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Showing NP-Card for 16, 17-dihydro-16α, 17-dihydroxy GA9 (NP0334303)

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Record Information
Version2.0
Created at2024-09-09 23:04:23 UTC
Updated at2024-09-09 23:04:23 UTC
NP-MRD IDNP0334303
Secondary Accession NumbersNone
Natural Product Identification
Common Name16, 17-dihydro-16α, 17-dihydroxy GA9
Description16, 17-Dihydro-16Œ±, 17-dihydroxy ga9 is also known as 16α, 17-[oh]2 gibberellin a9. 16, 17-Dihydro-16Œ±, 17-dihydroxy ga9 is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 16, 17-Dihydro-16Œ±, 17-dihydroxy ga9 can be found in a number of food items such as spirulina, leek, tinda, and fenugreek, which makes 16, 17-dihydro-16Œ±, 17-dihydroxy ga9 a potential biomarker for the consumption of these food products.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334303 (16, 17-dihydro-16α, 17-dihydroxy GA9)


  Mrv2104 05252301362D          

 29 33  0  0  1  0            999 V2000
   -1.4079    3.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7798    2.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9976    1.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1451    0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0910    3.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5491    2.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6961    2.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    3.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3319    2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667    1.7864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7038    1.6926    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4345    3.0210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2877    2.6070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4991    3.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567    2.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959    3.3438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0961    2.4891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5471    2.6300    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0978    1.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9447    2.9279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1809    4.3106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2437    4.1988    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.0816    2.6049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809    3.3845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    1.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    1.5216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3043    0.9708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3843    3.1212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370    2.6281    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  1  1  1  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 16  5  1  0  0  0  0
  6 19  1  0  0  0  0
 10  7  1  0  0  0  0
 17  7  1  6  0  0  0
 17  8  1  0  0  0  0
 18  8  1  0  0  0  0
 18  9  1  1  0  0  0
  9 20  1  0  0  0  0
 10 26  1  1  0  0  0
 10 18  1  0  0  0  0
 11 27  1  6  0  0  0
 17 11  1  0  0  0  0
 11 19  1  0  0  0  0
 12 28  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  6  0  0  0
 12 17  1  0  0  0  0
 13 29  1  6  0  0  0
 13 16  1  0  0  0  0
 13 19  1  0  0  0  0
 14 21  2  0  0  0  0
 14 22  1  0  0  0  0
 16 15  1  0  0  0  0
 15 23  2  0  0  0  0
 15 25  1  0  0  0  0
 18 24  1  6  0  0  0
 19 25  1  0  0  0  0
M  CHG  1  22  -1
M  END
Download

3D MOL for NP0334303 (16, 17-dihydro-16α, 17-dihydroxy GA9)

Download
3D SDF for NP0334303 (16, 17-dihydro-16α, 17-dihydroxy GA9)

  Mrv2104 05252301362D          

 29 33  0  0  1  0            999 V2000
   -1.4079    3.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7798    2.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9976    1.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1451    0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0910    3.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5491    2.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6961    2.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    3.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3319    2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667    1.7864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7038    1.6926    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4345    3.0210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2877    2.6070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4991    3.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567    2.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959    3.3438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0961    2.4891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5471    2.6300    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0978    1.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9447    2.9279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1809    4.3106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2437    4.1988    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.0816    2.6049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809    3.3845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    1.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    1.5216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3043    0.9708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3843    3.1212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370    2.6281    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  1  1  1  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 16  5  1  0  0  0  0
  6 19  1  0  0  0  0
 10  7  1  0  0  0  0
 17  7  1  6  0  0  0
 17  8  1  0  0  0  0
 18  8  1  0  0  0  0
 18  9  1  1  0  0  0
  9 20  1  0  0  0  0
 10 26  1  1  0  0  0
 10 18  1  0  0  0  0
 11 27  1  6  0  0  0
 17 11  1  0  0  0  0
 11 19  1  0  0  0  0
 12 28  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  6  0  0  0
 12 17  1  0  0  0  0
 13 29  1  6  0  0  0
 13 16  1  0  0  0  0
 13 19  1  0  0  0  0
 14 21  2  0  0  0  0
 14 22  1  0  0  0  0
 16 15  1  0  0  0  0
 15 23  2  0  0  0  0
 15 25  1  0  0  0  0
 18 24  1  6  0  0  0
 19 25  1  0  0  0  0
M  CHG  1  22  -1
M  END
> <DATABASE_ID>
NP0334303

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@]3(C[C@@]1(O)CO)[C@@]([H])(CC2)C12CCC[C@@](C)(C(=O)O1)[C@@]2([H])[C@]3([H])C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O6/c1-16-5-2-6-19(25-15(16)23)11-4-3-10-7-17(11,8-18(10,24)9-20)12(13(16)19)14(21)22/h10-13,20,24H,2-9H2,1H3,(H,21,22)/p-1/t10-,11-,12-,13-,16-,17+,18-,19?/m1/s1

