NP-MRD: Showing NP-Card for Gibberellic acid (NP0002697)

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Record Information

Version

2.0

Created at

2020-11-23 19:38:12 UTC

Updated at

2021-08-19 23:59:15 UTC

NP-MRD ID

NP0002697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellic acid

Provided By

BMRB

Description

Gibberellin A3, also known as GA3 or gibberellic acid, belongs to the class of organic compounds known as c19-gibberellin 6-carboxylic acids. These are c19-gibberellins with a carboxyl group at the 6-position. Thus, gibberellin A3 is considered to be an isoprenoid. Gibberellin A3 exists in all living organisms, ranging from bacteria to humans. Gibberellin A3 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. Gibberellic acid is found in Alcea rosea, Avena sativa , Azospirillum brasilense, Azospirillum lipoferum, Brassica rapa, Brassica campestris , Bruguiera gymnorrhiza , Carica papaya , Citrus sinensis , Cucumis sativus , Ipomoea aquatica, Ipomoea purpurea, Marah macrocarpa, Mus musculus, Cenchrus americanus and Vitis vinifera . Gibberellic acid was first documented in 1986 (PMID: 3460143). Based on a literature review a small amount of articles have been published on Gibberellin A3 (PMID: 17984079) (PMID: 18948165) (PMID: 19815399) (PMID: 21216576).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 47 51  0  0  0  0  0  0  0  0999 V2000
   -4.6382    1.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3076    0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9653    1.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9138    0.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4110    0.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388   -1.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7360   -1.0498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5693   -2.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -2.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443   -1.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -1.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7933   -0.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    0.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6482    0.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755   -1.1161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9701    0.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625    1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3
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M  END

NP0002697
     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
   -3.9492    0.7916    1.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0069    0.7390    1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6595    1.4214    1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031    0.5628    0.0584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9253    0.4337   -1.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1450   -0.0324   -0.2492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3209    0.2281   -0.9091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9768   -1.5172    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5199   -1.8731   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6503   -0.8046    0.6600 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7547   -1.0846    0.3142 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5380   -1.8528    1.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358   -1.6475    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887   -1.0468    0.1254 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7076   -0.4362    0.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6051   -0.1054   -0.6440 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.1094    1.4620   -1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


     RDKit          2D

 47 51  0  0  0  0  0  0  0  0999 V2000
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M  END
> <DATABASE_ID>
NP0002697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@@]3(C)[C@@H](O)C=C[C@@]21OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1

> <INCHI_KEY>
IXORZMNAPKEEDV-OBDJNFEBSA-N

> <FORMULA>
C19H22O6

> <MOLECULAR_WEIGHT>
346.3744

> <EXACT_MASS>
346.141638436

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.346316164986575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,8S,9S,10R,11R,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic acid

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.3509132836666674

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.06512209173422

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.163467082979854

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9049344149234976

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
86.4155

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8S,9S,10R,11R,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002697
     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
   -3.9492    0.7916    1.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0069    0.7390    1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6595    1.4214    1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031    0.5628    0.0584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9253    0.4337   -1.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1450   -0.0324   -0.2492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3209    0.2281   -0.9091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9768   -1.5172    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5199   -1.8731   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6503   -0.8046    0.6600 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7547   -1.0846    0.3142 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5380   -1.8528    1.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358   -1.6475    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887   -1.0468    0.1254 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7076   -0.4362    0.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6051   -0.1054   -0.6440 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3431    1.0649   -1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9117   -0.9061   -1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1927   -0.9351   -2.9067 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102   -1.5933   -1.0177 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602    0.2853    0.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4055    1.1202   -0.3781 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5685    2.5660   -0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4494    3.0781    0.5959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2807    3.4553   -0.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8274    1.3643    2.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8912    0.2703    1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215    2.4053    0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311    1.4277    2.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1094    1.4620   -1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6441   -0.2768   -1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4781   -0.4937   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860   -2.1144   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928   -1.8278    0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582   -2.0948   -1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3353   -2.8097    0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229   -0.8377    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0844   -2.5558    1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4554   -1.8925    2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7980   -1.9240   -0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4527   -1.1040    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613    1.4786   -0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6706    1.8790   -1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455    0.7779   -2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    0.6110    1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4681    0.9468   -1.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3481    3.3969   -1.8207 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  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  6  2  1  0
 11 20  1  6
 10  4  1  0
 21 11  1  0
 22  4  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  1
 12 38  1  0
 13 39  1  0
 14 40  1  6
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 21 45  1  1
 22 46  1  6
 25 47  1  0
M  END

