NP-MRD: Showing NP-Card for Gibberellin A4 (NP0014579)

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Record Information

Version

1.0

Created at

2021-01-05 23:42:37 UTC

Updated at

2021-07-15 17:17:40 UTC

NP-MRD ID

NP0014579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A4

Provided By

NPAtlas

Description

Gibberellin A4 is found in Dioscorea oppositifolia, Elsinoe menthae, Fusarium fujikuroi and Trachyspermum ammi . It was first documented in 2015 (PMID: 26281194). Based on a literature review very few articles have been published on Gibberellin A4 (PMID: 34299210) (PMID: 33064769) (PMID: 32919099) (PMID: 32869314) (PMID: 32452544) (PMID: 32333787).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120043D          

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     RDKit          3D

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 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  6  2  1  0  0  0  0
 10 19  1  6  0  0  0
  9  4  1  0  0  0  0
 20 10  1  0  0  0  0
 21  4  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
  6 31  1  6  0  0  0
  7 32  1  0  0  0  0
  7 33  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  9 36  1  1  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 13 41  1  6  0  0  0
 14 42  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
 20 46  1  1  0  0  0
 21 47  1  6  0  0  0
 24 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0014579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1([H])[C@@]2([H])[C@]3(OC(=O)[C@]2(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C3([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@@]3([H])C(=C([H])[H])C([H])([H])[C@@]12C3([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O5/c1-9-7-18-8-10(9)3-4-11(18)19-6-5-12(20)17(2,16(23)24-19)14(19)13(18)15(21)22/h10-14,20H,1,3-8H2,2H3,(H,21,22)/t10-,11-,12+,13-,14-,17-,18+,19-/m1/s1

> <INCHI_KEY>
RSQSQJNRHICNNH-WTVOOMFRSA-N

> <FORMULA>
C19H24O5

> <MOLECULAR_WEIGHT>
332.396

> <EXACT_MASS>
332.162373873

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.576654715847305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5R,8R,9S,10R,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.5603197853333337

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.445587590324653

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.288334110545963

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0419589762960797

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
84.07879999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,8R,9S,10R,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
    4.5537   -0.8267    0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4293   -0.6421    0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1372   -1.4081    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1414   -0.4723   -0.2346 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8876    0.0077   -1.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2177    0.3875   -0.8765 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0068    1.7262   -0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709    1.9630    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8460    0.7190    0.6164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6155    0.9286    0.4408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3135    1.5411    1.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6951    0.9441    1.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    0.7317    0.3656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5688    0.1492    0.5300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -0.0761   -0.5490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1304   -1.2070   -1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392    0.9022   -1.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441    1.0667   -2.7198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725    1.5685   -0.7775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -0.4672    0.2389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1634   -1.1180   -0.6104 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1470   -2.5766   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -3.3046   -1.4994 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115   -3.1778    0.7307 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4085   -0.2165    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6284   -1.5915    1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605   -1.6408    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318   -2.2947   -0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9612   -0.8300   -2.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3804    0.8869   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305    0.4164   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7111    1.8682    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736    2.5050   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5546    2.6854    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794    2.4300   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    0.4826    1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    2.6430    1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    1.3332    2.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7389    0.0549    2.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3404    1.7175    2.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5189    1.7701   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2805    0.6160   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2362   -1.0857   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9297   -1.1694   -2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -2.2098   -0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4309   -0.9725    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3748   -0.8387   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -3.9187    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  6  2  1  0
 10 19  1  6
  9  4  1  0
 20 10  1  0
 21  4  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  1
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  6
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 20 46  1  1
 21 47  1  6
 24 48  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       4.554  -0.827   0.844  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.429  -0.642   0.188  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.137  -1.408   0.359  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.141  -0.472  -0.235  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.888   0.008  -1.487  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.218   0.388  -0.877  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.007   1.726  -0.181  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.571   1.963   0.181  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.846   0.719   0.616  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.616   0.929   0.441  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.313   1.541   1.607  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.695   0.944   1.734  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.335   0.732   0.366  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.569   0.149   0.530  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.451  -0.076  -0.549  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.130  -1.207  -1.221  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.839   0.902  -1.519  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.144   1.067  -2.720  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.873   1.569  -0.778  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.223  -0.467   0.239  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.163  -1.118  -0.610  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.147  -2.577  -0.496  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.365  -3.305  -1.499  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.112  -3.178   0.731  0.00  0.00           O+0
HETATM   25  H   UNK     0       5.409  -0.217   0.633  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.628  -1.591   1.599  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.960  -1.641   1.419  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.232  -2.295  -0.287  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.961  -0.830  -2.199  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.380   0.887  -1.911  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.030   0.416  -1.600  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.711   1.868   0.654  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.274   2.505  -0.952  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.555   2.685   1.031  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.979   2.430  -0.638  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.131   0.483   1.670  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.417   2.643   1.498  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.748   1.333   2.551  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.739   0.055   2.361  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.340   1.718   2.239  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.519   1.770  -0.030  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.281   0.616  -0.013  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.236  -1.086  -1.114  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.930  -1.169  -2.321  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.803  -2.210  -0.847  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.431  -0.973   1.177  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.375  -0.839  -1.662  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.473  -3.919   1.077  0.00  0.00           H+0
CONECT    1    2   25   26                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    4   27   28                                             
CONECT    4    3    5    9   21                                             
CONECT    5    4    6   29   30                                             
CONECT    6    5    7    2   31                                             
CONECT    7    6    8   32   33                                             
CONECT    8    7    9   34   35                                             
CONECT    9    8   10    4   36                                             
CONECT   10    9   11   19   20                                             
CONECT   11   10   12   37   38                                             
CONECT   12   11   13   39   40                                             
CONECT   13   12   14   15   41                                             
CONECT   14   13   42                                                       
CONECT   15   13   16   17   20                                             
CONECT   16   15   43   44   45                                             
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10                                                       
CONECT   20   15   21   10   46                                             
CONECT   21   20   22    4   47                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   48                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    5                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   24                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  104    0
END

