NP-MRD: Showing NP-Card for Gibberellin A79 (NP0049461)

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Record Information

Version

2.0

Created at

2022-03-17 21:12:54 UTC

Updated at

2022-03-17 21:12:54 UTC

NP-MRD ID

NP0049461

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A79

Description

Gibberellin A79, also known as GA79, 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 A79 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, gibberellin A79 has been detected, but not quantified in, a few different foods, such as cereals and cereal products, common wheats, and wheats. Gibberellin A79 is found in Gibberella fujikuroi. This could make gibberellin A79 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218012D          

 26 30  0  0  0  0            999 V2000
   -1.4870   -0.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096   -0.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3796   -0.8857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707   -0.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7718    0.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7400   -1.5502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389    1.5502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163    1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0949    0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3796    0.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1263   -0.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541   -0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6452   -0.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3096    0.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2147    1.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5818    0.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    0.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400    1.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9932    2.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315    2.2779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5060   -1.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949   -1.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9174   -1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9174   -2.4360    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 25  1  0  0  0  0
  3  4  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  2  0  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 22  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv0541 02241218012D          

 26 30  0  0  0  0            999 V2000
   -1.4870   -0.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096   -0.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3796   -0.8857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707   -0.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7718    0.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7400   -1.5502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389    1.5502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163    1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0949    0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3796    0.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1263   -0.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541   -0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6452   -0.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3096    0.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2147    1.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5818    0.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    0.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400    1.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9932    2.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315    2.2779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5060   -1.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949   -1.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9174   -1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9174   -2.4360    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 25  1  0  0  0  0
  3  4  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  2  0  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 22  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049461

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12C3C(C(O)=O)C45CC(CCC4C3(OC1=O)C(O)C(O)C2O)C(=C)C5

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O7/c1-7-5-18-6-8(7)3-4-9(18)19-12(10(18)15(23)24)17(2,16(25)26-19)13(21)11(20)14(19)22/h8-14,20-22H,1,3-6H2,2H3,(H,23,24)

> <INCHI_KEY>
PVXFGQIIGNNJHW-UHFFFAOYSA-N

> <FORMULA>
C19H24O7

> <MOLECULAR_WEIGHT>
364.3897

> <EXACT_MASS>
364.152203122

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
36.159363719640254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12,13,14-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-0.2776725086666665

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.636228820629938

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.110555855890266

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4899303579157346

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
86.49379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12,13,14-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      -2.776  -1.417   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.311  -1.299   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -0.709  -1.653   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.244  -1.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.185  -0.059   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.307   0.886   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.248  -2.894   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.126   2.894   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.590   2.894   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.177   1.535   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.709   0.413   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.236  -0.767   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.594  -0.118   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.071  -0.590   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.311   0.354   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.134   1.890   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.953   1.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.712   1.418   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.712   2.894   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.248   3.189   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.721   4.547   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.059   4.252   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.945  -3.425   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.177  -2.421   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.712  -2.894   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.712  -4.547   0.000  0.00  0.00           O+0
CONECT    1    2    5   25                                                  
CONECT    2    1                                                            
CONECT    3    4   12                                                       
CONECT    4    3    5    7                                                  
CONECT    5    1    4    6   11                                             
CONECT    6    5                                                            
CONECT    7    4                                                            
CONECT    8    9                                                            
CONECT    9    8   10   22                                                  
CONECT   10    9   11   18                                                  
CONECT   11    5   10   12                                                  
CONECT   12    3   11   13   24                                             
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   10   13   17   19                                             
CONECT   19   18   20                                                       
CONECT   20   16   19   21                                                  
CONECT   21   20                                                            
CONECT   22    9                                                            
CONECT   23   24                                                            
CONECT   24   12   23   25                                                  
CONECT   25    1   24   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
GA79	HMDB
12,13,14-Trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylate	Generator

Chemical Formula

C₁₉H₂₄O₇

Average Mass

364.3897 Da

Monoisotopic Mass

364.15220 Da

IUPAC Name

12,13,14-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

Traditional Name

12,13,14-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

CAS Registry Number

132043-65-3

SMILES

CC12C3C(C(O)=O)C45CC(CCC4C3(OC1=O)C(O)C(O)C2O)C(=C)C5

InChI Identifier

InChI=1S/C19H24O7/c1-7-5-18-6-8(7)3-4-9(18)19-12(10(18)15(23)24)17(2,16(25)26-19)13(21)11(20)14(19)22/h8-14,20-22H,1,3-6H2,2H3,(H,23,24)

InChI Key

PVXFGQIIGNNJHW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fusarium fujikuroi	Fungi	KNApSAcK
Triticum aestivum	FooDB	KNAPSACK

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C19-gibberellin 6-carboxylic acids

Alternative Parents

Substituents

20-norgibberellane-6-carboxylic acid
2-hydroxy,20-norgibberellane
Diterpene lactone
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-0.28	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.49 m³·mol⁻¹	ChemAxon
Polarizability	36.16 Å³	ChemAxon
Number of Rings	5	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

HMDB0039623

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019251

KNApSAcK ID

C00000079

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

85366860

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gibberellin A79 (NP0049461)

MOL for NP0049461 (Gibberellin A79)

3D MOL for NP0049461 (Gibberellin A79)

3D SDF for NP0049461 (Gibberellin A79)

3D-SDF for NP0049461 (Gibberellin A79)

PDB for NP0049461 (Gibberellin A79)

3D PDB for NP0049461 (Gibberellin A79)

SMILES for NP0049461 (Gibberellin A79)

INCHI for NP0049461 (Gibberellin A79)

Structure for NP0049461 (Gibberellin A79)

3D Structure for NP0049461 (Gibberellin A79)