HEADER    PROTEIN                                 21-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUL-20         0                                  
HETATM    1  C   UNK     0       0.262  -1.044   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.027   1.750   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.703   2.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.128   3.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.271   1.455   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.474   2.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.695   0.103   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.726   1.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.158   0.195   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.204   0.816   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0      -0.214  -0.007   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       0.739  -2.508   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.246  -2.827   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.733   3.653   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.290  -3.653   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.201   0.973   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.201  -0.567   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.201   2.506   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.542   1.740   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.542  -1.355   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.366  -0.134   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.870   0.973   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.870  -0.567   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.550  -2.881   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.237   0.043   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.204  -1.334   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0      -1.201  -2.101   0.000  0.00  0.00           H+0
CONECT    1    9   12   17                                                  
CONECT    2    9    6                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    9   11   16                                             
CONECT    6    4    8    2   14                                             
CONECT    7    8    9                                                       
CONECT    8    6    7   10                                                  
CONECT    9    5    7    2    1                                             
CONECT   10    8                                                            
CONECT   11    5                                                            
CONECT   12    1   13   15                                                  
CONECT   13   12                                                            
CONECT   14    6                                                            
CONECT   15   12                                                            
CONECT   16   17   18   19    5                                             
CONECT   17   16   20   27    1                                             
CONECT   18   16   21                                                       
CONECT   19   16   22                                                       
CONECT   20   17   23   24   21                                             
CONECT   21   18   25   20                                                  
CONECT   22   19   23                                                       
CONECT   23   20   26   22                                                  
CONECT   24   20                                                            
CONECT   25   21                                                            
CONECT   26   23                                                            
CONECT   27   17                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

COMPND    NP0002697
HETATM    1  C1  UNL     1      -3.949   0.792   1.948  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.007   0.739   1.016  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.659   1.421   1.048  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.903   0.563   0.058  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.925   0.434  -1.052  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.145  -0.032  -0.249  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.321   0.228  -0.909  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.977  -1.517   0.022  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.520  -1.873  -0.017  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.650  -0.805   0.660  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.755  -1.085   0.314  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.538  -1.853   1.288  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.836  -1.648   1.319  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.489  -1.047   0.125  1.00  0.00           C  
HETATM   15  O2  UNL     1       4.708  -0.436   0.481  1.00  0.00           O  
HETATM   16  C14 UNL     1       2.605  -0.105  -0.644  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.343   1.065  -1.218  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.912  -0.906  -1.688  1.00  0.00           C  
HETATM   19  O3  UNL     1       2.193  -0.935  -2.907  1.00  0.00           O  
HETATM   20  O4  UNL     1       0.910  -1.593  -1.018  1.00  0.00           O  
HETATM   21  C17 UNL     1       1.460   0.285   0.242  1.00  0.00           C  
HETATM   22  C18 UNL     1       0.405   1.120  -0.378  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.568   2.566  -0.157  1.00  0.00           C  
HETATM   24  O5  UNL     1       1.449   3.078   0.596  1.00  0.00           O  
HETATM   25  O6  UNL     1      -0.281   3.455  -0.799  1.00  0.00           O  
HETATM   26  H1  UNL     1      -3.827   1.364   2.870  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.891   0.270   1.846  1.00  0.00           H  
HETATM   28  H3  UNL     1      -1.821   2.405   0.593  1.00  0.00           H  
HETATM   29  H4  UNL     1      -1.231   1.428   2.049  1.00  0.00           H  
HETATM   30  H5  UNL     1      -2.109   1.462  -1.432  1.00  0.00           H  
HETATM   31  H6  UNL     1      -1.644  -0.277  -1.830  1.00  0.00           H  
HETATM   32  H7  UNL     1      -4.478  -0.494  -1.562  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.486  -2.114  -0.768  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.393  -1.828   0.989  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.158  -2.095  -1.042  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.335  -2.810   0.571  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.823  -0.838   1.739  1.00  0.00           H  
HETATM   38  H13 UNL     1       1.084  -2.556   1.952  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.455  -1.893   2.167  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.798  -1.924  -0.517  1.00  0.00           H  
HETATM   41  H16 UNL     1       5.453  -1.104   0.498  1.00  0.00           H  
HETATM   42  H17 UNL     1       4.061   1.479  -0.485  1.00  0.00           H  
HETATM   43  H18 UNL     1       2.671   1.879  -1.547  1.00  0.00           H  
HETATM   44  H19 UNL     1       3.946   0.778  -2.107  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.777   0.611   1.249  1.00  0.00           H  
HETATM   46  H21 UNL     1       0.468   0.947  -1.494  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.348   3.397  -1.821  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3    6
CONECT    3    4   28   29
CONECT    4    5   10   22
CONECT    5    6   30   31
CONECT    6    7    8
CONECT    7   32
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   37
CONECT   11   12   20   21
CONECT   12   13   13   38
CONECT   13   14   39
CONECT   14   15   16   40
CONECT   15   41
CONECT   16   17   18   21
CONECT   17   42   43   44
CONECT   18   19   19   20
CONECT   21   22   45
CONECT   22   23   46
CONECT   23   24   24   25
CONECT   25   47
END

