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Showing NP-Card for Gibberellin A21 (NP0050177)

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Record Information
Version2.0
Created at2022-04-27 20:29:48 UTC
Updated at2022-04-27 20:29:49 UTC
NP-MRD IDNP0050177
Secondary Accession NumbersNone
Natural Product Identification
Common NameGibberellin A21
Description18450-93-6 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. Gibberellin A21 is found in Canavalia gladiata . 18450-93-6 Is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050177 (Gibberellin A21)


  Mrv1652307222018542D          

 28 32  0  0  1  0            999 V2000
    0.1401   -0.5591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0860    0.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    1.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398    1.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1452    0.7794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8609    1.4823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4440    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9958    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203    0.1046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7879    0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144   -0.0036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958   -1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -1.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5356    1.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553   -1.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433    0.5212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6433   -0.3038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6433    1.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620    0.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620   -0.7260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8032   -0.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733    0.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733   -0.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -1.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1984    0.0230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433   -1.1253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770   -1.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480   -1.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9  2  1  6  0  0  0
  6  2  1  6  0  0  0
  8 10  2  0  0  0  0
  1  9  1  0  0  0  0
  5 11  1  1  0  0  0
  6 14  1  0  0  0  0
  1 12  1  1  0  0  0
 12 13  2  0  0  0  0
 12 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  6  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  2  0  0  0  0
 20 21  1  6  0  0  0
 22 23  1  0  0  0  0
 17 26  1  1  0  0  0
 16  5  1  0  0  0  0
 17  1  1  0  0  0  0
 24 28  2  0  0  0  0
 24 27  1  0  0  0  0
M  END
Download

3D MOL for NP0050177 (Gibberellin A21)

Download
3D SDF for NP0050177 (Gibberellin A21)

  Mrv1652307222018542D          

 28 32  0  0  1  0            999 V2000
    0.1401   -0.5591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0860    0.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    1.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398    1.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1452    0.7794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8609    1.4823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4440    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9958    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203    0.1046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7879    0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144   -0.0036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958   -1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -1.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5356    1.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553   -1.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433    0.5212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6433   -0.3038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6433    1.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620    0.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620   -0.7260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8032   -0.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733    0.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733   -0.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -1.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1984    0.0230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433   -1.1253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770   -1.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480   -1.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9  2  1  6  0  0  0
  6  2  1  6  0  0  0
  8 10  2  0  0  0  0
  1  9  1  0  0  0  0
  5 11  1  1  0  0  0
  6 14  1  0  0  0  0
  1 12  1  1  0  0  0
 12 13  2  0  0  0  0
 12 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  6  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  2  0  0  0  0
 20 21  1  6  0  0  0
 22 23  1  0  0  0  0
 17 26  1  1  0  0  0
 16  5  1  0  0  0  0
 17  1  1  0  0  0  0
 24 28  2  0  0  0  0
 24 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050177

> <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@@]22CCC[C@@]1(C(O)=O)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O7/c1-9-7-16-8-17(9,25)6-3-10(16)19-5-2-4-18(14(22)23,15(24)26-19)12(19)11(16)13(20)21/h10-12,25H,1-8H2,(H,20,21)(H,22,23)/t10-,11-,12-,16+,17+,18-,19-/m1/s1

> <INCHI_KEY>
HILUWRPVFKJTAD-ZGHMGGRHSA-N

> <FORMULA>
C19H22O7

> <MOLECULAR_WEIGHT>
362.378

> <EXACT_MASS>
362.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.540225057819754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
0.8235236863333337

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.319093172968279

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6323446278213156

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9049376952890639

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000002

> <JCHEM_REFRACTIVITY>
85.80859999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050177 (Gibberellin A21)
Download
PDB for NP0050177 (Gibberellin A21)
HEADER    PROTEIN                                 22-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUL-20         0                                  
HETATM    1  C   UNK     0       0.261  -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      -2.540  -2.465   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  H   UNK     0      -1.201  -2.101   0.000  0.00  0.00           H+0
HETATM   27  O   UNK     0      -3.877  -3.228   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.210  -3.241   0.000  0.00  0.00           O+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   26    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   22                                                       
CONECT   24   20   28   27                                                  
CONECT   25   21                                                            
CONECT   26   17                                                            
CONECT   27   24                                                            
CONECT   28   24                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

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3D PDB for NP0050177 (Gibberellin A21)
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SMILES for NP0050177 (Gibberellin A21)
[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@@]22CCC[C@@]1(C(O)=O)C(=O)O2
Download
INCHI for NP0050177 (Gibberellin A21)
InChI=1S/C19H22O7/c1-9-7-16-8-17(9,25)6-3-10(16)19-5-2-4-18(14(22)23,15(24)26-19)12(19)11(16)13(20)21/h10-12,25H,1-8H2,(H,20,21)(H,22,23)/t10-,11-,12-,16+,17+,18-,19-/m1/s1
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View in JSmol
Synonyms
ValueSource
Canavalia gibberellin IHMDB
GA21HMDB
Gibberellin A21HMDB
Chemical FormulaC19H22O7
Average Mass362.3780 Da
Monoisotopic Mass362.13655 Da
IUPAC Name(1R,2R,5S,8S,9S,10R,11R)-5-hydroxy-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9,11-dicarboxylic acid
Traditional Name(1R,2R,5S,8S,9S,10R,11R)-5-hydroxy-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9,11-dicarboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@@]22CCC[C@@]1(C(O)=O)C(=O)O2
InChI Identifier
InChI=1S/C19H22O7/c1-9-7-16-8-17(9,25)6-3-10(16)19-5-2-4-18(14(22)23,15(24)26-19)12(19)11(16)13(20)21/h10-12,25H,1-8H2,(H,20,21)(H,22,23)/t10-,11-,12-,16+,17+,18-,19-/m1/s1
InChI KeyHILUWRPVFKJTAD-ZGHMGGRHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Canavalia gladiataPlant
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
    • 

  • Tricarboxylic acid or derivatives
    • 

  • Caprolactone
    • 

  • Oxepane
    • 

  • Gamma butyrolactone
    • 

  • Cyclic alcohol
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • 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
logP0.62ALOGPS
logP0.82ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-0.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.81 m³·mol⁻¹ChemAxon
Polarizability35.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035050  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013670  
KNApSAcK IDC00000021  
Chemspider ID68024203  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101603106  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available