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Showing NP-Card for Gibberellin A23 (NP0048632)

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Record Information
Version2.0
Created at2022-03-17 20:59:39 UTC
Updated at2022-03-17 20:59:39 UTC
NP-MRD IDNP0048632
Secondary Accession NumbersNone
Natural Product Identification
Common NameGibberellin A23
DescriptionGibberellin A23 belongs to the class of organic compounds known as c20-gibberellin 6-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position. Gibberellin A23 is found in Citrus reticulata, Cytisus laburnum, Leucaena leucocephala , Lupinus luteus and Wisteria floribunda . Gibberellin A23 is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048632 (Gibberellin A23)


  Mrv0541 02241216362D          

 27 30  0  0  0  0            999 V2000
   -0.6204    0.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8334   -0.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422   -0.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4968   -0.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2000    0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059    1.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    0.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189    0.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -0.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105   -0.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8258    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5276    1.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139    1.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9092   -0.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2382   -0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230    0.5518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -0.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422   -1.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8568   -1.9317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724   -1.9317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2211   -1.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0456   -1.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -1.8973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8702   -1.1826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074    1.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9914    1.9317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0159   -0.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 27  1  0  0  0  0
  9 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  2  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 26  2  0  0  0  0
M  END
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3D MOL for NP0048632 (Gibberellin A23)

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3D SDF for NP0048632 (Gibberellin A23)

  Mrv0541 02241216362D          

 27 30  0  0  0  0            999 V2000
   -0.6204    0.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8334   -0.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422   -0.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4968   -0.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2000    0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059    1.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    0.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189    0.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -0.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105   -0.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8258    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5276    1.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139    1.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9092   -0.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2382   -0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230    0.5518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -0.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422   -1.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8568   -1.9317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724   -1.9317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2211   -1.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0456   -1.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -1.8973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8702   -1.1826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074    1.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9914    1.9317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0159   -0.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 27  1  0  0  0  0
  9 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  2  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C2C(C(O)=O)C34CC(=C)C(O)(C3)CCC4C2(CCC1O)C=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O7/c1-10-7-19-8-20(10,27)6-3-11(19)18(9-21)5-4-12(22)17(2,16(25)26)14(18)13(19)15(23)24/h9,11-14,22,27H,1,3-8H2,2H3,(H,23,24)(H,25,26)

> <INCHI_KEY>
HRIAGYDCQBIJJM-UHFFFAOYSA-N

> <FORMULA>
C20H26O7

> <MOLECULAR_WEIGHT>
378.4162

> <EXACT_MASS>
378.167853186

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
38.01595534292612

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-formyl-5,12-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic acid

> <ALOGPS_LOGP>
0.28

> <JCHEM_LOGP>
0.22897212733333316

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.50472532453985

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8363127112387656

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9048934274056993

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
92.83789999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-formyl-5,12-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0048632 (Gibberellin A23)
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PDB for NP0048632 (Gibberellin A23)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.158   1.030   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.556  -0.458   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.265  -1.297   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.927  -0.329   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.373   1.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.251   2.118   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.742   1.715   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.142   0.222   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.049  -0.873   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.446  -0.566   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.408   0.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.852   2.059   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.333   2.292   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.697  -1.664   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.178  -0.704   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.896   1.030   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.630  -1.217   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.265  -2.836   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.599  -3.606   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.068  -3.606   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.279  -2.208   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.818  -2.208   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.049  -3.542   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.358  -2.208   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.760   2.518   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.851   3.606   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.630  -0.176   0.000  0.00  0.00           O+0
CONECT    1    2    5    6   25                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   10   14                                             
CONECT    5    1    4   13                                                  
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    2    8   21   22                                             
CONECT   10    4   11                                                       
CONECT   11   10   12   15   16                                             
CONECT   12   11   13                                                       
CONECT   13    5   12                                                       
CONECT   14    4   15                                                       
CONECT   15   11   14   17                                                  
CONECT   16   11                                                            
CONECT   17   15                                                            
CONECT   18    3   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    9                                                            
CONECT   22    9   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    1   26                                                       
CONECT   26   25                                                            
CONECT   27    8                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

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3D PDB for NP0048632 (Gibberellin A23)
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SMILES for NP0048632 (Gibberellin A23)
CC1(C2C(C(O)=O)C34CC(=C)C(O)(C3)CCC4C2(CCC1O)C=O)C(O)=O
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INCHI for NP0048632 (Gibberellin A23)
InChI=1S/C20H26O7/c1-10-7-19-8-20(10,27)6-3-11(19)18(9-21)5-4-12(22)17(2,16(25)26)14(18)13(19)15(23)24/h9,11-14,22,27H,1,3-8H2,2H3,(H,23,24)(H,25,26)
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SynonymsNot Available
Chemical FormulaC20H26O7
Average Mass378.4162 Da
Monoisotopic Mass378.16785 Da
IUPAC Name8-formyl-5,12-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic acid
Traditional Name8-formyl-5,12-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic acid
CAS Registry Number20134-29-6
SMILES
CC1(C2C(C(O)=O)C34CC(=C)C(O)(C3)CCC4C2(CCC1O)C=O)C(O)=O
InChI Identifier
InChI=1S/C20H26O7/c1-10-7-19-8-20(10,27)6-3-11(19)18(9-21)5-4-12(22)17(2,16(25)26)14(18)13(19)15(23)24/h9,11-14,22,27H,1,3-8H2,2H3,(H,23,24)(H,25,26)
InChI KeyHRIAGYDCQBIJJM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus reticulataLOTUS Database
Ipomoea batatasFooDB
Laburnum anagyroidesPlant
Leucaena glaucaPlant
Lupinus luteusPlant
Wisteria floribundaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as c20-gibberellin 6-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentC20-gibberellin 6-carboxylic acids  
Alternative Parents
Substituents
  • Gibberellane-6-carboxylic acid
    • 

  • Beta-hydroxy acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Hydroxy acid
    • 

  • Cyclic alcohol
    • 

  • Tertiary alcohol
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Aldehyde
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP0.28ALOGPS
logP0.23ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-0.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity92.84 m³·mol⁻¹ChemAxon
Polarizability38.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015857  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12310189  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available