)CC[C@@H]3[C@]2(C)CC[C@H]2OC=CC[C@@]32C)C(=O)C(C)=C(C)O1

InChI Identifier

InChI=1S/C25H34O4/c1-15-8-9-20-24(4,12-10-21-25(20,5)11-7-13-28-21)19(15)14-18-22(26)16(2)17(3)29-23(18)27-6/h7,13,19-21H,1,8-12,14H2,2-6H3/t19-,20-,21-,24-,25+/m1/s1

InChI Key

SCHPGLGCBCJZKD-YYHYCTJNSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Clonostachys candelabrum	LOTUS Database	35616633
Sesquicillium	NPAtlas	11430046

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Pyranone
Alkyl aryl ether
Pyran
Heteroaromatic compound
Vinylogous ester
Cyclic ketone
Oxacycle
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:65571 )
pyranone (CHEBI:65571 )
cyclic ether (CHEBI:65571 )
diterpenoid (CHEBI:65571 )

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	5.18	ALOGPS
logP	5.1	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	125.8 m³·mol⁻¹	ChemAxon
Polarizability	45.28 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA004208

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8986204

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

65571

Good Scents ID

Not Available

References

General References

Watanabe K, Iwasaki K, Abe T, Inoue M, Ohkubo K, Suzuki T, Katoh T: Enantioselective total synthesis of (-)-candelalide A, a novel blocker of the voltage-gated potassium channel Kv1.3 for an immunosuppressive agent. Org Lett. 2005 Aug 18;7(17):3745-8. doi: 10.1021/ol051398c. [PubMed:16092865 ]

Showing NP-Card for Candelalide A (NP0003722)

MOL for NP0003722 (Candelalide A)

3D MOL for NP0003722 (Candelalide A)

3D SDF for NP0003722 (Candelalide A)

3D-SDF for NP0003722 (Candelalide A)

PDB for NP0003722 (Candelalide A)

3D PDB for NP0003722 (Candelalide A)

SMILES for NP0003722 (Candelalide A)

INCHI for NP0003722 (Candelalide A)

Structure for NP0003722 (Candelalide A)

3D Structure for NP0003722 (Candelalide A)