NP-MRD: Showing NP-Card for (1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid (NP0204032)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 23:37:52 UTC

Updated at

2022-09-04 23:37:52 UTC

NP-MRD ID

NP0204032

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

Description

Gibberellin 1 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. (1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid is found in Arabidopsis thaliana and Prunus armeniaca. (1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid was first documented in 2015 (PMID: 26241499). Based on a literature review a small amount of articles have been published on Gibberellin 1 (PMID: 35643621) (PMID: 32345611) (PMID: 29441084).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201372D          

 25 29  0  0  1  0            999 V2000
    6.1457   -0.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4341   -1.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331   -0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -1.3568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6689   -1.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3493   -1.9378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1486   -2.1420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080   -2.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1559   -2.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6513   -2.1599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8111   -2.0778    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4387   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4841   -0.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7495   -0.2250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9062    0.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517   -0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4162    0.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6187   -1.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7941   -1.2175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0012   -1.9210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5867   -1.1491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3307   -0.8465    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4368   -0.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2009    0.7622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1983    0.2888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 11 20  1  6  0  0  0
 21 16  1  1  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
    3.4218    1.2396   -2.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8493    0.8336   -1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6338    1.4552   -0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191    0.3328    0.2422 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3660   -0.1989    0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705   -0.3060   -0.3341 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6009   -0.2811   -0.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453   -1.5797   -1.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4317   -1.9782   -0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5775   -0.7324   -0.6904 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8342   -0.9869   -0.2913 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7628   -1.3181   -1.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0099   -0.4844   -1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4925   -0.4936    0.1610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6071    0.3509    0.2701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079   -0.1014    1.1451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8804    0.8728    2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8807   -1.3617    1.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2184   -1.8710    2.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9509   -1.8564    0.8245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2198    0.3615    0.3418 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0041    0.6131    1.1719 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0276    1.9279    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0843    2.0506    3.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097    3.1368    1.1225 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    2.0699   -2.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2974    0.7130   -2.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398    1.7722   -1.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    2.3143   -0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -1.1510    1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120    0.5180    1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1390    0.3337   -0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -1.3830   -2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -2.4001   -0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0617   -2.6206   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3527   -2.5630    0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -0.3654   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1009   -2.3924   -1.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846   -1.1082   -2.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219   -0.9717   -1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9067    0.5343   -1.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8765   -1.5238    0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9945    0.4549   -0.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6741    1.9207    1.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0072    0.8006    2.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5444    0.6641    3.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4385    1.1210   -0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -0.1669    1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    3.8047    1.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  1
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 25  1  0
 23 24  2  0
 22  4  1  0
  4  3  1  6
  3  2  1  0
  2  1  2  3
  2  6  1  0
  6  7  1  1
  6  5  1  0
  6  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
 14 15  1  0
 11 20  1  1
 20 18  1  0
 18 19  2  0
 14 16  1  0
 18 16  1  0
 11 21  1  0
  5  4  1  0
 10  4  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 21 47  1  6
 22 48  1  1
 25 49  1  0
  3 28  1  0
  3 29  1  0
  1 26  1  0
  1 27  1  0
  7 32  1  0
  5 30  1  0
  5 31  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  1
 15 43  1  0
M  END


  Mrv1652309052201372D          

 25 29  0  0  1  0            999 V2000
    6.1457   -0.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4341   -1.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331   -0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -1.3568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6689   -1.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3493   -1.9378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1486   -2.1420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080   -2.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1559   -2.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6513   -2.1599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8111   -2.0778    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4387   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4841   -0.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7495   -0.2250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9062    0.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517   -0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4162    0.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6187   -1.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7941   -1.2175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0012   -1.9210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5867   -1.1491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3307   -0.8465    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4368   -0.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2009    0.7622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1983    0.2888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 11 20  1  6  0  0  0
 21 16  1  1  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204032

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12[C@H]3[C@H](C(O)=O)[C@@]45CC(=C)[C@@](O)(C4)CC[C@H]5[C@@]3(CC[C@@H]1O)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O6/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/h10-13,20,24H,1,3-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16?,17+,18+,19-/m1/s1

> <INCHI_KEY>
JLJLRLWOEMWYQK-QTWFBFKQSA-N

> <FORMULA>
C19H24O6

> <MOLECULAR_WEIGHT>
348.395

> <EXACT_MASS>
348.157288493

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.4552660488078

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,8S,9S,10R,12S)-5,12-dihydroxy-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_LOGP>
0.4010200203333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.44558757604102

