NP-MRD: Showing NP-Card for steviol (NP0030224)

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Record Information

Version

2.0

Created at

2021-06-19 21:38:07 UTC

Updated at

2021-08-20 00:00:16 UTC

NP-MRD ID

NP0030224

Secondary Accession Numbers

None

Natural Product Identification

Common Name

steviol

Provided By

JEOL Database JEOL Logo

Description

steviol is found in Bruguiera gymnorhiza and Ceriops decandra. steviol was first documented in 2021 (PMID: 34377189). Based on a literature review a significant number of articles have been published on Steviol (PMID: 34363125) (PMID: 34319319) (PMID: 34279430) (PMID: 34247737) (PMID: 34196745) (PMID: 34178968).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306192123383D          

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     RDKit          3D

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  Mrv1652306192123383D          

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    2.7402   -5.1980    0.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7646    0.5732    1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688    1.9164   -0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323    0.5011   -1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853    2.6695   -2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8014    1.2741   -1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618    4.0207   -0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2301    2.1579    1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9998    0.8561    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
 18 19  1  0  0  0  0
  4 23  1  0  0  0  0
 21 20  1  0  0  0  0
 20 19  1  0  0  0  0
 12 13  1  0  0  0  0
  4  3  1  1  0  0  0
  8 18  1  0  0  0  0
 21  2  1  0  0  0  0
  2  3  1  0  0  0  0
  7  6  1  0  0  0  0
 21 22  1  6  0  0  0
  6  5  1  0  0  0  0
  8  9  1  6  0  0  0
  5  4  1  0  0  0  0
 13 14  1  0  0  0  0
 18  4  1  0  0  0  0
 13 15  1  6  0  0  0
  7 13  1  0  0  0  0
  2  1  2  3  0  0  0
  8 10  1  0  0  0  0
 15 16  2  0  0  0  0
  8  7  1  0  0  0  0
 15 17  1  0  0  0  0
  7 32  1  1  0  0  0
 11 12  1  0  0  0  0
 18 46  1  1  0  0  0
 21 23  1  0  0  0  0
 11 38  1  0  0  0  0
 11 39  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
 23 52  1  0  0  0  0
 23 53  1  0  0  0  0
 20 49  1  0  0  0  0
 20 50  1  0  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
 22 51  1  0  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
 14 42  1  0  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 17 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@@]4(O[H])C(=C([H])[H])C([H])([H])[C@@]3(C4([H])[H])C([H])([H])C([H])([H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)/t14-,15-,17+,18+,19+,20-/m0/s1

> <INCHI_KEY>
QFVOYBUQQBFCRH-VQSWZGCSSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.013434996605426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,5R,9S,10R,13S)-13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.6485309993333326

