NP-MRD: Showing NP-Card for Gibberellin A121 (NP0048994)

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Record Information

Version

2.0

Created at

2022-03-17 21:05:27 UTC

Updated at

2022-03-17 21:05:27 UTC

NP-MRD ID

NP0048994

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A121

Description

Gibberellin A121, also known as GA121, 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 A121 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, gibberellin A121 has been detected, but not quantified in, fruits and peachs. This could make gibberellin A121 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241207582D          

 24 28  0  0  0  0            999 V2000
   -1.0128   -0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459   -0.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3209   -0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640    0.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652    0.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    1.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1222    1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3725    0.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156   -0.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1281   -0.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6768    0.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4183    1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083    1.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7334   -0.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8899   -0.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6132   -0.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459   -1.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0609   -1.7839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691   -1.7839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652    1.5463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156    0.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6132    0.7942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2281   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9674    1.7839    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  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 21  1  0  0  0  0
  9 23  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
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048994

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC=CC3(OC1=O)C1CC(O)C4CC1(CC4=C)C(C23)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O5/c1-9-7-18-8-10(9)11(20)6-12(18)19-5-3-4-17(2,16(23)24-19)14(19)13(18)15(21)22/h3,5,10-14,20H,1,4,6-8H2,2H3,(H,21,22)

> <INCHI_KEY>
RAXXBLUAHMNNDW-UHFFFAOYSA-N

> <FORMULA>
C19H22O5

> <MOLECULAR_WEIGHT>
330.375

> <EXACT_MASS>
330.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.11087477988851

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-13-ene-9-carboxylic acid

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.2763518586666671

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.871153599446732

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.255565008862353

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8551952687695783

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
85.11839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-13-ene-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      -1.891  -0.117   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.646  -1.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.599  -0.117   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.119   1.349   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.428   1.346   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.465   2.478   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.961   2.147   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.429   0.679   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.389  -0.455   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.106  -0.430   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.130   0.718   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.647   2.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.135   2.494   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.369  -1.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.528  -0.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.878  -1.513   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.646  -2.560   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.980  -3.330   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.689  -3.330   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.428   2.886   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.389   1.085   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.878   1.483   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.159  -1.790   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.672   3.330   0.000  0.00  0.00           O+0
CONECT    1    2    5    9                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4   10   14                                             
CONECT    4    3    5   13                                                  
CONECT    5    1    4    6   20                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8   21   23                                             
CONECT   10    3   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   24                                                  
CONECT   13    4   12                                                       
CONECT   14    3   15                                                       
CONECT   15   11   14   16                                                  
CONECT   16   15                                                            
CONECT   17    2   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    5   21                                                       
CONECT   21    9   20   22                                                  
CONECT   22   21                                                            
CONECT   23    9                                                            
CONECT   24   12                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Value	Source
GA121	HMDB
4-Hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-13-ene-9-carboxylate	Generator

Chemical Formula

C₁₉H₂₂O₅

Average Mass

330.3750 Da

Monoisotopic Mass

330.14672 Da

IUPAC Name

4-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-13-ene-9-carboxylic acid

Traditional Name

4-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-13-ene-9-carboxylic acid

CAS Registry Number

357401-43-5

SMILES

CC12CC=CC3(OC1=O)C1CC(O)C4CC1(CC4=C)C(C23)C(O)=O

InChI Identifier

InChI=1S/C19H22O5/c1-9-7-18-8-10(9)11(20)6-12(18)19-5-3-4-17(2,16(23)24-19)14(19)13(18)15(21)22/h3,5,10-14,20H,1,4,6-8H2,2H3,(H,21,22)

InChI Key

RAXXBLUAHMNNDW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Prunus persica	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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
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	1.39	ALOGPS
logP	1.28	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-2.9	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	85.12 m³·mol⁻¹	ChemAxon
Polarizability	34.11 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

HMDB0038015

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017223

KNApSAcK ID

C00007867

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

131752274

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gibberellin A121 (NP0048994)

MOL for NP0048994 (Gibberellin A121)

3D MOL for NP0048994 (Gibberellin A121)

3D SDF for NP0048994 (Gibberellin A121)

3D-SDF for NP0048994 (Gibberellin A121)

PDB for NP0048994 (Gibberellin A121)

3D PDB for NP0048994 (Gibberellin A121)

SMILES for NP0048994 (Gibberellin A121)

INCHI for NP0048994 (Gibberellin A121)

Structure for NP0048994 (Gibberellin A121)

3D Structure for NP0048994 (Gibberellin A121)