NP-MRD: Showing NP-Card for Gibberellin A26 (NP0050179)

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Record Information

Version

2.0

Created at

2022-04-27 20:29:52 UTC

Updated at

2022-04-27 20:29:52 UTC

NP-MRD ID

NP0050179

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A26

Description

23365-02-8 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 A26 is found in Ipomoea nil , Ipomoea purpurea and Pharbitis purpurea. Based on a literature review very few articles have been published on 23365-02-8.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222292D          

 26 30  0  0  1  0            999 V2000
    3.2496    1.1589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2119    0.3347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5442   -0.1497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9673    0.6119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8168    1.5554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6287    1.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0055    1.5796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5844    0.8073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2216    0.2451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8670   -0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -1.4638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1503   -1.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    1.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7047    1.4920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3014    2.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8158    2.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5583    2.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575    0.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6844    0.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867    0.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254    0.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490    0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303   -0.8029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023   -0.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0013   -0.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0320    1.5221    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
  4  3  1  1  0  0  0
  4  5  1  0  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  2  0  0  0  0
 15 17  1  0  0  0  0
  7 17  1  1  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 20  1  0  0  0  0
  5 21  1  1  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 24  1  6  0  0  0
  2 25  1  6  0  0  0
  1 26  1  6  0  0  0
M  END


  Mrv1652304272222292D          

 26 30  0  0  1  0            999 V2000
    3.2496    1.1589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2119    0.3347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5442   -0.1497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9673    0.6119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8168    1.5554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6287    1.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0055    1.5796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5844    0.8073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2216    0.2451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8670   -0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -1.4638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1503   -1.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    1.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7047    1.4920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3014    2.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8158    2.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5583    2.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575    0.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6844    0.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867    0.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254    0.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490    0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303   -0.8029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023   -0.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0013   -0.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0320    1.5221    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
  4  3  1  1  0  0  0
  4  5  1  0  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  2  0  0  0  0
 15 17  1  0  0  0  0
  7 17  1  1  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 20  1  0  0  0  0
  5 21  1  1  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 24  1  6  0  0  0
  2 25  1  6  0  0  0
  1 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050179

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12[C@H]3[C@H](C(O)=O)[C@]45C[C@H](C(=C)C4)C(=O)C[C@H]5[C@@]3(C[C@H](O)[C@@H]1O)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O7/c1-7-4-18-5-8(7)9(20)3-11(18)19-6-10(21)14(22)17(2,16(25)26-19)13(19)12(18)15(23)24/h8,10-14,21-22H,1,3-6H2,2H3,(H,23,24)/t8-,10+,11-,12-,13-,14+,17+,18+,19-/m1/s1

> <INCHI_KEY>
MVHJDZCNXNYBEL-RQVJUCPVSA-N

> <FORMULA>
C19H22O7

> <MOLECULAR_WEIGHT>
362.378

> <EXACT_MASS>
362.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.69319045288826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5R,8R,9S,10R,11S,12R,13S)-12,13-dihydroxy-11-methyl-6-methylidene-4,16-dioxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
-0.5106283710000002

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.401286339802141

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.036118786124815

> <JCHEM_PKA_STRONGEST_BASIC>
-3.203323533566845

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
86.064

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,8R,9S,10R,11S,12R,13S)-12,13-dihydroxy-11-methyl-6-methylidene-4,16-dioxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic 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       6.066   2.163   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.996   0.625   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.749  -0.279   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.672   1.142   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.391   2.903   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.907   3.177   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.877   2.949   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.091   1.507   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.280   0.457   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.618  -1.299   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.891  -2.732   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.281  -2.186   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.086   2.218   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.315   2.785   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.563   4.225   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.523   5.520   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.042   4.342   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.601   1.185   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.144   0.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.162   0.415   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.661   1.548   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.265   0.131   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.857  -1.499   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.604  -1.618   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.469  -0.042   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.526   2.841   0.000  0.00  0.00           O+0
CONECT    1    2    6   26                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    4   22   24                                             
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7   21                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   17                                                  
CONECT    8    7    9   13   20                                             
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    7                                                       
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    8                                                       
CONECT   21    5   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22                                                            
CONECT   24    3                                                            
CONECT   25    2                                                            
CONECT   26    1                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₇

Average Mass

362.3780 Da

Monoisotopic Mass

362.13655 Da

IUPAC Name

(1R,2R,5R,8R,9S,10R,11S,12R,13S)-12,13-dihydroxy-11-methyl-6-methylidene-4,16-dioxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

Traditional Name

(1R,2R,5R,8R,9S,10R,11S,12R,13S)-12,13-dihydroxy-11-methyl-6-methylidene-4,16-dioxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@]12[C@H]3[C@H](C(O)=O)[C@]45C[C@H](C(=C)C4)C(=O)C[C@H]5[C@@]3(C[C@H](O)[C@@H]1O)OC2=O

InChI Identifier

InChI=1S/C19H22O7/c1-7-4-18-5-8(7)9(20)3-11(18)19-6-10(21)14(22)17(2,16(25)26-19)13(19)12(18)15(23)24/h8,10-14,21-22H,1,3-6H2,2H3,(H,23,24)/t8-,10+,11-,12-,13-,14+,17+,18+,19-/m1/s1

InChI Key

MVHJDZCNXNYBEL-RQVJUCPVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ipomoea nil	Plant	KNApSAcK
Ipomoea purpurea	LOTUS Database	35616633
Pharbitis purpurea	Plant	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
1,2-diol
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
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	0.06	ALOGPS
logP	-0.51	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.06 m³·mol⁻¹	ChemAxon
Polarizability	35.69 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00000026

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

101603110

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gibberellin A26 (NP0050179)

MOL for NP0050179 (Gibberellin A26)

3D MOL for NP0050179 (Gibberellin A26)

3D SDF for NP0050179 (Gibberellin A26)

3D-SDF for NP0050179 (Gibberellin A26)

PDB for NP0050179 (Gibberellin A26)

3D PDB for NP0050179 (Gibberellin A26)

SMILES for NP0050179 (Gibberellin A26)

INCHI for NP0050179 (Gibberellin A26)

Structure for NP0050179 (Gibberellin A26)

3D Structure for NP0050179 (Gibberellin A26)