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.28616542238373

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.704006032449091

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9240323527129165

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
88.89169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5R,9S,10R,13S)-13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    0.7577    4.8470    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773    3.5623    0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392    2.7483    1.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042    1.3192    1.4652 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4946    0.6138    2.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455   -0.8608    2.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011   -1.6160    1.9372 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4616   -1.0688    0.4807 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6233   -1.4024   -0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8249   -1.7582   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8147   -3.2818    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439   -3.7623    1.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502   -3.1803    2.0718 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7529   -3.6094    3.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259   -3.7946    1.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1649   -3.3843    1.6507 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8349   -4.9312    0.7973 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002    0.5014    0.5681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0528    1.1939   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1421    1.9614   -1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556    2.6951   -0.3153 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0092    3.4231   -0.9110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853    1.6897    0.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1273    5.3911    1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103    5.3781   -0.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0897    3.1721    2.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4492    2.7441    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151    0.6960    3.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114    1.1191    3.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906   -0.9577    2.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0192   -1.2605    3.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2048   -1.3327    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7004   -2.4709   -0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961   -1.1030   -0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878   -0.9281   -1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7021   -1.3891    0.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873   -1.4949   -1.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -3.7087   -0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7905   -3.6641   -0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4032   -3.4742    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5300   -4.8594    1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0576   -3.1266    4.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6980   -3.3710    4.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6211   -4.6945    3.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7402   -5.1980    0.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7646    0.5732    1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688    1.9164   -0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323    0.5011   -1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853    2.6695   -2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8014    1.2741   -1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618    4.0207   -0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2301    2.1579    1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9998    0.8561    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 18 19  1  0
  4 23  1  0
 21 20  1  0
 20 19  1  0
 12 13  1  0
  4  3  1  1
  8 18  1  0
 21  2  1  0
  2  3  1  0
  7  6  1  0
 21 22  1  6
  6  5  1  0
  8  9  1  6
  5  4  1  0
 13 14  1  0
 18  4  1  0
 13 15  1  6
  7 13  1  0
  2  1  2  3
  8 10  1  0
 15 16  2  0
  8  7  1  0
 15 17  1  0
  7 32  1  1
 11 12  1  0
 18 46  1  1
 21 23  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 10 36  1  0
 10 37  1  0
  6 30  1  0
  6 31  1  0
  5 28  1  0
  5 29  1  0
 23 52  1  0
 23 53  1  0
 20 49  1  0
 20 50  1  0
 19 47  1  0
 19 48  1  0
  3 26  1  0
  3 27  1  0
 22 51  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
  1 24  1  0
  1 25  1  0
 17 45  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       0.758   4.847   0.352  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.077   3.562   0.557  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.639   2.748   1.751  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.204   1.319   1.465  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.495   0.614   2.793  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.845  -0.861   2.637  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.701  -1.616   1.937  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.462  -1.069   0.481  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.623  -1.402  -0.481  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.825  -1.758  -0.074  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.815  -3.282   0.026  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.544  -3.762   1.446  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.750  -3.180   2.072  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.753  -3.609   3.559  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.026  -3.795   1.492  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.165  -3.384   1.651  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.835  -4.931   0.797  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.200   0.501   0.568  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.053   1.194  -0.803  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.142   1.961  -1.382  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.956   2.695  -0.315  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.009   3.423  -0.911  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.485   1.690   0.702  0.00  0.00           C+0
HETATM   24  H   UNK     0       0.127   5.391   1.048  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.110   5.378  -0.528  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.090   3.172   2.658  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.449   2.744   1.870  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.615   0.696   3.446  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.311   1.119   3.324  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.791  -0.958   2.096  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.019  -1.260   3.641  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.205  -1.333   2.500  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.700  -2.471  -0.692  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.596  -1.103  -0.093  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.488  -0.928  -1.457  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.702  -1.389   0.474  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.987  -1.495  -1.125  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.083  -3.709  -0.667  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.791  -3.664  -0.298  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.403  -3.474   2.068  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.530  -4.859   1.454  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.058  -3.127   4.116  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.698  -3.371   4.058  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.621  -4.694   3.653  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.740  -5.198   0.532  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.765   0.573   1.097  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.869   1.916  -0.659  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.432   0.501  -1.558  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.785   2.670  -2.142  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.801   1.274  -1.927  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.362   4.021  -0.230  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.230   2.158   1.362  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.000   0.856   0.226  0.00  0.00           H+0
CONECT    1    2   24   25                                                  
CONECT    2   21    3    1                                                  
CONECT    3    4    2   26   27                                             
CONECT    4   23    3    5   18                                             
CONECT    5    6    4   28   29                                             
CONECT    6    7    5   30   31                                             
CONECT    7    6   13    8   32                                             
CONECT    8   18    9   10    7                                             
CONECT    9    8   33   34   35                                             
CONECT   10   11    8   36   37                                             
CONECT   11   10   12   38   39                                             
CONECT   12   13   11   40   41                                             
CONECT   13   12   14   15    7                                             
CONECT   14   13   42   43   44                                             
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   45                                                       
CONECT   18   19    8    4   46                                             
CONECT   19   18   20   47   48                                             
CONECT   20   21   19   49   50                                             
CONECT   21   20    2   22   23                                             
CONECT   22   21   51                                                       
CONECT   23    4   21   52   53                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    9                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   22                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  112    0
END

RDKit          3D

53 56  0  0  0  0  0  0  0  0999 V2000
    0.7577    4.8470    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773    3.5623    0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392    2.7483    1.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042    1.3192    1.4652 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4946    0.6138    2.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455   -0.8608    2.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011   -1.6160    1.9372 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4616   -1.0688    0.4807 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6233   -1.4024   -0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8249   -1.7582   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8147   -3.2818    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439   -3.7623    1.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502   -3.1803    2.0718 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7529   -3.6094    3.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259   -3.7946    1.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1649   -3.3843    1.6507 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8349   -4.9312    0.7973 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002    0.5014    0.5681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0528    1.1939   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1421    1.9614   -1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556    2.6951   -0.3153 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0092    3.4231   -0.9110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853    1.6897    0.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1273    5.3911    1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103    5.3781   -0.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0897    3.1721    2.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4492    2.7441    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151    0.6960    3.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114    1.1191    3.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906   -0.9577    2.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0192   -1.2605    3.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2048   -1.3327    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7004   -2.4709   -0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961   -1.1030   -0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878   -0.9281   -1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7021   -1.3891    0.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873   -1.4949   -1.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -3.7087   -0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7905   -3.6641   -0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4032   -3.4742    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5300   -4.8594    1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0576   -3.1266    4.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6980   -3.3710    4.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6211   -4.6945    3.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7402   -5.1980    0.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7646    0.5732    1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688    1.9164   -0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323    0.5011   -1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853    2.6695   -2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8014    1.2741   -1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618    4.0207   -0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2301    2.1579    1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9998    0.8561    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 18 19  1  0
  4 23  1  0
 21 20  1  0
 20 19  1  0
 12 13  1  0
  4  3  1  1
  8 18  1  0
 21  2  1  0
  2  3  1  0
  7  6  1  0
 21 22  1  6
  6  5  1  0
  8  9  1  6
  5  4  1  0
 13 14  1  0
 18  4  1  0
 13 15  1  6
  7 13  1  0
  2  1  2  3
  8 10  1  0
 15 16  2  0
  8  7  1  0
 15 17  1  0
  7 32  1  1
 11 12  1  0
 18 46  1  1
 21 23  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 10 36  1  0
 10 37  1  0
  6 30  1  0
  6 31  1  0
  5 28  1  0
  5 29  1  0
 23 52  1  0
 23 53  1  0
 20 49  1  0
 20 50  1  0
 19 47  1  0
 19 48  1  0
  3 26  1  0
  3 27  1  0
 22 51  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
  1 24  1  0
  1 25  1  0
 17 45  1  0
M  END

View in JSmol

Synonyms

Value	Source
(-)-Steviol	ChEBI
(14-alpha)-13-Hydroxykaur-16-en-18-Oic acid	ChEBI
Hydroxydehydrostevic acid	ChEBI
(14-a)-13-Hydroxykaur-16-en-18-Oate	Generator
(14-a)-13-Hydroxykaur-16-en-18-Oic acid	Generator
(14-alpha)-13-Hydroxykaur-16-en-18-Oate	Generator
(14-Α)-13-hydroxykaur-16-en-18-Oate	Generator
(14-Α)-13-hydroxykaur-16-en-18-Oic acid	Generator
Hydroxydehydrostevate	Generator
Steviol, 3H-labeled	MeSH
Steviol, (+,-)-isomer	MeSH

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4570 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

(1R,4S,5R,9S,10R,13S)-13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

Traditional Name

(1R,4S,5R,9S,10R,13S)-13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@@]4(O[H])C(=C([H])[H])C([H])([H])[C@@]3(C4([H])[H])C([H])([H])C([H])([H])[C@]12[H]

InChI Identifier

InChI=1S/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)/t14-,15-,17+,18+,19+,20-/m0/s1

InChI Key

QFVOYBUQQBFCRH-VQSWZGCSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Bruguiera gymnorhiza	LOTUS Database	35616633
Bruguiera gymnorhiza L.	KNApSAcK Database	22123792
Ceriops decandra	LOTUS Database	35616633
Cucurbita maxima	KNApSAcK Database	22123792
Stevia rebaudiana	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	464.00 to 465.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	4.36 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.035 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	3.18	ALOGPS
logP	3.65	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-0.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.89 m³·mol⁻¹	ChemAxon
Polarizability	36.01 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

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Steviol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