NP0002697
     RDKit          3D

47 51  0  0  0  0  0  0  0  0999 V2000
   -3.9492    0.7916    1.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0069    0.7390    1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6595    1.4214    1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031    0.5628    0.0584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9253    0.4337   -1.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1450   -0.0324   -0.2492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3209    0.2281   -0.9091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9768   -1.5172    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5199   -1.8731   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6503   -0.8046    0.6600 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7547   -1.0846    0.3142 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5380   -1.8528    1.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358   -1.6475    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887   -1.0468    0.1254 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7076   -0.4362    0.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6051   -0.1054   -0.6440 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3431    1.0649   -1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9117   -0.9061   -1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1927   -0.9351   -2.9067 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102   -1.5933   -1.0177 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602    0.2853    0.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4055    1.1202   -0.3781 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5685    2.5660   -0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4494    3.0781    0.5959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2807    3.4553   -0.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8274    1.3643    2.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8912    0.2703    1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215    2.4053    0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311    1.4277    2.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1094    1.4620   -1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6441   -0.2768   -1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4781   -0.4937   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860   -2.1144   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928   -1.8278    0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582   -2.0948   -1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3353   -2.8097    0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229   -0.8377    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0844   -2.5558    1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4554   -1.8925    2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7980   -1.9240   -0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4527   -1.1040    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613    1.4786   -0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6706    1.8790   -1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455    0.7779   -2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    0.6110    1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4681    0.9468   -1.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3481    3.3969   -1.8207 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  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  6  2  1  0
 11 20  1  6
 10  4  1  0
 21 11  1  0
 22  4  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  1
 12 38  1  0
 13 39  1  0
 14 40  1  6
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 21 45  1  1
 22 46  1  6
 25 47  1  0
M  END

View in JSmol

Synonyms

Value	Source
(+)-Gibberellic acid	ChEBI
GA3	ChEBI
Gibberellic acid	ChEBI
Gibberellic acid ga3	ChEBI
Gibberellin	ChEBI
Gibberellin 3	ChEBI
Gibberellinsaeure	ChEBI
(+)-Gibberellate	Generator
Gibberellate	Generator
Gibberellate ga3	Generator
Gibberelate	HMDB
Gibberelic acid	HMDB
Gibberelin	HMDB
Gibberellins	HMDB
Gibberillate	HMDB
Gibberillic acid	HMDB
GA(3) gibberellin	HMDB
GA3 gibberellin	HMDB
(+)-Gibberellin a3	HMDB
GA	HMDB
Gibberellin ga3	HMDB
Gibberellin A3	MeSH