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.195125021667938

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9049278919443272

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
85.60689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8S,9S,10R,12S)-5,12-dihydroxy-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

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      11.472  -1.220   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.144  -1.999   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.649  -1.346   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.486  -2.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.715  -3.149   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.985  -3.617   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.477  -3.998   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.348  -5.112   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.758  -5.355   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.816  -4.032   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.247  -3.879   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.419  -2.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.504  -0.926   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.132  -0.420   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.425   1.092   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.643  -0.813   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.644   0.359   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.022  -2.221   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.482  -2.273   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.735  -3.586   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.829  -2.145   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.217  -1.580   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.415  -0.053   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.975   1.423   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.837   0.539   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10   22                                             
CONECT    5    4    6                                                       
CONECT    6    5    2    7    8                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   20   21                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   21                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11                                                       
CONECT   21   16   11   22                                                  
CONECT   22   21    4   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄O₆

Average Mass

348.3950 Da

Monoisotopic Mass

348.15729 Da

IUPAC Name

(1R,2R,5S,8S,9S,10R,12S)-5,12-dihydroxy-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,5S,8S,9S,10R,12S)-5,12-dihydroxy-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@@]45CC(=C)[C@@](O)(C4)CC[C@H]5[C@@]3(CC[C@@H]1O)OC2=O

InChI Identifier

InChI=1S/C19H24O6/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/h10-13,20,24H,1,3-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16?,17+,18+,19-/m1/s1

InChI Key

JLJLRLWOEMWYQK-QTWFBFKQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Arabidopsis thaliana	LOTUS Database	35616633
Prunus armeniaca	LOTUS Database	35616633

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

Substituents

20-norgibberellane-6-carboxylic acid
Diterpene lactone
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.4	ChemAxon
pKa (Strongest Acidic)	4.2	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	85.61 m³·mol⁻¹	ChemAxon
Polarizability	35.46 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

388458

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439329

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hua Y, Ekkhara W, Sansenya S, Srisomsap C, Roytrakul S, Saburi W, Takeda R, Matsuura H, Mori H, Ketudat Cairns JR: Identification of rice Os4BGlu13 as a beta-glucosidase which hydrolyzes gibberellin A4 1-O-beta-d-glucosyl ester, in addition to tuberonic acid glucoside and salicylic acid derivative glucosides. Arch Biochem Biophys. 2015 Oct 1;583:36-46. doi: 10.1016/j.abb.2015.07.021. Epub 2015 Aug 1. [PubMed:26241499 ]
Arabia A, Munne-Bosch S, Munoz P: Melatonin triggers tissue-specific changes in anthocyanin and hormonal contents during postharvest decay of Angeleno plums. Plant Sci. 2022 Jul;320:111287. doi: 10.1016/j.plantsci.2022.111287. Epub 2022 Apr 15. [PubMed:35643621 ]
Pimenta Lange MJ, Szperlinski M, Kalix L, Lange T: Cucumber gibberellin 1-oxidase/desaturase initiates novel gibberellin catabolic pathways. J Biol Chem. 2020 Jun 19;295(25):8442-8448. doi: 10.1074/jbc.RA120.013708. Epub 2020 Apr 27. [PubMed:32345611 ]
Yang F, Fan Y, Wu X, Cheng Y, Liu Q, Feng L, Chen J, Wang Z, Wang X, Yong T, Liu W, Liu J, Du J, Shu K, Yang W: Auxin-to-Gibberellin Ratio as a Signal for Light Intensity and Quality in Regulating Soybean Growth and Matter Partitioning. Front Plant Sci. 2018 Jan 30;9:56. doi: 10.3389/fpls.2018.00056. eCollection 2018. [PubMed:29441084 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid (NP0204032)

MOL for NP0204032 ((1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid)

3D MOL for NP0204032 ((1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid)

3D SDF for NP0204032 ((1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid)

3D-SDF for NP0204032 ((1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid)

PDB for NP0204032 ((1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid)

3D PDB for NP0204032 ((1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid)

SMILES for NP0204032 ((1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid)

INCHI for NP0204032 ((1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid)

Structure for NP0204032 ((1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid)

3D Structure for NP0204032 ((1r,2r,5s,8s,9s,10r,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid)