NP-MRD: Showing NP-Card for Gibberellin A74 (NP0049210)

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Record Information

Version

2.0

Created at

2022-03-17 21:08:51 UTC

Updated at

2022-03-17 21:08:51 UTC

NP-MRD ID

NP0049210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A74

Description

Gibberellin A74, also known as GA74, 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 A74 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, gibberellin A74 has been detected, but not quantified in, a few different foods, such as fruits, japanese pumpkins, and winter squash. This could make gibberellin A74 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310372D          

 26 29  0  0  0  0            999 V2000
    0.0376    0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    2.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9031   -0.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060    1.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630    1.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4298    2.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5256    0.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270    0.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    1.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762    2.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735    1.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0670    0.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736    0.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6421    0.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062   -0.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9607   -0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5810    1.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851    0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    0.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1986    3.1748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8101    0.3147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9229   -0.8191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220   -1.1091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7603   -0.1790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7367   -1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  9  1  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13  4  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  5  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  7  1  0  0  0  0
 20  8  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 22 13  1  0  0  0  0
 23 16  2  0  0  0  0
 24 16  1  0  0  0  0
 25 17  2  0  0  0  0
 26 17  1  0  0  0  0
M  END


  Mrv0541 05061310372D          

 26 29  0  0  0  0            999 V2000
    0.0376    0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    2.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9031   -0.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060    1.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630    1.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4298    2.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5256    0.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270    0.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    1.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762    2.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735    1.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0670    0.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736    0.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6421    0.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062   -0.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9607   -0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5810    1.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851    0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    0.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1986    3.1748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8101    0.3147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9229   -0.8191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220   -1.1091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7603   -0.1790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7367   -1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  9  1  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13  4  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  5  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  7  1  0  0  0  0
 20  8  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 22 13  1  0  0  0  0
 23 16  2  0  0  0  0
 24 16  1  0  0  0  0
 25 17  2  0  0  0  0
 26 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049210

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC(O)C(C)(C1C(C(O)=O)C13CC(C(O)CC21)C(=C)C3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-9-7-20-8-10(9)11(21)6-12(20)18(2)5-4-13(22)19(3,17(25)26)15(18)14(20)16(23)24/h10-15,21-22H,1,4-8H2,2-3H3,(H,23,24)(H,25,26)

> <INCHI_KEY>
RKDWVYHBXWADKI-UHFFFAOYSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.4327

> <EXACT_MASS>
364.188588628

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
37.790629833399976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,11-dihydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic acid

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
1.0464307486666669

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.668035986532983

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9958207543384123

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8946257333248263

> <JCHEM_POLAR_SURFACE_AREA>
115.06000000000002

> <JCHEM_REFRACTIVITY>
92.11049999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,11-dihydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic 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       0.070   1.235   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.421   4.112   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.286  -0.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.345   2.792   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.958   3.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.536   4.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.848   0.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.241   2.443   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.544   1.682   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.076   3.202   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.942   4.557   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.177   2.985   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.458   1.257   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.364   0.462   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.799   1.059   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.052  -1.046   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.260  -0.713   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.685   2.595   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.186   0.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.264   1.602   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.237   5.926   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.846   0.587   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.589  -1.529   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.201  -2.070   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.753  -0.334   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.842  -2.195   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4    5   13                                                       
CONECT    5    4   18                                                       
CONECT    6   11   12                                                       
CONECT    7    9   20                                                       
CONECT    8   10   20                                                       
CONECT    9    1    7   10                                                  
CONECT   10    8    9   11                                                  
CONECT   11    6   10   21                                                  
CONECT   12    6   18   20                                                  
CONECT   13    4   19   22                                                  
CONECT   14   15   16   20                                                  
CONECT   15   14   18   19                                                  
CONECT   16   14   23   24                                                  
CONECT   17   19   25   26                                                  
CONECT   18    2    5   12   15                                             
CONECT   19    3   13   15   17                                             
CONECT   20    7    8   12   14                                             
CONECT   21   11                                                            
CONECT   22   13                                                            
CONECT   23   16                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26   17                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
GA74	HMDB
5,11-Dihydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylate	Generator

Chemical Formula

C₂₀H₂₈O₆

Average Mass

364.4327 Da

Monoisotopic Mass

364.18859 Da

IUPAC Name

5,11-dihydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic acid

Traditional Name

5,11-dihydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic acid

CAS Registry Number

90806-14-7

SMILES

CC12CCC(O)C(C)(C1C(C(O)=O)C13CC(C(O)CC21)C(=C)C3)C(O)=O

InChI Identifier

InChI=1S/C20H28O6/c1-9-7-20-8-10(9)11(21)6-12(20)18(2)5-4-13(22)19(3,17(25)26)15(18)14(20)16(23)24/h10-15,21-22H,1,4-8H2,2-3H3,(H,23,24)(H,25,26)

InChI Key

RKDWVYHBXWADKI-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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C20-gibberellin 6-carboxylic acids

Alternative Parents

Substituents

Gibberellane-6-carboxylic acid
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.92	ALOGPS
logP	1.05	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-0.89	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.11 m³·mol⁻¹	ChemAxon
Polarizability	37.79 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

HMDB0038746

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018157

KNApSAcK ID

C00000074

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

131752448

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gibberellin A74 (NP0049210)

MOL for NP0049210 (Gibberellin A74)

3D MOL for NP0049210 (Gibberellin A74)

3D SDF for NP0049210 (Gibberellin A74)

3D-SDF for NP0049210 (Gibberellin A74)

PDB for NP0049210 (Gibberellin A74)

3D PDB for NP0049210 (Gibberellin A74)

SMILES for NP0049210 (Gibberellin A74)

INCHI for NP0049210 (Gibberellin A74)

Structure for NP0049210 (Gibberellin A74)

3D Structure for NP0049210 (Gibberellin A74)