Chemical Formula

C₁₉H₂₂O₆

Average Mass

346.3744 Da

Monoisotopic Mass

346.14164 Da

IUPAC Name

(1R,2R,5S,8S,9S,10R,11R,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic acid

Traditional Name

(1R,2R,5S,8S,9S,10R,11R,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@@]3(C)[C@@H](O)C=C[C@@]21OC3=O

InChI Identifier

InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1

InChI Key

IXORZMNAPKEEDV-OBDJNFEBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	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
Abelmoschus esculentus	KNApSAcK Database	22123792
Alcea rosea	LOTUS Database	35616633
Althaea rosea	KNApSAcK Database	22123792
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arabidopsis thaliana	KNApSAcK Database	22123792
Avena sativa	KNApSAcK Database	22123792
Avena sativa L.	Plant	KNApSAcK
Azospirillum brasilense	-	KNApSAcK
Azospirillum lipoferum	-	KNApSAcK
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica campestris	KNApSAcK Database	22123792
Brassica napus	KNApSAcK Database	22123792
Brassica rapa	LOTUS Database	35616633
Brassica rapa subsp. oleifera	Plant	KNApSAcK
Bruguiera gymnorhiza	Plant	KNApSAcK
Bruguiera gymnorrhiza	KNApSAcK Database	22123792
Bubalus bubalis	FooDB	FooDB
Calystegia soldanella	KNApSAcK Database	22123792
Camellia sinensis	KNApSAcK Database	22123792
Capra aegagrus hircus	FooDB	FooDB
Carica papaya	KNApSAcK Database	22123792
Carica papaya L.	Plant	KNApSAcK
Carthamus tinctorius	KNApSAcK Database	22123792
Cassia fistula	KNApSAcK Database	22123792
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Citrus sinensis	KNApSAcK Database	22123792
Citrus X sinensis (L.) Osbeck (pro. sp.)	Plant	KNApSAcK
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Cucumis melo	KNApSAcK Database	22123792
Cucumis sativus	KNApSAcK Database	22123792
Cucumis sativus L.	Plant	KNApSAcK
Dalbergia dolichopetala	KNApSAcK Database	22123792
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Fragaria spp.	KNApSAcK Database	22123792
Fragaria x ananassa	KNApSAcK Database	22123792
Gallus gallus	FooDB	FooDB
Gossypium hirsutum	KNApSAcK Database	22123792
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hordeum vulgare	KNApSAcK Database	22123792
Ipomoea aquatica	LOTUS Database	35616633
Ipomoea batatas	KNApSAcK Database	22123792
Ipomoea purpurea	LOTUS Database	35616633
Ipomoea reptans	KNApSAcK Database	22123792
Ipomoea tricolor	KNApSAcK Database	22123792
Lactuca sativa	KNApSAcK Database	22123792
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Lolium temulentum	KNApSAcK Database	22123792
Lupinus albus	KNApSAcK Database	22123792
Malus domestica	KNApSAcK Database	22123792
Mangifera indica	KNApSAcK Database	22123792
Marah macrocarpa	LOTUS Database	35616633
Marah macrocarpus	KNApSAcK Database	22123792
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Pennisetum americanum	LOTUS Database	35616633
Pennisetum glaucum	KNApSAcK Database	22123792
Pharbitis purpurea	KNApSAcK Database	22123792
Phaseolus coccineus	KNApSAcK Database	22123792
Phaseolus lunatus	KNApSAcK Database	22123792
Phaseolus multiflorus	KNApSAcK Database	22123792
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Picea abies	KNApSAcK Database	22123792
Pinus attenuata	KNApSAcK Database	22123792
Pinus sylvestris	KNApSAcK Database	22123792
Pisum sativum	KNApSAcK Database	22123792
Prunus avium	KNApSAcK Database	22123792
Prunus cerasus	KNApSAcK Database	22123792
Prunus persica	KNApSAcK Database	22123792
Pseudotsuga menziesii	KNApSAcK Database	22123792
Pyrus communis	KNApSAcK Database	22123792
Quamoclit pennata	KNApSAcK Database	22123792
Rhizophora mucronata	KNApSAcK Database	22123792
Saccharum spp.	KNApSAcK Database	22123792
Secale cereale	KNApSAcK Database	22123792
Sechium edule	KNApSAcK Database	22123792
Senna tora	KNApSAcK Database	22123792
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sonneratia apetala	KNApSAcK Database	22123792
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Triticum aestivum	KNApSAcK Database	22123792
Vigna unguiculata	KNApSAcK Database	22123792
Vitis vinifera	KNApSAcK Database	22123792
Vitis vinifera L.	Plant	KNApSAcK
Zea mays	KNApSAcK Database	22123792
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Species Where Detected

Species Name	Source	Reference
Bacillus licheniformis	KNApSAcK Database	22123792
Bacillus pumilus	KNApSAcK Database	22123792
Fusarium fujikuroi	KNApSAcK Database	22123792
Gibberella fujikuroi	KNApSAcK Database	22123792
Gluconacetobacter diazotrophicus	KNApSAcK Database	22123792
Herbaspirillum seropedicae	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c19-gibberellin 6-carboxylic acids. These are c19-gibberellins with a carboxyl group at the 6-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C19-gibberellin 6-carboxylic acids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	234.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	Not Available	Not Available
Water Solubility	5000 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	0.240	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0.66	ALOGPS
logP	0.35	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-0.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.42 m³·mol⁻¹	ChemAxon
Polarizability	36.35 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

HMDB ID

HMDB0003559

DrugBank ID

DB07814

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Gibberellic_acid

METLIN ID

6954

PubChem Compound

6466

PDB ID

Not Available

ChEBI ID

28833

Good Scents ID

rw1133321

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Yamaki T, Takeda K: [A simple bioassay method of urinary indoleacetic acid, a cancer growth factor]. J UOEH. 1986 Mar 20;8 Suppl:297-302. [PubMed:3460143 ]
Erin N, Afacan B, Ersoy Y, Ercan F, Balci MK: Gibberellic acid, a plant growth regulator, increases mast cell recruitment and alters Substance P levels. Toxicology. 2008 Dec 5;254(1-2):75-81. doi: 10.1016/j.tox.2008.09.020. Epub 2008 Oct 2. [PubMed:18948165 ]
Troudi A, Mahjoubi Samet A, Zeghal N: Hepatotoxicity induced by gibberellic acid in adult rats and their progeny. Exp Toxicol Pathol. 2010 Nov;62(6):637-42. doi: 10.1016/j.etp.2009.08.010. Epub 2009 Oct 7. [PubMed:19815399 ]
Troudi A, Bouaziz H, Soudani N, Ben Amara I, Boudawara T, Touzani H, Lyoussi B, Zeghal N: Neurotoxicity and oxidative stress induced by gibberellic acid in rats during late pregnancy and early postnatal periods: biochemical and histological changes. Exp Toxicol Pathol. 2012 Sep;64(6):583-90. doi: 10.1016/j.etp.2010.11.017. Epub 2011 Jan 8. [PubMed:21216576 ]

Showing NP-Card for Gibberellic acid (NP0002697)

MOL for NP0002697 (Gibberellic acid)

3D MOL for NP0002697 (Gibberellic acid)

3D SDF for NP0002697 (Gibberellic acid)

3D-SDF for NP0002697 (Gibberellic acid)

PDB for NP0002697 (Gibberellic acid)

3D PDB for NP0002697 (Gibberellic acid)

SMILES for NP0002697 (Gibberellic acid)

INCHI for NP0002697 (Gibberellic acid)

Structure for NP0002697 (Gibberellic acid)

3D Structure for NP0002697 (Gibberellic acid)