NP-MRD: Showing NP-Card for Gibberellin A22 (NP0050178)

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Record Information

Version

2.0

Created at

2022-04-27 20:29:50 UTC

Updated at

2022-04-27 20:29:50 UTC

NP-MRD ID

NP0050178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A22

Description

Gibberellin A22 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 A22 is found in Canavalia gladiata . Gibberellin A22 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307222022452D          

 27 31  0  0  1  0            999 V2000
   -0.2125   -0.5590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7333    0.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240    1.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7872    1.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2074    0.7794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5081    1.4822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0913    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2676    0.1046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4352    0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670   -0.0036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -1.5143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1829    1.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079   -1.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960    0.5211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9960   -0.3038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9960    1.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146    0.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -0.7260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1558   -0.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4259    0.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4259   -0.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7186   -1.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511    0.0230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960   -1.1253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352   -1.9525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9  2  1  6  0  0  0
  6  2  1  6  0  0  0
  8 10  2  0  0  0  0
  1  9  1  0  0  0  0
  5 11  1  1  0  0  0
  6 14  1  0  0  0  0
  1 12  1  1  0  0  0
 12 13  2  0  0  0  0
 12 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  6  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  2  0  0  0  0
 20 21  1  6  0  0  0
 22 23  2  0  0  0  0
 17 26  1  1  0  0  0
 16  5  1  0  0  0  0
 17  1  1  0  0  0  0
 24 27  1  0  0  0  0
M  END


  Mrv1652307222022452D          

 27 31  0  0  1  0            999 V2000
   -0.2125   -0.5590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7333    0.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240    1.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7872    1.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2074    0.7794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5081    1.4822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0913    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2676    0.1046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4352    0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670   -0.0036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -1.5143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1829    1.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079   -1.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960    0.5211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9960   -0.3038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9960    1.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146    0.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -0.7260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1558   -0.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4259    0.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4259   -0.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7186   -1.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511    0.0230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960   -1.1253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352   -1.9525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9  2  1  6  0  0  0
  6  2  1  6  0  0  0
  8 10  2  0  0  0  0
  1  9  1  0  0  0  0
  5 11  1  1  0  0  0
  6 14  1  0  0  0  0
  1 12  1  1  0  0  0
 12 13  2  0  0  0  0
 12 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  6  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  2  0  0  0  0
 20 21  1  6  0  0  0
 22 23  2  0  0  0  0
 17 26  1  1  0  0  0
 16  5  1  0  0  0  0
 17  1  1  0  0  0  0
 24 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050178

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@@]3(CO)C=CC[C@@]21OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O6/c1-10-7-17-8-18(10,24)6-3-11(17)19-5-2-4-16(9-20,15(23)25-19)13(19)12(17)14(21)22/h2,4,11-13,20,24H,1,3,5-9H2,(H,21,22)/t11-,12-,13-,16+,17+,18+,19-/m1/s1

> <INCHI_KEY>
UPCTWJNMQCQZPT-AODVQFRNSA-N

> <FORMULA>
C19H22O6

> <MOLECULAR_WEIGHT>
346.3744

> <EXACT_MASS>
346.141638436

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.83062124984386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,8S,9S,10R,11R)-5-hydroxy-11-(hydroxymethyl)-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-12-ene-9-carboxylic acid

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
-0.010861725999999336

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.820322935721684

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.163478076231644

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9049282663722779

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
86.98269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8S,9S,10R,11R)-5-hydroxy-11-(hydroxymethyl)-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-12-ene-9-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUL-20         0                                  
HETATM    1  C   UNK     0      -0.397  -1.044   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.369   1.750   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.045   2.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.469   3.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.387   1.455   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.815   2.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.037   0.103   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.067   1.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.499   0.195   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.546   0.816   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0      -0.872  -0.007   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       0.080  -2.508   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.588  -2.827   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.075   3.653   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.948  -3.653   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.859   0.973   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.859  -0.567   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.859   2.506   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.201   1.740   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.201  -1.355   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.024  -0.134   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.528   0.973   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.528  -0.567   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.208  -2.881   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.895   0.043   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      -1.859  -2.101   0.000  0.00  0.00           H+0
HETATM   27  O   UNK     0      -4.546  -3.645   0.000  0.00  0.00           O+0
CONECT    1    9   12   17                                                  
CONECT    2    9    6                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    9   11   16                                             
CONECT    6    4    8    2   14                                             
CONECT    7    8    9                                                       
CONECT    8    6    7   10                                                  
CONECT    9    5    7    2    1                                             
CONECT   10    8                                                            
CONECT   11    5                                                            
CONECT   12    1   13   15                                                  
CONECT   13   12                                                            
CONECT   14    6                                                            
CONECT   15   12                                                            
CONECT   16   17   18   19    5                                             
CONECT   17   16   20   26    1                                             
CONECT   18   16   21                                                       
CONECT   19   16   22                                                       
CONECT   20   17   23   24   21                                             
CONECT   21   18   25   20                                                  
CONECT   22   19   23                                                       
CONECT   23   20   22                                                       
CONECT   24   20   27                                                       
CONECT   25   21                                                            
CONECT   26   17                                                            
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Canavalia gibberellin II	HMDB
GA22	HMDB
Gibberellin A22	HMDB

Chemical Formula

C₁₉H₂₂O₆

Average Mass

346.3744 Da

Monoisotopic Mass

346.14164 Da

IUPAC Name

(1R,2R,5S,8S,9S,10R,11R)-5-hydroxy-11-(hydroxymethyl)-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-12-ene-9-carboxylic acid

Traditional Name

(1R,2R,5S,8S,9S,10R,11R)-5-hydroxy-11-(hydroxymethyl)-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-12-ene-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@@]3(CO)C=CC[C@@]21OC3=O

InChI Identifier

InChI=1S/C19H22O6/c1-10-7-17-8-18(10,24)6-3-11(17)19-5-2-4-16(9-20,15(23)25-19)13(19)12(17)14(21)22/h2,4,11-13,20,24H,1,3,5-9H2,(H,21,22)/t11-,12-,13-,16+,17+,18+,19-/m1/s1

InChI Key

UPCTWJNMQCQZPT-AODVQFRNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Canavalia gladiata	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
Diterpene lactone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Primary 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	0.31	ALOGPS
logP	-0.011	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-0.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.98 m³·mol⁻¹	ChemAxon
Polarizability	34.83 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

HMDB0036891

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015851

KNApSAcK ID

C00000022

Chemspider ID

68024120

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101603107

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gibberellin A22 (NP0050178)

MOL for NP0050178 (Gibberellin A22)

3D MOL for NP0050178 (Gibberellin A22)

3D SDF for NP0050178 (Gibberellin A22)

3D-SDF for NP0050178 (Gibberellin A22)

PDB for NP0050178 (Gibberellin A22)

3D PDB for NP0050178 (Gibberellin A22)

SMILES for NP0050178 (Gibberellin A22)

INCHI for NP0050178 (Gibberellin A22)

Structure for NP0050178 (Gibberellin A22)

3D Structure for NP0050178 (Gibberellin A22)