NP-MRD: Showing NP-Card for Gibberellin A43 (NP0048129)

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Record Information

Version

2.0

Created at

2022-03-17 20:51:33 UTC

Updated at

2022-03-17 20:51:33 UTC

NP-MRD ID

NP0048129

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A43

Description

Gibberellin A43, also known as GA43, belongs to the class of organic compounds known as c20-gibberellin 20-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position. Gibberellin A43 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, gibberellin A43 has been detected, but not quantified in, several different foods, such as common pea, fruits, japanese pumpkins, white lupines, and winter squash. Gibberellin A43 is found in Marah macrocarpa and Marah macrocarpus. This could make gibberellin A43 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308132D          

 28 31  0  0  0  0            999 V2000
   -0.6002    1.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2656    2.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385   -0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922    0.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879    2.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988    1.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6255    0.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1893    1.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4744    0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3686    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359    0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    2.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    1.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296    1.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    2.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232    2.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7476    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6465    1.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9435    1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0505    0.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1727    2.1169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852    3.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6844    3.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1229    2.6107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0992    3.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532   -0.2808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -0.3002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  8  1  2  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19  5  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20  7  1  0  0  0  0
 20 11  1  0  0  0  0
 20 13  1  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  2  0  0  0  0
 24 15  1  0  0  0  0
 25 16  2  0  0  0  0
 26 16  1  0  0  0  0
 27 17  2  0  0  0  0
 28 17  1  0  0  0  0
M  END


  Mrv0541 05061308132D          

 28 31  0  0  0  0            999 V2000
   -0.6002    1.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2656    2.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385   -0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922    0.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879    2.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988    1.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6255    0.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1893    1.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4744    0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3686    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359    0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    2.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    1.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296    1.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    2.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232    2.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7476    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6465    1.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9435    1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0505    0.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1727    2.1169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852    3.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6844    3.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1229    2.6107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0992    3.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532   -0.2808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -0.3002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  8  1  2  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19  5  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20  7  1  0  0  0  0
 20 11  1  0  0  0  0
 20 13  1  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  2  0  0  0  0
 24 15  1  0  0  0  0
 25 16  2  0  0  0  0
 26 16  1  0  0  0  0
 27 17  2  0  0  0  0
 28 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C2C(C(O)=O)C34CC(CCC3C2(CC(O)C1O)C(O)=O)C(=C)C4)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O8/c1-8-5-19-6-9(8)3-4-11(19)20(17(27)28)7-10(21)14(22)18(2,16(25)26)13(20)12(19)15(23)24/h9-14,21-22H,1,3-7H2,2H3,(H,23,24)(H,25,26)(H,27,28)

> <INCHI_KEY>
FQTLNSKVFLETSS-UHFFFAOYSA-N

> <FORMULA>
C20H26O8

> <MOLECULAR_WEIGHT>
394.4156

> <EXACT_MASS>
394.162767808

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
38.74222763682103

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
0.47198453766666676

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.118231104675916

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.57992026928405

> <JCHEM_PKA_STRONGEST_BASIC>
-3.17905798159196

> <JCHEM_POLAR_SURFACE_AREA>
152.36

> <JCHEM_REFRACTIVITY>
93.59669999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.120   3.304   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.096   5.399   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.752  -0.018   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.345   0.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.657   3.839   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.051   2.096   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.768   1.077   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.353   2.857   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.886   1.337   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.155   1.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.987   1.554   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.174   4.077   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.609   3.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.269   3.282   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.861   5.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.070   5.252   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.231   0.427   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.996   4.149   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.073   2.937   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.495   1.944   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.428   0.880   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.656   3.952   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.399   6.068   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.011   6.610   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.563   4.873   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.652   6.734   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.019  -0.524   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.413  -0.560   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   18                                                            
CONECT    3    4    9                                                       
CONECT    4    3   11                                                       
CONECT    5    8   19                                                       
CONECT    6    9   19                                                       
CONECT    7   10   20                                                       
CONECT    8    1    5    9                                                  
CONECT    9    3    6    8                                                  
CONECT   10    7   14   21                                                  
CONECT   11    4   19   20                                                  
CONECT   12   13   15   19                                                  
CONECT   13   12   18   20                                                  
CONECT   14   10   18   22                                                  
CONECT   15   12   23   24                                                  
CONECT   16   18   25   26                                                  
CONECT   17   20   27   28                                                  
CONECT   18    2   13   14   16                                             
CONECT   19    5    6   11   12                                             
CONECT   20    7   11   13   17                                             
CONECT   21   10                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   17                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
GA43	HMDB
5,6-Dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate	Generator

Chemical Formula

C₂₀H₂₆O₈

Average Mass

394.4156 Da

Monoisotopic Mass

394.16277 Da

IUPAC Name

5,6-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid

Traditional Name

5,6-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid

CAS Registry Number

54605-43-5

SMILES

CC1(C2C(C(O)=O)C34CC(CCC3C2(CC(O)C1O)C(O)=O)C(=C)C4)C(O)=O

InChI Identifier

InChI=1S/C20H26O8/c1-8-5-19-6-9(8)3-4-11(19)20(17(27)28)7-10(21)14(22)18(2,16(25)26)13(20)12(19)15(23)24/h9-14,21-22H,1,3-7H2,2H3,(H,23,24)(H,25,26)(H,27,28)

InChI Key

FQTLNSKVFLETSS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cucurbita maxima	FooDB	KNAPSACK
Lupinus albus	FooDB	KNAPSACK
Marah macrocarpa	LOTUS Database	35616633
Marah macrocarpus	Plant	KNApSAcK
Pisum sativum	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c20-gibberellin 20-carboxylic acids. These are c20-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

C20-gibberellin 20-carboxylic acids

Alternative Parents

Substituents

Gibberellane-6-carboxylic acid
Gibberellane-20-carboxylic acid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Secondary alcohol
1,2-diol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Carbonyl group
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	0.17	ALOGPS
logP	0.47	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	152.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.6 m³·mol⁻¹	ChemAxon
Polarizability	38.74 Å³	ChemAxon
Number of Rings	4	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

HMDB0035046

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013663

KNApSAcK ID

C00000043

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14833730

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gibberellin A43 (NP0048129)

MOL for NP0048129 (Gibberellin A43)

3D MOL for NP0048129 (Gibberellin A43)

3D SDF for NP0048129 (Gibberellin A43)

3D-SDF for NP0048129 (Gibberellin A43)

PDB for NP0048129 (Gibberellin A43)

3D PDB for NP0048129 (Gibberellin A43)

SMILES for NP0048129 (Gibberellin A43)

INCHI for NP0048129 (Gibberellin A43)

Structure for NP0048129 (Gibberellin A43)

3D Structure for NP0048129 (Gibberellin A43)