NP-MRD: Showing NP-Card for Gibberellin A36 (NP0050183)

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Record Information

Version

2.0

Created at

2022-04-27 20:30:02 UTC

Updated at

2022-04-27 20:30:02 UTC

NP-MRD ID

NP0050183

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A36

Description

Gibberellin A36, also known as GA36, 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. Thus, gibberellin A36 is considered to be an isoprenoid. Gibberellin A36 is found in Arabidopsis thaliana, Cucurbita maxima , Dioscorea polystachya, Gibberella fujikuroi, Psilotum nudum, Saccharum spp. and Sphaceloma manihoticola. Based on a literature review very few articles have been published on gibberellin A36.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222302D          

 26 29  0  0  1  0            999 V2000
    3.3060    1.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601    0.5041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6741    0.0457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9342    0.4105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8801    1.2337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5660    1.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    1.4630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5753    0.7329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1577    0.1142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9732   -0.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5773   -1.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1846   -0.9322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175    1.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    1.5339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1721    2.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    2.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    0.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1471    0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509    2.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919    2.5679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3354   -0.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1084   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7179   -1.3826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -0.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1000    0.1393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  1  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  8 19  1  0  0  0  0
  5 20  1  1  0  0  0
 20 21  2  0  0  0  0
  3 22  1  6  0  0  0
  3 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  2 26  1  6  0  0  0
M  END


  Mrv1652304272222302D          

 26 29  0  0  1  0            999 V2000
    3.3060    1.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601    0.5041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6741    0.0457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9342    0.4105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8801    1.2337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5660    1.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    1.4630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5753    0.7329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1577    0.1142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9732   -0.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5773   -1.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1846   -0.9322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175    1.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    1.5339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1721    2.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    2.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    0.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1471    0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509    2.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919    2.5679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3354   -0.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1084   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7179   -1.3826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -0.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1000    0.1393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  1  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  8 19  1  0  0  0  0
  5 20  1  1  0  0  0
 20 21  2  0  0  0  0
  3 22  1  6  0  0  0
  3 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  2 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050183

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1([C@H]2[C@H](C(O)=O)[C@@]34C[C@@H](CC[C@H]3[C@@]2(CC[C@@H]1O)C=O)C(=C)C4)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O6/c1-10-7-20-8-11(10)3-4-12(20)19(9-21)6-5-13(22)18(2,17(25)26)15(19)14(20)16(23)24/h9,11-15,22H,1,3-8H2,2H3,(H,23,24)(H,25,26)/t11-,12+,13+,14-,15-,18-,19-,20+/m1/s1

> <INCHI_KEY>
JZBLVVPDEDCVQA-SQLMURCQSA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.422

> <EXACT_MASS>
362.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.00654040560889

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3S,4S,5S,8R,9R,12R)-8-formyl-5-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4-dicarboxylic acid

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
1.3882718923333344

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.592553504633369

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.920608162359104

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0387693195355956

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
91.30979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4S,5S,8R,9R,12R)-8-formyl-5-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       6.171   2.478   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.272   0.941   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.992   0.085   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.610   0.766   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.510   2.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.790   3.159   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.990   2.731   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.074   1.368   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.161   0.213   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.817  -1.288   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.944  -2.337   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.345  -1.740   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.033   2.185   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.204   2.863   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.321   4.227   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.288   4.196   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.636   1.296   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.078   0.755   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.275   0.397   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.268   3.824   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.465   4.793   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.359  -1.319   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.802  -1.224   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.073  -2.581   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.342  -1.177   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.653   0.260   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4   22   23                                             
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7   20                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   16                                                  
CONECT    8    7    9   13   19                                             
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    7                                                       
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    8                                                       
CONECT   20    5   21                                                       
CONECT   21   20                                                            
CONECT   22    3                                                            
CONECT   23    3   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    2                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
GA36	ChEBI

Chemical Formula

C₂₀H₂₆O₆

Average Mass

362.4220 Da

Monoisotopic Mass

362.17294 Da

IUPAC Name

(1R,2S,3S,4S,5S,8R,9R,12R)-8-formyl-5-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4-dicarboxylic acid

Traditional Name

(1R,2S,3S,4S,5S,8R,9R,12R)-8-formyl-5-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@]1([C@H]2[C@H](C(O)=O)[C@@]34C[C@@H](CC[C@H]3[C@@]2(CC[C@@H]1O)C=O)C(=C)C4)C(O)=O

InChI Identifier

InChI=1S/C20H26O6/c1-10-7-20-8-11(10)3-4-12(20)19(9-21)6-5-13(22)18(2,17(25)26)15(19)14(20)16(23)24/h9,11-15,22H,1,3-8H2,2H3,(H,23,24)(H,25,26)/t11-,12+,13+,14-,15-,18-,19-,20+/m1/s1

InChI Key

JZBLVVPDEDCVQA-SQLMURCQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	Plant	KNApSAcK
Cucurbita maxima	Plant	KNApSAcK
Dioscorea polystachya	Plant	KNApSAcK
Fusarium fujikuroi	Fungi	KNApSAcK
Psilotum nudum	Plant	KNApSAcK
Saccharum spp.	Plant	KNApSAcK
Sphaceloma manihoticola	Fungi	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
Dicarboxylic acid or derivatives
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Aldehyde
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:29595 )
C20-gibberellin (CHEBI:29595 )
Gibberellins (C11862 )
Gibberellins (LMPR0104170019 )

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	1.5	ALOGPS
logP	1.39	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.31 m³·mol⁻¹	ChemAxon
Polarizability	37.01 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000036

Chemspider ID

391669

KEGG Compound ID

C11862

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443455

PDB ID

Not Available

ChEBI ID

29595

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gibberellin A36 (NP0050183)

MOL for NP0050183 (Gibberellin A36)

3D MOL for NP0050183 (Gibberellin A36)

3D SDF for NP0050183 (Gibberellin A36)

3D-SDF for NP0050183 (Gibberellin A36)

PDB for NP0050183 (Gibberellin A36)

3D PDB for NP0050183 (Gibberellin A36)

SMILES for NP0050183 (Gibberellin A36)

INCHI for NP0050183 (Gibberellin A36)

Structure for NP0050183 (Gibberellin A36)

3D Structure for NP0050183 (Gibberellin A36)