145024

Good Scents ID

rw1014791

References

General References

Younes M, Aquilina G, Castle L, Engel KH, Fowler P, Frutos Fernandez MJ, Furst P, Gurtler R, Gundert-Remy U, Husoy T, Manco M, Mennes W, Passamonti S, Moldeus P, Shah R, Waalkens-Berendsen I, Wolfle D, Wright M, Barat Baviera JM, Degen G, Leblanc JC, Herman L, Giarola A, Aguilera J, Vianello G, Castle L: Safety evaluation of steviol glycoside preparations, including rebaudioside AM, obtained by enzymatic bioconversion of highly purified stevioside and/or rebaudioside A stevia leaf extracts. EFSA J. 2021 Aug 3;19(8):e06691. doi: 10.2903/j.efsa.2021.6691. eCollection 2021 Aug. [PubMed:34377189 ]
Zhu Y, Ding Y, Tian D, Li Y, Zhuang L, Wang Y, Xiao W, Zhu J: Theoretical design and preparation research of molecularly imprinted polymers for steviol glycosides. J Mol Model. 2021 Aug 7;27(9):238. doi: 10.1007/s00894-021-04819-9. [PubMed:34363125 ]
Li Y, Zhu W, Cai J, Liu W, Akihisa T, Li W, Kikuchi T, Xu J, Feng F, Zhang J: The role of metabolites of steviol glycosides and their glucosylated derivatives against diabetes-related metabolic disorders. Food Funct. 2021 Jul 28. doi: 10.1039/d1fo01370j. [PubMed:34319319 ]
Sheikhalipour M, Esmaielpour B, Gohari G, Haghighi M, Jafari H, Farhadi H, Kulak M, Kalisz A: Salt Stress Mitigation via the Foliar Application of Chitosan-Functionalized Selenium and Anatase Titanium Dioxide Nanoparticles in Stevia (Stevia rebaudiana Bertoni). Molecules. 2021 Jul 5;26(13). pii: molecules26134090. doi: 10.3390/molecules26134090. [PubMed:34279430 ]
Schade F, Schwack W, Demirbas Y, Morlock GE: Open-source all-in-one LabToGo Office Chromatography. Anal Chim Acta. 2021 Aug 22;1174:338702. doi: 10.1016/j.aca.2021.338702. Epub 2021 Jun 4. [PubMed:34247737 ]
Zhou X, Gong M, Lv X, Liu Y, Li J, Du G, Liu L: Metabolic engineering for the synthesis of steviol glycosides: current status and future prospects. Appl Microbiol Biotechnol. 2021 Jul;105(13):5367-5381. doi: 10.1007/s00253-021-11419-3. Epub 2021 Jul 1. [PubMed:34196745 ]
Zerva A, Chorozian K, Kritikou AS, Thomaidis NS, Topakas E: beta-Glucosidase and beta-Galactosidase-Mediated Transglycosylation of Steviol Glycosides Utilizing Industrial Byproducts. Front Bioeng Biotechnol. 2021 Jun 9;9:685099. doi: 10.3389/fbioe.2021.685099. eCollection 2021. [PubMed:34178968 ]
Park JM, Lee JH, Koh JH, Kim JM: Pretreatment methods for analyzing steviol glycosides in diverse food samples. J Food Sci. 2021 Jul;86(7):3075-3081. doi: 10.1111/1750-3841.15781. Epub 2021 Jun 22. [PubMed:34155649 ]
Sun Y, Xu X, Zhang T, Yang Y, Tong H, Yuan H: Comparative transcriptome analysis provides insights into steviol glycoside synthesis in stevia (Stevia rebaudiana Bertoni) leaves under nitrogen deficiency. Plant Cell Rep. 2021 Sep;40(9):1709-1722. doi: 10.1007/s00299-021-02733-1. Epub 2021 Jun 15. [PubMed:34129077 ]
Rengasamy N, Othman RY, Che HS, Harikrishna JA: Beyond the PAR spectra: impact of light quality on the germination, flowering, and metabolite content of Stevia rebaudiana (Bertoni). J Sci Food Agric. 2021 Jun 6. doi: 10.1002/jsfa.11359. [PubMed:34091912 ]
Yang, L.M. et al. (2007). Yang, L.M. et al, Phytochemistry 68, 562(2007). Phytochem..

Showing NP-Card for steviol (NP0030224)

MOL for NP0030224 (steviol)

3D MOL for NP0030224 (steviol)

3D SDF for NP0030224 (steviol)

3D-SDF for NP0030224 (steviol)

PDB for NP0030224 (steviol)

3D PDB for NP0030224 (steviol)

SMILES for NP0030224 (steviol)

INCHI for NP0030224 (steviol)

Structure for NP0030224 (steviol)

3D Structure for NP0030224 (steviol)