> <INCHI_KEY>
OXEMPUBMLFVGQQ-HFDQALKSSA-M

> <FORMULA>
C19H25O6

> <MOLECULAR_WEIGHT>
349.404

> <EXACT_MASS>
349.165662105

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
67.48329739292545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.7766594716666662

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.685464827921201

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.226820524436847

> <JCHEM_PKA_STRONGEST_BASIC>
-3.075766535749131

> <JCHEM_POLAR_SURFACE_AREA>
106.89000000000001

> <JCHEM_REFRACTIVITY>
96.84869999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334303 (16, 17-dihydro-16α, 17-dihydroxy GA9)
Download
PDB for NP0334303 (16, 17-dihydro-16α, 17-dihydroxy GA9)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      -2.628   7.449   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.456   5.519   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.729   1.881   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.137   1.762   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.170   6.579   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.025   4.074   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.166   3.941   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.338   5.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.220   4.434   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.418   3.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.314   3.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.811   5.639   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.537   4.866   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.932   7.174   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.346   4.857   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.672   6.242   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.046   4.646   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.755   4.909   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.183   3.119   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.363   5.465   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.338   8.046   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.321   7.838   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0      -3.886   4.862   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.378   6.318   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.683   3.467   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       5.876   2.840   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.568   1.812   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.717   5.826   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.002   4.906   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2    5    6                                                       
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    2   16                                                       
CONECT    6    2   19                                                       
CONECT    7   10   17                                                       
CONECT    8   17   18                                                       
CONECT    9   18   20                                                       
CONECT   10    3    7   26   18                                             
CONECT   11    4   27   17   19                                             
CONECT   12   28   13   14   17                                             
CONECT   13   12   29   16   19                                             
CONECT   14   12   21   22                                                  
CONECT   15   16   23   25                                                  
CONECT   16    1    5   13   15                                             
CONECT   17    7    8   11   12                                             
CONECT   18    8    9   10   24                                             
CONECT   19    6   11   13   25                                             
CONECT   20    9                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   18                                                            
CONECT   25   15   19                                                       
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

Download
3D PDB for NP0334303 (16, 17-dihydro-16α, 17-dihydroxy GA9)
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SMILES for NP0334303 (16, 17-dihydro-16α, 17-dihydroxy GA9)
[H][C@@]12C[C@]3(C[C@@]1(O)CO)[C@@]([H])(CC2)C12CCC[C@@](C)(C(=O)O1)[C@@]2([H])[C@]3([H])C([O-])=O
Download
INCHI for NP0334303 (16, 17-dihydro-16α, 17-dihydroxy GA9)
InChI=1S/C19H26O6/c1-16-5-2-6-19(25-15(16)23)11-4-3-10-7-17(11,8-18(10,24)9-20)12(13(16)19)14(21)22/h10-13,20,24H,2-9H2,1H3,(H,21,22)/p-1/t10-,11-,12-,13-,16-,17+,18-,19?/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC19H25O6
Average Mass349.4040 Da
Monoisotopic Mass349.16566 Da
IUPAC Name(2R,5R,6S,8S,9S,10R,11R)-6-hydroxy-6-(hydroxymethyl)-11-methyl-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylate
Traditional Name(2R,5R,6S,8S,9S,10R,11R)-6-hydroxy-6-(hydroxymethyl)-11-methyl-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylate
CAS Registry NumberNot Available
SMILES
[H][C@@]12C[C@]3(C[C@@]1(O)CO)[C@@]([H])(CC2)C12CCC[C@@](C)(C(=O)O1)[C@@]2([H])[C@]3([H])C([O-])=O
InChI Identifier
InChI=1S/C19H26O6/c1-16-5-2-6-19(25-15(16)23)11-4-3-10-7-17(11,8-18(10,24)9-20)12(13(16)19)14(21)22/h10-13,20,24H,2-9H2,1H3,(H,21,22)/p-1/t10-,11-,12-,13-,16-,17+,18-,19?/m1/s1
InChI KeyOXEMPUBMLFVGQQ-HFDQALKSSA-M
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentC19-gibberellin 6-carboxylic acids  
Alternative Parents
Substituents
  • 20-norgibberellane-6-carboxylic acid
    • 

  • Diterpene lactone
    • 

  • Caprolactone
    • 

  • Short-chain hydroxy acid
    • 

  • Oxepane
    • 

  • Hydroxy fatty acid
    • 

  • Heterocyclic fatty acid
    • 

  • Fatty acid ester
    • 

  • Branched fatty acid
    • 

  • Fatty acyl
    • 

  • Gamma butyrolactone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Organic anion
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.78ChemAxon
pKa (Strongest Acidic)4.23ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area106.89 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.85 m³·mol⁻¹ChemAxon
Polarizability67.48 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References