RDKit          3D

48 52  0  0  0  0  0  0  0  0999 V2000
    4.5537   -0.8267    0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4293   -0.6421    0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1372   -1.4081    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1414   -0.4723   -0.2346 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8876    0.0077   -1.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2177    0.3875   -0.8765 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0068    1.7262   -0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709    1.9630    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8460    0.7190    0.6164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6155    0.9286    0.4408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3135    1.5411    1.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6951    0.9441    1.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    0.7317    0.3656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5688    0.1492    0.5300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -0.0761   -0.5490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1304   -1.2070   -1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392    0.9022   -1.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441    1.0667   -2.7198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725    1.5685   -0.7775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -0.4672    0.2389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1634   -1.1180   -0.6104 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1470   -2.5766   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -3.3046   -1.4994 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115   -3.1778    0.7307 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4085   -0.2165    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6284   -1.5915    1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605   -1.6408    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318   -2.2947   -0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9612   -0.8300   -2.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3804    0.8869   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305    0.4164   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7111    1.8682    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736    2.5050   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5546    2.6854    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794    2.4300   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    0.4826    1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    2.6430    1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    1.3332    2.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7389    0.0549    2.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3404    1.7175    2.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5189    1.7701   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2805    0.6160   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2362   -1.0857   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9297   -1.1694   -2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -2.2098   -0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4309   -0.9725    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3748   -0.8387   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -3.9187    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  6  2  1  0
 10 19  1  6
  9  4  1  0
 20 10  1  0
 21  4  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  1
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  6
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 20 46  1  1
 21 47  1  6
 24 48  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1R,2R,5R,8R,9S,10R,12S)-12-Hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1,.0,.0,]heptadecane-9-carboxylate	Generator

Chemical Formula

C₁₉H₂₄O₅

Average Mass

332.3960 Da

Monoisotopic Mass

332.16237 Da

IUPAC Name

(1R,2R,5R,8R,9S,10R,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

Traditional Name

(1R,2R,5R,8R,9S,10R,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12[C@H]3[C@H](C(O)=O)[C@@]45C[C@@H](CC[C@H]4[C@@]3(CC[C@@H]1O)OC2=O)C(=C)C5

InChI Identifier

InChI=1S/C19H24O5/c1-9-7-18-8-10(9)3-4-11(18)19-6-5-12(20)17(2,16(23)24-19)14(19)13(18)15(21)22/h10-14,20H,1,3-8H2,2H3,(H,21,22)/t10-,11-,12+,13-,14-,17?,18+,19-/m1/s1

InChI Key

RSQSQJNRHICNNH-WTVOOMFRSA-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
Abelmoschus esculentus	KNApSAcK Database	22123792
Allium cepa	KNApSAcK Database	22123792
Alstroemeria hybrida	KNApSAcK Database	22123792
Arabidopsis thaliana	KNApSAcK Database	22123792
Aralia cordata	KNApSAcK Database	22123792
Begonia x cheimantha	KNApSAcK Database	22123792
Brassica napus	KNApSAcK Database	22123792
Calystegia soldanella	KNApSAcK Database	22123792
Castanea henryi	KNApSAcK Database	22123792
Cibotium glaucum	KNApSAcK Database	22123792
Citrus reticulata	KNApSAcK Database	22123792
Citrus sinensis	KNApSAcK Database	22123792
Citrus unshiu	KNApSAcK Database	22123792
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	KNAPSACK
Cucumis melo	KNApSAcK Database	22123792
Cucumis sativus	KNApSAcK Database	22123792
Cucumis sativus L.	FooDB	KNAPSACK
Cucurbita maxima	KNApSAcK Database	22123792
Cyathea australis	KNApSAcK Database	22123792
Dalbergia dolichopetala	KNApSAcK Database	22123792
Daucus carota	KNApSAcK Database	22123792
Daucus carota ssp. sativus	FooDB	KNAPSACK
Dicksonia antarctica	KNApSAcK Database	22123792
Dioscorea oppositifolia	LOTUS Database	35616633
Dioscorea polystachya	KNApSAcK Database	22123792
Elsinoe menthae	LOTUS Database	35616633
Eucalyptus globulus	KNApSAcK Database	22123792
Fusarium fujikuroi	NPAtlas	26281194
Gossypium hirsutum	KNApSAcK Database	22123792
Helianthus annuus	KNApSAcK Database	22123792
Helianthus annuus L.	FooDB	KNAPSACK
Juglans regia	KNApSAcK Database	22123792
Lilium elegans	KNApSAcK Database	22123792
Litchi chinensis	KNApSAcK Database	22123792
Lupinus albus	KNApSAcK Database	22123792
Malva sylvestris	KNApSAcK Database	22123792
Marah macrocarpus	KNApSAcK Database	22123792
Matthiola incana	KNApSAcK Database	22123792
Ornithogalum thyrsoides	KNApSAcK Database	22123792
Orobanche minor	KNApSAcK Database	22123792
Oryza sativa	KNApSAcK Database	22123792
Phaseolus coccineus	KNApSAcK Database	22123792
Phaseolus vulgaris	KNApSAcK Database	22123792
Picea abies	KNApSAcK Database	22123792
Picea sitchensis	KNApSAcK Database	22123792
Pimpinella anisum	KNApSAcK Database	22123792
Pinus attenuata	KNApSAcK Database	22123792
Pinus sylvestris	KNApSAcK Database	22123792
Pisum sativum	KNApSAcK Database	22123792
Pseudotsuga menziesii	KNApSAcK Database	22123792
Pyrus malus	KNApSAcK Database	22123792
Raphanus sativus	KNApSAcK Database	22123792
Rumex acetosa	KNApSAcK Database	22123792
Rumex palustris	KNApSAcK Database	22123792
Saccharum spp.	KNApSAcK Database	22123792
Sechium edule	KNApSAcK Database	22123792
Senna tora	KNApSAcK Database	22123792
Solanum lycopersicum	KNApSAcK Database	22123792
Solanum lycopersicum var. lycopersicum	FooDB	KNAPSACK
Spinacia oleracea	KNApSAcK Database	22123792
Taiwania cryptomerioides	KNApSAcK Database	22123792
Trachyspermum ammi	-	KNApSAcK
Trifolium repens	KNApSAcK Database	22123792
Triticum aestivum	KNApSAcK Database	22123792
Zea mays	KNApSAcK Database	22123792
Zea mays L.	FooDB	KNAPSACK

Species Where Detected

Species Name	Source	Reference
Bacillus licheniformis	KNApSAcK Database	22123792
Bacillus pumilus	KNApSAcK Database	22123792
Gibberella fujikuroi	KNApSAcK Database	22123792
Phaeosphaeria sp. L489	KNApSAcK Database	22123792
Rhizobium phaseoli	KNApSAcK Database	22123792
Sphaceloma bidentis	KNApSAcK Database	22123792
Sphaceloma manihoticola	KNApSAcK Database	22123792
Sphaceloma menthae	KNApSAcK Database	22123792
Sphaceloma perseae	KNApSAcK Database	22123792
Sphaceloma rhois	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	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.38	ALOGPS
logP	1.56	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.08 m³·mol⁻¹	ChemAxon
Polarizability	34.58 Å³	ChemAxon
Number of Rings	5	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

NPAtlas ID

NPA001469

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000004

Chemspider ID

391671

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gibberellin

METLIN ID

Not Available

PubChem Compound

443457

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Krasnova TN, Samokhodskaya LM, Ivanitsky LV, Korogodina AD, Borisov EN, Nikiforova NV, Novikov PI, Kamalov AA, Mukhin NA: [Impact of interleukin-10 and interleukin-28 gene polymorphisms on the development and course of lupus nephritis]. Ter Arkh. 2015;87(6):40-44. doi: 10.17116/terarkh201587640-44. [PubMed:26281194 ]
Kongdin M, Mahong B, Lee SK, Shim SH, Jeon JS, Ketudat Cairns JR: Action of Multiple Rice beta-Glucosidases on Abscisic Acid Glucose Ester. Int J Mol Sci. 2021 Jul 15;22(14). pii: ijms22147593. doi: 10.3390/ijms22147593. [PubMed:34299210 ]
Pons S, Fournier S, Chervin C, Becard G, Rochange S, Frei Dit Frey N, Puech Pages V: Phytohormone production by the arbuscular mycorrhizal fungus Rhizophagus irregularis. PLoS One. 2020 Oct 16;15(10):e0240886. doi: 10.1371/journal.pone.0240886. eCollection 2020. [PubMed:33064769 ]
Acosta-Motos JR, Rothwell SA, Massam MJ, Albacete A, Zhang H, Dodd IC: Alternate wetting and drying irrigation increases water and phosphorus use efficiency independent of substrate phosphorus status of vegetative rice plants. Plant Physiol Biochem. 2020 Oct;155:914-926. doi: 10.1016/j.plaphy.2020.06.017. Epub 2020 Jun 13. [PubMed:32919099 ]
Arshad M, Chaudhary AR, Mumtaz MW, Raza SA, Ahmad M, Mukhtar H, Bashir R: Polyphenol fingerprinting and hypoglycemic attributes of optimized Cycas circinalis leaf extracts. J Sci Food Agric. 2021 Mar 15;101(4):1530-1537. doi: 10.1002/jsfa.10771. Epub 2020 Sep 18. [PubMed:32869314 ]
Pichler G, Stoggl W, Candotto Carniel F, Muggia L, Ametrano CG, Holzinger A, Tretiach M, Kranner I: Abundance and Extracellular Release of Phytohormones in Aero-terrestrial Microalgae (Trebouxiophyceae, Chlorophyta) As a Potential Chemical Signaling Source(1). J Phycol. 2020 Oct;56(5):1295-1307. doi: 10.1111/jpy.13032. Epub 2020 Jul 3. [PubMed:32452544 ]
Okada K, Wada M, Takebayashi Y, Kojima M, Sakakibara H, Nakayasu M, Mizutani M, Nakajima M, Moriya S, Shimizu T, Abe K: Columnar growth phenotype in apple results from gibberellin deficiency by ectopic expression of a dioxygenase gene. Tree Physiol. 2020 Aug 29;40(9):1205-1216. doi: 10.1093/treephys/tpaa049. [PubMed:32333787 ]
Manoharlal R, Saiprasad GVS: Assessment of germination, phytochemicals, and transcriptional responses to ethephon priming in soybean [Glycine max (L.) Merrill]. Genome. 2019 Dec;62(12):769-783. doi: 10.1139/gen-2019-0013. Epub 2019 Sep 3. [PubMed:31479624 ]
Zhang X, Goatley M, Wu W, Ervin E, Shang C: Drought-induced injury is associated with hormonal alteration in Kentucky bluegrass. Plant Signal Behav. 2019;14(10):e1651607. doi: 10.1080/15592324.2019.1651607. Epub 2019 Aug 12. [PubMed:31403391 ]
Rizza A, Walia A, Tang B, Jones AM: Visualizing Cellular Gibberellin Levels Using the nlsGPS1 Forster Resonance Energy Transfer (FRET) Biosensor. J Vis Exp. 2019 Jan 12;(143). doi: 10.3791/58739. [PubMed:30688303 ]
Ju Y, Feng L, Wu J, Ye Y, Zheng T, Cai M, Cheng T, Wang J, Zhang Q, Pan H: Transcriptome analysis of the genes regulating phytohormone and cellular patterning in Lagerstroemia plant architecture. Sci Rep. 2018 Oct 11;8(1):15162. doi: 10.1038/s41598-018-33506-8. [PubMed:30310123 ]
Li ZF, Guo Y, Ou L, Hong H, Wang J, Liu ZX, Guo B, Zhang L, Qiu L: Identification of the dwarf gene GmDW1 in soybean (Glycine max L.) by combining mapping-by-sequencing and linkage analysis. Theor Appl Genet. 2018 May;131(5):1001-1016. doi: 10.1007/s00122-017-3044-8. Epub 2018 Mar 17. [PubMed:29550969 ]
Suh JH, Han SB, Wang Y: Development of an improved sample preparation platform for acidic endogenous hormones in plant tissues using electromembrane extraction. J Chromatogr A. 2018 Feb 2;1535:1-8. doi: 10.1016/j.chroma.2017.12.068. Epub 2017 Dec 30. [PubMed:29306633 ]

Showing NP-Card for Gibberellin A4 (NP0014579)

MOL for NP0014579 (Gibberellin A4)

3D MOL for NP0014579 (Gibberellin A4)

3D SDF for NP0014579 (Gibberellin A4)

3D-SDF for NP0014579 (Gibberellin A4)

PDB for NP0014579 (Gibberellin A4)

3D PDB for NP0014579 (Gibberellin A4)

SMILES for NP0014579 (Gibberellin A4)

INCHI for NP0014579 (Gibberellin A4)

Structure for NP0014579 (Gibberellin A4)

3D Structure for NP0014579 (Gibberellin A4)