NP-MRD: Showing NP-Card for Gibberellin A61 (NP0048098)

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Record Information

Version

2.0

Created at

2022-03-17 20:51:02 UTC

Updated at

2022-03-17 20:51:03 UTC

NP-MRD ID

NP0048098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A61

Description

Gibberellin A61, also known as GA61, 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 A61 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, gibberellin A61 has been detected, but not quantified in, several different foods, such as wheats, loquats, common wheats, peachs, and cereals and cereal products. Gibberellin A61 is found in Anemia mexicana, Malus domestica , Ornithogalum thyrsoides, Prunus persica L. and Pyrus malus . This could make gibberellin A61 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214332D          

 24 28  0  0  0  0            999 V2000
   -0.6261   -1.2260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1998   -1.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389   -1.6955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3563    1.2260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5738    1.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1565    0.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6261   -0.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0519   -0.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6261   -0.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4606   -0.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -0.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0348    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087    0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780    0.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780    1.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129    1.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8259    2.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607    2.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0867    0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0433   -1.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -1.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3650   -2.1651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  2  0  0  0  0
  2 20  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 18  1  0  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 20  1  0  0  0  0
  8  9  1  0  0  0  0
  8 23  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC(O)C3(OC1=O)C1CCC4CC1(CC4=C)C(C23)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O5/c1-9-7-18-8-10(9)3-4-11(18)19-12(20)5-6-17(2,16(23)24-19)14(19)13(18)15(21)22/h10-14,20H,1,3-8H2,2H3,(H,21,22)

> <INCHI_KEY>
JKQCGVABHHQYKQ-UHFFFAOYSA-N

> <FORMULA>
C19H24O5

> <MOLECULAR_WEIGHT>
332.3909

> <EXACT_MASS>
332.162373878

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.617292855851446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.7162272453333332

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.949661426814846

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.288333475925309

> <JCHEM_PKA_STRONGEST_BASIC>
-3.258898335637607

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
83.92479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-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  O   UNK     0      -1.169  -2.289   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.240  -2.191   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.993  -3.165   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.532   2.289   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.071   2.289   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.292   1.022   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.169  -0.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.097  -1.411   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.169  -0.730   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.726  -1.217   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.993  -0.243   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.798   1.315   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.630   0.633   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.266   0.828   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.266   2.289   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.824   2.581   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.408   4.042   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.487   3.749   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.895   0.146   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.630  -0.730   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.630  -2.775   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.947  -3.554   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.487  -3.067   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.681  -4.042   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2                                                            
CONECT    4    5                                                            
CONECT    5    4    6   18                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   20                                                  
CONECT    8    1    7    9   23                                             
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14    6    9   13   15                                             
CONECT   15   14   16                                                       
CONECT   16   12   15   17                                                  
CONECT   17   16                                                            
CONECT   18    5                                                            
CONECT   19   20                                                            
CONECT   20    2    7   19   21                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23    8   22   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Value	Source
GA61	HMDB
14-Hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylate	Generator

Chemical Formula

C₁₉H₂₄O₅

Average Mass

332.3909 Da

Monoisotopic Mass

332.16237 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

81826-98-4

SMILES

CC12CCC(O)C3(OC1=O)C1CCC4CC1(CC4=C)C(C23)C(O)=O

InChI Identifier

InChI=1S/C19H24O5/c1-9-7-18-8-10(9)3-4-11(18)19-12(20)5-6-17(2,16(23)24-19)14(19)13(18)15(21)22/h10-14,20H,1,3-8H2,2H3,(H,21,22)

InChI Key

JKQCGVABHHQYKQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anemia mexicana	Plant	KNApSAcK
Eriobotrya japonica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Malus domestica	Plant	KNApSAcK
Malus pumila	FooDB	KNAPSACK
Ornithogalum thyrsoides	Plant	KNApSAcK
Prunus persica	FooDB	KNAPSACK
Prunus persica L.	Plant	KNApSAcK
Pyrus malus	Plant	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
Diterpene lactone
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen 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	1.34	ALOGPS
logP	1.72	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.92 m³·mol⁻¹	ChemAxon
Polarizability	34.62 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

HMDB0034987

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013590

KNApSAcK ID

C00007876

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

14605551

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gibberellin A61 (NP0048098)

MOL for NP0048098 (Gibberellin A61)

3D MOL for NP0048098 (Gibberellin A61)

3D SDF for NP0048098 (Gibberellin A61)

3D-SDF for NP0048098 (Gibberellin A61)

PDB for NP0048098 (Gibberellin A61)

3D PDB for NP0048098 (Gibberellin A61)

SMILES for NP0048098 (Gibberellin A61)

INCHI for NP0048098 (Gibberellin A61)

Structure for NP0048098 (Gibberellin A61)

3D Structure for NP0048098 (Gibberellin A61)